We went from on-prem to cloud. Then came digital transformation, where every company suddenly needed to become a software company (whether they had any business doing so or not). Entire stacks got rebuilt - .NET stopped feeling inevitable, Python spread everywhere, and everyone got weirdly excited about Next.js. Mobile came in hot (B2B, naturally, is still deciding whether a phone is a real device). Recurring revenue became our SaaS religion. Remote work exploded, then partially un-exploded. Product-led growth rewired how companies scaled.

Each wave felt big. AI feels 10x bigger. And 10x faster.

That speed is the part I can’t quite process. There are days where it genuinely feels like I need a full-time job just to keep up with what’s happening. And even then, I’m not convinced I am. Am I just getting better at being slightly less behind?? Haha.

And that’s really the feeling underneath all of this: behind.

Not ‘I should probably test that new tool’ behind. More like ‘am I already operating on an outdated mental model?’ behind.

There’s also a weird social dynamic to this whole thing. Everyone has a system, a stack, a workflow that supposedly changed their life, saved them from the burnout, and probably whitened their teeth. It creates this illusion that everyone else already knows what’s going on.

So you hesitate to ask basic questions, because it feels like you’re the only dumb one who doesn’t get it.

Which is almost certainly not true. But it feels true. And the result is a lot of fake confidence theater, a lot of noise, and very little shared truth about what’s actually working.

Then there’s the part that’s harder to admit: a lot of what I spent the last decade learning is losing leverage.

Growth, marketing, product management, sales - these used to feel like crafts. You built intuition over years. You learned what great looked like. You got good at pattern recognition. You earned judgment and respect by grinding through it all.

AI is flattening a lot of that.

It’s a weird experience to spend ten years becoming excellent at something only to watch a 22-year-old produce a suspiciously solid version of it in 14 minutes. Not the best version. But enough to make you sit there like, wow, okay then. And you don’t really get to process that shift. There’s no mourning period. You just move on to the next thing, because everything is changing too fast. (and don’t even get me started on how non-tech people are supposed to keep up with any of this - ‘mass adoption’ feels almost comical.)

Which forces a much more uncomfortable question: if your identity was tied to being good at X, what happens when X gets automated?

Now, senior people still have some advantages, but some of the old signals of seniority are getting weaker fast. The hierarchy flattens. The ladder gets weird. Experience still matters, but not in the clean, linear way we got used to.

Honestly, I think that a lot of that is good. A lot of old hierarchies deserved to die. RIP politics and middle-management. Still, it’s disorienting as we are going through it.

And of course, the reward for becoming more efficient is exactly what it has always been: more work. If AI makes you 10x faster, nobody says, ‘Amazing. Please enjoy your afternoon!’ They ask why you’re not doing 10x more. Productivity gains get absorbed immediately by the system, which is very on-brand for tech.

And underneath all of this is the part we really don’t want to talk about: the economics.

If output goes up while the cost of producing that output goes down, what happens to compensation? What happens to leverage? What happens to the premium attached to knowledge work when more of that work becomes abundant? What happens to company structures when fewer people can produce dramatically more?

My guess is the value shifts.

Away from execution. Away from being the person who can grind through the work manually. Toward taste, judgment, prioritization, and orchestration. Toward deciding what’s worth building, not just how to build it.

Which sounds elegant until you realize those are harder skills to build patterns on and really really hard to teach/learn.

The last question I keep coming back to is whether we are the last generation that built our careers around software as a medium.

We leaned all the way in. We learned the tools, the systems, the playbooks. We rode cloud. We drove digital transformation. We built careers on knowing how to operate software better than other people. We are also, unfortunately, the sandwich generation that has to explain software to our parents and now AI to our kids.

But if software starts getting built, configured, and operated by AI, what happens to the people whose edge was being good at creating software?

I don’t know. And I’m not convinced anyone else does either, despite the amount of confidence cosplay happening online.

And maybe I’m overblowing it. Or maybe this is just what it feels like to live through a real industry shift while still being expected to perform like nothing has changed.

The only thing I feel confident about is that the advantage is shifting.

It’s shifting toward the people who can see clearly, choose well, and adapt faster than the ground is moving beneath them.

No pressure everyone. Everything will be okay. (RIGHT?)

I agree with the core premise of his article. Disruption is coming, and it’s going to be massive. But I think most people are framing the conversation the wrong way. Everyone is stuck debating whether AI will take their job. The answer is almost certainly yes (I know, I know - it’s terrifying). That part isn’t interesting anymore.

The more important question is this: What if this is also the biggest opportunity of your career?

Right now, there’s a short window where individuals can get absurdly far ahead by becoming AI-native. Not “AI-aware.” Not “occasionally uses Claude.” AI-native. And that window is measured in months, not years.

Who should actually be scared?

It’s a terrible time to be a company or an exec. But it’s a great time to be an individual contributor.

If you’re a founder/ceo or exec running a bloated, slow-moving org that spent decades layering process, coordination, and middle management to handle complexity AI is about to flatten, you should be sweating. Companies that need 26 meetings, four approval chains, and a Gantt chart from 2019 to ship a button color change aren’t careful. They’re exposed.

At this point, many companies are only alive because of distribution, network effect, or data lock-in. The product itself is no longer the moat.

But if you’re an individual stuck in a role you don’t love, underpaid, boxed in, spending your days in meetings that accomplish nothing, writing docs nobody reads, and waiting for your ideas to get prioritized on someone else’s roadmap, the bad news for them might actually be the best news for you.

The demand for AI-native employees is exploding. Not in some abstract, future way. Right now. Companies are starting to care less about fancy titles, perfectly laddered careers, and padded resumes, and more about who can actually get things done in this new environment. People with good taste, real business sense, and, most importantly, high drive. In the next year or two, I’m convinced being AI-native plus those qualities will matter more than years of experience, brand-name logos, or titles that only made sense in a slower world.

Let me make this concrete

At Lovable, we have a Slack channel called #feedback where anyone can post things that feel broken or annoying in the product. Normally, devs would jump in and fix them.

But lately, I started noticing something different.

Instead of devs writing the fixes, I kept seeing messages like, “Hey Cursor, fix this” or “Claude Code, can you handle this?” And then… the fix would just happen. A PR would appear. A quick human review later, it was live.

So next time I was ready to post in the channel (CTA button had the wrong color), I had a wild thought: could I fix this myself?

I don’t have an engineering background. I didn’t even have a GitHub account. But I remembered a teammate (Benjamin) I’d seen do this, so I asked him to show me how it worked. He helped me set up GitHub, Claude Code, and Cursor.

I took a screenshot of the button, told Cursor what was wrong, and asked it to fix it.

It immediately found the issue, fixed it, and opened a PR. The engineer reviewed it and merged it.

I had just “written” code to production. In minutes. Something that would normally take tickets, meetings, and weeks of waiting… I just did it. Not because I became an engineer, but because the gap between intent and execution collapsed.

Honestly, it felt like the biggest unlock for me since discovering Lovable. Equal parts excitement, an undeserved sense of superiority, and just enough danger to be intoxicating.

For individuals, this is leverage. And it’s happening right now.

This post is brought to you by Salespeak’s free new tool, IsYourWebsiteReady.ai:

AI agents influence buyer decisions without triggering analytics sessions.
ChatGPT. Claude. Perplexity. Already accessing your site.

Your analytics won’t show it. Agent Analytics does. Free.

👉 Reveal your AI activity

Get your head out of the sand

A lot of people’s response to AI right now is critique. Pointing out where it fails. Where it’s wrong. Why it’s overhyped. Screening for em-dashes. Every new model drop turns into a race to prove what it can’t do.

I get it. If something threatens your role, tearing it down feels like self-defense.

But that fear only makes sense if the current setup is worth protecting. And watching this play out, it feels like people are desperately defending a system that was already failing them. Meetings instead of making. Process instead of progress. “Work about work” that creates no value.

AI is not just automating tasks. It’s removing permission. You no longer need to wait for headcount, budget, or alignment to create something real. That’s why companies are nervous. A motivated individual with curiosity and initiative can now do what used to require a team.

This is why there’s a window right now.

Early adopters are compounding advantage. They’re learning faster, shipping faster, and building confidence faster. Once AI-native workflows become the default, that edge disappears. Right now, curiosity beats credentials. But that won’t last when AI skill becomes commoditized.

I’ve spent years writing about this stuff. About how full-time employment stability is a myth - were you 100% safe from layoffs, even before AI? About how tying your identity to your job title is a trap. How the leadership ladder has a dark side that pulls people away from work they actually love and into meetings, politics, and people management they hate. How I quit full-time roles to build career optionality - how owning your skills, your reputation, and your ability to create value independently is the real security. And how I literally want to eliminate my own job, because so much of Growth has been stagnating and I think AI could free us up to do better, more creative work.

Things you should do this week

First, lock in and try to vibe-code a rough version of your own company’s product. Block a few hours (using Lovable, obvi, LOL). No perfection. Just see how far you get.

Don’t start with edge cases or scale. Start with the core thing your product actually does. Most companies have two or three workflows that matter and a long tail of noise wrapped around them. Focus on those. See if your users can create their own personal tools solving for that workflow.

If AI gets you uncomfortably far in a single day, that’s a signal for you of what’s to come.

Second, make AI your default for everything. AI should be your starting point for everything: writing, thinking, designing, coding, planning.

The culture around this is backwards. We spend so much time shaming people for not deleting them em dashes... Oh how wrong we are here. The real question now is why someone didn’t use AI in the first place.

Manually doing work that AI can do better, faster, and cheaper isn’t craftsmanship. It’s wasted time. And in a world where leverage compounds weekly, wasting time is the most expensive mistake you can make.

Third, if AI couldn’t do something yesterday, try it again next week. AI improves in weeks, not years. Once AI began writing its own code to improve itself, the pace of capability growth went exponential. “We tried that and it didn’t work” is the fastest way to fall behind.

Fourth, start a side project. Not because you’re quitting tomorrow, but because building is the fastest way to internalize what’s changing. The tools are cheap or free. The barrier to entry is gone. Maybe you can even make money from it.

Fifth, ask the AI-native person around you for help. They’re waiting to show you. This stuff is contagious once you see it. Don’t do this:

Stop reading. Start shipping.

No one wants to lose their job. That fear is real. People depend on your income. I’m not dismissing that. But ask yourself honestly: do you love your job so much that you want it frozen exactly as it is? Do you want your kids to have it?

You need a job. But do you need this one, in this form, forever?

What if this moment isn’t about falling behind, but about finally getting unstuck?

The biggest risk right now isn’t AI taking your job. It’s watching other people pull ahead while you wait to feel ready.

So stop scrolling. Open Claude, ChatGPT, Cursor, or Lovable. Try something. It doesn’t have to be perfect. It doesn’t have to be big.

Just start.

Edited by Jonathan Yagel.

The pace is intense for two reasons: LLM capabilities are evolving faster than we can finish a roadmap cycle, and customer expectations are shifting right along with them. So it feels like we’re on a PMF treadmill. What used to be “horizon 2” innovation that companies had years to get to, we’re hitting every quarter.

There’s no playbook for that. No patterns to copy. And we’re doing it while the ground underneath us is also shifting: we are in the middle of the AI-driven technological platform shift all while distribution shifts are happening as well, and everything I thought I knew is being re-evaluated in real time.

Need to let go

I’ve spent my career in growth roles where 70-80% of what I already knew mapped to the new job. I’d show up, apply my frameworks, tune the funnel, build the loops, scale. All pretty straightforward.

This post is brought to you by Superinterviews: Join a FREE workshop on Nov 24th with me and the Superinterviews team on landing AI PM & GTM roles. Learn AI-native / AI-enabled frameworks, vibe-code with Lovable, and position yourself to win. Master interviews with real strategies from someone hiring right now. Save your spot now!

Lovable has been the opposite. Maybe 30-40% of my experience transfers. The rest I’ve had to unlearn. I’m having to let go of past patterns. Which is super uncomfortable. One of my superpowers is pattern recognition and building scalable frameworks from the trends I see. But the old structures are breaking apart. The market is just moving way too fast to rely on frameworks built for stable environments. So, now I have to treat all my hard-earned knowledge as disposable. Kind of sucks, right?

There’s an entirely new world of growth that’s emerging, and here’s what I’ve been seeing:

1. Growth works on new… ‘features’!?
   In previous roles, 90% of my job was experimentation and optimization. Here, most of the job is inventing entirely new loops, launching new initiatives, and creating new product surfaces (even, gasp, new features). We’re still defining how people use AI, not just scaling an existing behavior. The work feels closer to product innovation than funnel tuning.

2. Traditional marketing isn’t the lever
   Paid marketing, SEO, campaigns, nurture programs. They’re fine. They help. But they are not what moves an AI company right now. The real distribution is word of mouth, creator economy, and community. This all looks more like consumer growth patterns than traditional B2B. If your product isn’t getting talked about, there is no amount of optimization that can backfill that gap.

3. Growth surfaces are collapsing
   Most products are converging into a text box with an agent behind it. There are fewer knobs to turn on the surface. Growth work now sits deep in the agent quality, the model selection, the reasoning behavior, the personality. If the agent isn’t good, no onboarding flow will save you. So growth is embedded inside core product, not layered on top.

4. Need to be on the constant lookout for new growth channels.

   We are in the middle of the distribution shift and more than ever need to be constantly watching for new distribution windows opening. Will it be ChatGPT’s app marketplace? Will there be something with Sora? Who knows. But the point is that we are in the middle of the distribution collapse and changes are coming.

5. The AI skillset is crucial

   I sometimes reflect how different my days are now compared to say... 2 years ago. I’m constantly building something in Lovable, discussing my ideas with ChatGPT (from writing/clarity to brainstorming growth loops), trying out new AI features (hating most, loving others).

6. Growth is confusing during the PMF treadmill
   In past companies, finding product-market fit (PMF) meant you could move on to scaling and growth becomes the priority. Here, PMF is temporary, which means the growth/scaling stage is also… temporary and confusing. Every AI company is on this treadmill, whether they admit it or not. But we still have X,000,000 of paid users and millions in revenue to grow… What exactly are you scaling if product is changing so rapidly? I approach it by over-indexing on innovation and not optimization, but who knows if that’s the right path. My plan is to focus on more traditional growth optimization work when our PMF stabilizes.

7. Roles are blending
   We still have job titles, but the walls between them are thin. Designers do marketing. Marketers shape product direction. Engineers do product work. Everyone runs small feedback loops across their own work. The generalist mindset is necessary. People who only operate inside their lane move too slow for this environment.

8. Organizational structure can’t keep up
   The development velocity is too high for a clean process. You have to be comfortable in the messy middle. Plans are short. Ownership lines shift. You have to self-author your role day to day. This is not for people who want predictability. The current environment rewards people who can create clarity instead of waiting for it.

Those are the lessons, but what does this mean on a day-to-day level? Here are some specific shifts I’ve made to change how I work:

• Plan in 2-3 week directional bets, not quarters.

• Optimize for learning speed, not comfort.

• Default to shipping over polishing.

• Spend more time editing ideas than managing process.

• Assume my current mental model will expire soon.

The work is intense, fast, and constantly shifting. It’s the most fun I’ve had in years.

Whether you’re in AI or not, the growth game is changing. Now, the skills that matter most will be: Letting go quickly, re-learning faster, working across boundaries, and always building things people love enough to talk about.

If you’ve been in this field for a while, these probably don’t sound completely new. They’re a continuation of what we’ve all been doing. But they’re more essential than ever and it’s all speeding up. That’s the amazing/terrifying thing about growth right now: Everything is up for grabs.

What you make of this opportunity is up to you.

Edited by Jonathan Yagel, assistant to the regional meme-ger.

The AI gold rush is here. Companies are throwing money, power, and status at anyone who looks and smells “AI-native.” And guess who’s cashing in? Mostly men. Show me one woman-led AI acquihire with a disclosed, large price tag. Meanwhile, I can rattle off the male-led ones with rumored billions.

And listen, men - I applaud you for it. This isn’t a dig at you. This is a rallying cry for women to step up and claim our share of the future.

Let’s look at some stats:

• A global analysis found that women make up less than one-third of AI-skilled professionals. (Deloitte)

• In adoption of generative AI: U.S. data shows 33 % of women vs 44 % of men reported using or experimenting with gen AI in 2024. (Deloitte)

• Women are less likely to be in AI-augmented roles and more likely in roles vulnerable to automation: 57% of women vs 43% of men in jobs likely to be disrupted. (World Economic Forum)

And the gap is growing, because AI skills now show up everywhere. Here’s what I’m seeing in job listings:

• “Experience leveraging AI/LLM tools” - showing up in marketing, ops, and HR roles.

• “AI prompt design”- now required for content, UX, and even sales.

• “Cloud-based AI solution deployment,” “AI data pipeline automation,” “gen-AI workflow integration” - common in product and strategy roles.

• “Vibe-coding” - popping across product, design, marketing, and operational roles.

And women are quietly falling in the wrong group.

When I joined Lovable, I naively thought our user base would be 50/50 men and women (pink-and-purple brand with a heart logo should help, right!?). Wrong. Women aren’t even close to half our users - our best guess is around 20%. How disappointing is that? I kept asking myself, why? There’s no barrier to entry anymore. You can just show up and start building - no code, no gatekeepers. But still, no such luck.

Hard truth: women often need that extra push -a reason, an excuse, a shove out of comfort. But my fear? For too many, that push will come too late.

So we started SheBuilds on Lovable - a women-only buildathon to help close that gap. In our first cohort, nearly 3,000 women applied. 200 joined. Some built traditional B2B and B2C SaaS, but so many built products for elder care, kids, households, and community service - the kinds of problems traditional tech has ignored because they don’t fit the “VC-backable SaaS” mold.

Just look at what some women said about the experience:

YASSS!

Until now, building software was expensive. You needed deep technical skills or venture funding - both dominated by men. But today, the cost of building is close to zero. Anyone can create. Anyone can monetize. Anyone can win.

Now we can build software that’s hyper-local, hyper-specialized, and deeply tuned to the real problems in our communities. And women will lead this next wave - I know it. That’s just how our brains work.

But we need women to start exploring it now, because if we don’t seize this window, we’re going to watch the gap widen all over again.

Now some may say: “It’s early, women can catch up later.” That’s wishful thinking. Early adoption sets hierarchy. The people experimenting now become the default “AI experts” later - and that title compounds into promotions, equity, and power. Miss this wave, and you’re not behind for a year - you’re behind for a decade.

Others may say: “AI tools are easy - no need to worry.” There’s a difference between using AI and building with AI. Prompting ChatGPT isn’t the same as creating an app, automation, or model. Users don’t shape the market; builders do.

Here’s what I know: this moment could unlock the biggest wave of women builders in history - if we lean in now. We can build software that solves problems the world has ignored, and we don’t need to chase unicorns to do it. We can create a new generation of “mom-and-pop SaaS”- profitable, independent, purpose-driven.

And the best part? It can give women something we’ve been fighting for all along - solopreneurship path with purpose, balance, and control. Control over your schedule. Over your income. Over your life. The kind of independence every mom dreams about.

But if we hesitate, AI becomes the next boys’ club.

So here’s my call:

• Women - lean in. Get curious. Build something with AI… *anything*.

• Grab another woman and pull her in with you.

• Men - keep leading, but help open the door wider.

Because this isn’t just about equality. It’s about economic survival. The people who build the future own it.

Tips on how to start:

• Build a tutoring app for your kid’s weakest subject (I built one for my son in ELA).

• Build your personal site - your “AI-native” resume (here is mine - you can remix it)

• Anything that is annoying to you - go automate it with AI.

Remember, you need to treat AI like a career accelerant, not a curiosity. List concrete AI skills on your resume and use them in interviews. Employers are already paying premiums for “AI-native” experience.

And if you want community, join our next SheBuilds on Lovable cohort this December - 48 hours of women-only building, unlimited credits, and real collaboration. Follow me on LinkedIn for an announcement later this week or jump onto our waitlist NOW.

(Also… we’re planning HUGE SheBuilds on March 8, International Women’s Day. Want to join the cause by sponsoring, mentoring, or volunteering? Comment or reply)

Because this time, we’re not asking for a seat at the table.
We’re building a new one.

The first 3 months of a new job are always tricky, needing to balance learning with delivering. And if you’re in growth, PM, marketing, or sales… the “first 3 months is just to onboard” phase? Yeah, that luxury doesn’t exist. If you’ve actually had a full 90-day ramp with no pressure to deliver - I’m impressed. Teach me your ways.

This post is sponsored by Uptempo! Growth moves fast. Your plan should too.

Halfway through the year, you can’t afford slow reforecasts or scattered plans. Uptempo connects your plan, budget, and performance in one system -so you can pivot fast, optimize spend, and prove impact.

Teams at HubSpot, Unilever, Workday use Uptempo to reforecast in hours, not weeks- and shift spend where it drives results. See how Uptempo works →

If you over-index on action, you’ll likely misfire because you’re missing context. But if you over-index on just learning, you’ll create anxiety and unmet expectations around you (because they hired you to deliver… and revenue forecast is not known for it’s patience).

It’s a tough balance to strike. Assuming you are learning at max velocity, here is how I deal with ‘take action’ part: start with protecting what’s already working, move onto quick wins, go after big bets, and finish with the strategy.

1. Protect what is working now

On day 1 I focus on protecting what’s already working. This is the fastest way to learn existing business too.

If something is driving results, your first job is to identify it and NOT MESS IT UP. Then, if possible, remove friction to make it work even better.

What it looked like at Lovable

1. Lovable has serious word-of-mouth momentum. Within a few months, it had built a passionate community of users who genuinely love talking about the product. That kind of emotional connection is rare in SaaS, especially in B2B. But it didn’t happen by chance, it’s in their DNA. From day one, the goal was to build the most lovable product on the market. That means no shortcuts, no broken flows or mediocre experiences. Every detail is intentional.

2. Influencer marketing was working well, but had no clear owner. One of my first moves was to hire someone to take full ownership of the program and grow it.

The best way to figure it out? Talk to everyone and ask, “Hey, what’s working?” Or in my case, “Hey, why are we growing?” You’ll get a bunch of different opinions, but patterns will start to emerge pretty quickly.

2. Find the easy wins

From days 2 to 30, it’s time to start tackling those “quick” wins. I define quick wins as something I’m 80% positive will have a positive impact based on my previous patterns. Most often I’d classify this steam as ‘optimizations’. Here is how I identify them:

1. I think about my past experiences and think about what tactics have copy/paste potential.

2. At the same time, I move quickly through the product with fresh eyes, spotting areas of opportunity before I get lost in the weeds.

3. Lastly, I ask everyone - if you were in my shoes, what would you do? Have your pen ready, because there will be a ton of great ideas thrown your way.

For Growth, this often looks like optimizing key pages, improving onboarding, doing pricing page improvements, introducing trials, testing new paid channels, or tightening up analytics.

What this looked like at Lovable

1. Finding obvious optimizations across variety of pages (home, pricing, dashboard, etc), onboarding and cancellation flows.

2. Because word of mouth was already strong - and our freemium users weren’t contributing enough to our growth loop - spinning up a referral program felt like a no-brainer to lean into PLG virality. (And yes, I took inspiration from Dropbox)

3. We were running paid search (SEM) but hadn’t properly explored organic search (SEO). If you’re doing SEM, you should be doing SEO too. So we signed contract with an agency to get started right away. Low effort, clear upside, zero reason to wait.

4. Launching annual plans and introducing rollovers (both to improve retention) were also immediate strategies that just made sense based on my past experiences.

3. Look for a big bet you want to take

As day 30 approaches, it’s time to start thinking about a few bigger bets - the kind that have a real shot at driving step-function change (and let’s be honest, they’re way more fun to work on). By now, you should begin having some sort of grasp of the context and how the business actually works - what matters, what doesn’t, and where the real levers are.

Key word: thinking. This isn’t about committing yet - it’s about shopping the idea around, stress-testing it, and asking people why it wouldn’t work. If your first idea doesn’t stick? No big deal. Move on. The goal is to fine-tune your intuition by absorbing other people’s context.

What this looked like at Lovable

Lovable has product-led growth model, meaning growth should come from the product itself, not just from marketing and sales.

But one thing stood in the way: virality and adoption was limited because collaboration was locked behind the highest paid self-serve tier. This is something I repeatedly preach against, as I’m a big believer that collaboration should be part of the free experience. You build in teams, and bringing people into the product shouldn’t be gated - all of those are inputs into delivering some output in your product. So gate output (credits in Lovable case), not inputs. So we gate roles and permissions, privacy settings, and admin controls, but not collaboration.

So I proposed making collaboration free and began shopping it around. Got zero objections and lots of encouragement - so we pushed forward. And just a few weeks later… it’s live! Now, thats a wildly fast turnaround for something that would normally take many many months. But hey, the Lovable dev team is ahmazing and they crushed it.

Full disclosure: normally I’d wait longer before making a move this big, but with such strong alignment and extremely high conviction on my side, I decided it didn’t make sense to sit on good bet. And yes, our invites nearly 10x, so it worked! But now there are many optimizations that have to take place to make it 100x.

4. Start shaping the strategy

Somewhere between day 30 and 90 I start thinking about overall strategy.

I open a Miro board and note rough strategic bets, things that feel directionally right, even if they’re still only half-formed in my head and need plenty of confirmation.

The goal is not to act on them right away but to document what I see before I lose perspective. Because let’s face it, the outsider lens fades fast.

The deeper you go inside a company, the harder it becomes to see the product like a customer. That’s why I start early, and keep it open. Most of my initial instincts land about 60–70% right. The rest get shaped by what I learn. But without that early draft, I’d have nothing to refine.

What this looked like at Lovable

At Lovable, my early instincts included:

• Building a founder ecosystem

• Doubling down on community

• Kicking off integration strategy

• Standing up student, non-profit, kid, and [insert specialized user segment here] programs

Will these bets hold up? Ask me again next year. But generally speaking most of these should see a day of light. (If you’re curious to see how they evolve, keep an eye on what we roll out at Lovable)

A note on operational leverage

In parallel to everything else, I look for changes that make the entire organization more effective. Think of it as operational improvements: less about customer output, more about how we work. This includes new rituals, documentation, roles & responsibilities, etc.

What this looked like at Lovable

1. Introducing release tiering system: There were constant releases going out (omg can Lovable ship!), but no way to know how much marketing or growth support each one needed. So we introduced a simple tiering model:

   1. Tier 1 = major release → full go-to-market support

   2. Tier 2 = moderate impact → lighter push

   3. Tier 3 = minor update → changelog only

2. Use case mapping: Everyone kept referencing our ICP but nothing was documented. So I quickly built a use case map outlining motivations, jobs to be done, usage frequency, and alternatives. Once shared, the team aligned fast: yes, that’s who we’re building for.

3. Pricing & packaging source of truth doc: We had a lot of drift around how we decide what goes into which plan - some confusion around pricing, packaging, and unspoken exceptions. This doc brings clarity, alignment, and a single place to reference when making decisions or communicating changes.

And another side note: interim engagements

Everything I’ve shared so far applies to full-time roles, when you're coming in to define the roadmap, build the team, and steer the long game.

Interim roles are different.

You’re not there to discover what’s broken. You’re there to fix it. Fast.

• I joined Miro after a rebrand tanked their brand SEO, which represented over 30% of their top-of-funnel traffic. The job? Recover it.

• I joined Amplitude when they had a freemium model but lacked self-serve monetization. My job was to ship it within six months.

When you’re an interim, the order of points 1 and 3 shifts. It becomes:

1. Work on the big bet

2. Find the easy wins

3. Double down on what’s working

4. Shape the strategy

Interim work should always be tightly scoped. If the company can’t clearly articulate what they want you to fix before you join, don’t take the job. You don’t have any time to “figure it out.” You have 6–12 months to ship the solution.

Anti-patterns to avoid in your first 90 days

A few traps I’ve seen (and occasionally fallen into myself):

• Overpromising early wins: It’s tempting to try to prove your worth immediately, but setting unrealistic expectations - especially before you understand the context - usually backfires.

• Shipping without alignment: Moving fast is good. Moving fast without syncing with stakeholders? Not so much. You’ll waste cycles and erode trust.

• Fixing things that aren’t broken: New eyes can spot issues… but sometimes what looks broken is working just fine for reasons that aren’t obvious yet. Ask first, fix later.

What to do if nothing’s working

Not every team has momentum. Sometimes you walk into a broken funnel, unclear positioning, or no product-market fit. If that’s the case:

• Focus on unblocking one core user path - even if it’s small, a clear focus builds confidence and momentum.

• Rally around one core metric that matters. If you try to fix everything, you’ll fix nothing.

In messy environments, narrowing your scope is the fastest way to create clarity.

And good luck!

Edited with the help of Diana Bernardo.

Lovable is blowing past crazy revenue milestones: $1M ARR in just 8 days post-launch, $17M in 3 months, $60M in 6 months, and $80M ARR in just 7 months. With ~35 people. That’s not a typo. That’s the new normal - if you’re AI-native. And I don’t just mean the product is AI-native. I mean the people are.

What even is an AI-native employee?

Before Lovable, when someone said “AI-native,” I assumed they meant the product. Built with AI at it’s core. Agent workflows. GPT something-something. But after getting in the trenches here, I’ve realized: the product being AI-powered is only half the story. The real shift is how people work.

An AI-native employee isn’t someone who “uses AI.” It’s someone who defaults to AI.

Typical tech company: a case study in bottlenecks

Let’s rewind to the traditional tech org.

You have an idea. Great. Now you need either money or people to solve it. It goes something like this:

Step 1: Craft a beautiful doc… that nobody will read.

Step 2: Sit through 26 meetings, syncs, check-ins, standups, and “quick connects”… that accomplish absolutely nothing.

Step 3: Submit a request to design… that goes into the bottom of the backlog.

Step 4: Beg for budget to maybe, just maybe hire a contractor who might be available sometime this quarter… just to enter endless conversations with Finance about ROI.

Step 5: Ping web dev to squeeze it into this sprint… so they can laugh at you.

Step 6: Wait… while pretending the Gantt chart isn’t six weeks out of date.

[Bonus]: Discover - surprise! - there is tech debt. Add 8 months to your delivery.

Step 7: Finally ship something so scoped-down, so watered-down… that it barely resembles your original vision.

Sound familiar? Yeah. That’s the cost of dependency drag. Specialization is great until it becomes a coordination tax. Enter: ops teams and managers to manage the mess.

And just like that, your velocity dies.

AI-native org: default to done

Now let’s talk about how AI-native employees do it (as seen at Lovable)

Here, when someone wants to build something (anything) - from internal tools, to marketing pages, to writing production code - they turn to AI and... build it. That’s it.

No headcount asks. No project briefs. No handoffs. Just action.

At Lovable, we’re mostly building with… Lovable. Our Shipped site is built on Lovable. I’m wrapping hackathon sponsorship intake form in Lovable as we speak. Internal tools like credit giveaways and influencer management? Also Lovable (soon to be shared in our community projects so ya’ll can remix them too). On top of that, engineering is using AI extensively to ship code fast (we don’t even really have Product Managers, so our engineers act as them).

Can everything be done this way? Absolutely not. But even when we do go cross-functional (aka my design and dev teams jump in), things still move at crazy speed - because everyone’s using AI to cut the fluff, skip the handoffs, and just… get things done faster.

Will it change as we grow? Maybe. But right now, this feels very different from any other startup of similar size I’ve ever encountered.

Spotting the ai-native in the wild

Most (not all) of the AI-native employees I’ve seen are young (at least compared to me, LOL) - fresh out of school, sometimes not even graduated yet. And honestly? That’s their superpower. They haven’t been indoctrinated with our corporate bullshit. They’re not weighed down by legacy processes, approval chains, or the deep-rooted belief that "things just take time." They see a problem and start building.

So what changes?

1. Ownership is real: You build it? You own it. No “well leadership changed the scope” excuses. It’s your idea, your execution, your result.

2. Autonomy is unlocked: There’s no need to wrangle five other teams. You can just go. And that freedom is addictive.

3. Trust becomes the backbone: You can’t move this fast without implicit and explicit trust. If you need a weekly check-in to approve button colors, this ain’t your speed.

4. Velocity becomes your moat: When the whole company moves like this, it stops being a team dynamic - it becomes cultural gravity. And customers feel it.

Proof and point on velocity: in the five weeks since I joined, we’ve shipped a referral program, launched free collaboration, and in just a few days, annual plans and credit rollovers will be live. And that’s only a highlight reel - there are countless improvements and optimizations that happened in between. This is just growth, I’m not even talking about our core team. Again, remember - 35 people total!

The hidden superpower: cheap failures

When you can move this fast, the cost of failure plummets. That means:

• More bold bets.

• Less analysis paralysis.

• And a wild, unfair advantage in learning loops.

“Move fast and break things” is back - but this time with 10x output and 1/10 the mess.

But what about the jobs?

Cue the naysayers:

“But the process is good, it helps us stay aligned!”

Sure - if by “aligned” you mean equally stuck. Attaching yourself to process is just trying to validate your own existence and hard earned experience. Don’t do it (but I appreciate it’s painful). Adapt to the new norm. Let velocity lead, and introduce process only when (and if) it’s actually needed.

“Won’t this kill jobs?!”

Most jobs are just fine. Ya’ll just need to maintain your vertical expertise and learn to work with AI. But me be crystal clear, I think some jobs will disappear:

• Operations roles that only exist to herd cross-functional chaos? Gone.

• Managers with no vertical skill, acting as coordination layers? Extinct. And thank goodness.

We’re not replacing people. We’re replacing bloat. The rise of AI-native employee means the fall of organizational calories that don’t create value.

AI-native employees can’t survive in legacy systems

AI transformation inside existing tech companies is going to be brutal. You can’t just spin up a centralized “AI task force” and expect the rest of the org to suddenly think and operate differently. It doesn’t work.

This mindset shift isn’t something you can document or mandate - it has to be seen and experienced. I know, because I had to see it myself.

And even if a few brave AI-native employees emerge, the existing bureaucracy will smother them with a thousand tiny cuts: “Did you get that approved?” “Who signed off on this?” “Let’s run it through the process.”

Congrats, you just killed the spark before it had a chance to catch fire.

The future, in one hot take

Here’s my bet:
→ Company sizes will shrink.
→ Org charts will flatten.
→ The middle management layers without vertical expertise will vaporize.
→ The AI-native employee will become the new 10x team.

Welcome to the future #AINativeEmployeeEra

I’ve been fairly open about my career journey - if you’ve followed me for a while, you know this isn’t my first time walking away from traditional employment (read: why I quit full-time roles). I first made the leap into solopreneurship six years ago, after realizing that the full-time leadership path I had fought hard for was actually pulling me away from the work I loved most.

And so I went ‘solo’: built a portfolio of work around my skills, and learned how to grow a business around my own product, which is my brain. Everything was ahmazing, but then boom - I grabbed a full-time opportunity with Dropbox (read: Why I ‘un-quit’ full-time roles) that led people to ask questions, the most pressing being “Is solopreneurship dead?”.

Solopreneurship is not dead. It’s so alive that I just jumped straight back into it.

Is full-time employment dead?

Haha, not quite. But it is evolving, and faster than we may think. Although I left Dropbox for traditional reasons (a change in company priorities), there’s a fundamental shift happening in our space. Just look at Shopify - they’ve already made it a requirement that any new role must be justified by proving AI can’t do it first.

In tech, we’re quickly moving toward a future where many of our very own traditional full-time jobs may not exist. We all know it’s happening - we see the cliff ahead, we’re talking about it, we’re even scared of it - yet we’re still collectively accelerating toward it. And yes, the institution (companies, investors, and the market) is applying an intense amount of pressure to that acceleration pattern, forcing us to make AI smarter, faster, and cheaper. But instead of pushing back for the sake of our own well-being and survival, we’re very much playing along.

Similar patterns showed up in the past, just take industrial revolution as an example, but this is the first time I’m living through one. And yeah, it’s wild.

Which is why I’m doubling down on the biggest career flex out there: career optionality. In this economy, you probably should too.

Full-time employment: the stability myth

Most people equate a full-time job with stability, and so they gravitate towards it. But that’s just not true.

Especially in U.S., where employment is at-will, a contract doesn’t protect you. You can be let go at any time, for any reason, or for no reason at all. And even in countries with stronger labor protections, companies restructure, priorities shift, and headcount gets cut. We’ve all seen it happen all too often recently with waves of layoffs across our industry. And this is just the beginning. More and more companies will experience product-market fit collapse, and your full-time job could disappear before you even see it coming.

So when people tell me that solopreneurship is risky, I very much disagree.

Building a diversified business around your skills is actually the most secure way to work. You own your skills, your reputation, and your distribution. To me, that looks like security.

And yes, the transition at the beginning is tough. The first six months of my solopreneurship journey were brutal - both for my sense of identity (who am I without a full-time job??) and my financial stability (when or where will the next client come from??). But once you build a baseline, you’re no longer dependent on someone else to decide whether or not you get a paycheck. You’re not on a short leash with the market anymore. You have options, leverage, and you’re building something that can catch you, no matter what happens.

The ultimate goal: career optionality

Ask most people about their career goals, and the answers will revolve around titles: “I want to reach Director level”, “I’m gunning for the CPO position”, “I want to start a company”.

All valid aspirations. My personal goal was to get to VP level as fast as possible. And as I quickly found out, this is also one of the fastest ways to accidentally start hating your life.

I know because I was there.

On paper, everything may look great: fancy title, great logo, big team. But what you end up doing in those positions is not nearly as glamorous - unbearable stress, terrible sleep, long working hours, meetings galore, and lots and lots of people problems (he said what in the meeting!?). I had no time for my family, and my health was deteriorating fast.

So I asked myself: “If I forwarded myself 15 years and looked at myself right now, would I be proud of my decisions or resent them?”. You probably know the answer because you know what happened next: I got rid of my golden full-time handcuffs and started my solopreneurship journey.

Along the way, I realized the ultimate career flex isn’t building someone else’s dream, chasing a title, or flying first class to company off-sites. It’s having career optionality - being in a position where full-time roles are just one of many ways you can engage with the market, not the only way and definitely not a requirement.

Is this me urging you to become a solopreneur tomorrow? No.

It’s just me suggesting you should start asking yourself regularly: Does this year working in this position help unlock new options for me? When you’re taking on new responsibilities, validating a recent promotion, or developing skills you can market later, for example, you’re building optionality.

But if you’re doing more of the same, with no growth in sight, the time investment is simply not worth it. It’s wise to start thinking about how to unlock new opportunities. That could mean taking an advising client on the side, switching jobs, switching departments, or even starting to share your knowledge online.

That said, I don’t recommend jumping into solopreneurship too early in your career.

You still need to build credibility and find your own personal product-market fit. Early roles are where you validate that people are willing to “buy” your thinking, either by hiring you, promoting you, or asking you to lead harder problems. That validation is what makes it easier to sell your skills later on.

Going solo ≠ forever closing the door to full-time

There’s a general misconception around the idea that once you go solo, you’re forever stuck outside of the walls of a “real job”. Again, not true! In fact, I get more full-time opportunities as a solopreneur than I ever did when I was in a traditional full-time role.

Increasing the variety of experiences under your belt doesn’t close doors, it opens more of them. When you see the inside of more companies and gather more data points, you’re strengthening your position as an expert.

Solopreneurship isn’t a rejection of full-time work, it’s just a different way of participating in the market. One that gives you more choices. You can take on an interim role, have advisory engagements, consult, run workshops, build courses, and write. Yes, you can even get a full-time job if the timing and the scope feel right.

And when one type of engagement doesn’t feel right anymore? You walk away with the same peace of mind that you walked in.

Where I see us heading

Having a full-time job or not is not a black and white discussion. The grey area in between is usually related to the career stage you’re at, and the circumstances of your personal life.

But one thing is becoming increasingly clear: the era of long tenures and static roles may be coming to an end, as AI accelerates everything. Innovation speed is increasing, priorities shift faster, teams reorganize more often, and the types of problems companies need solved change at accelerating speed.

In this new world, employment may starts to look a lot like a subscription: companies bring you in when they need your skills, and cancel when they don’t.

What does that mean for you?

It means you need to know your superpower and build a system that helps the right companies find it. Whether or not you ever end up going solo is up to you. But everyone should be building the same thing: a system that gives you leverage, protects your independence, and keeps your skills relevant, no matter how fast the world changes.

That’s what I’ve built. That’s what I’ll keep building. And that’s what I want for you too.

If you have the opportunity to be more intentional about your next move, this post will break down different company archetypes and what each one can do for your career.

Six most common archetypes

I see the following as the most common company archetypes:

Let’s go through each one.

Archetype 1: Unicorns

These companies are fast growing scaleups. They are typically <200 employees large, generate $50-100M in revenue, and are growing at a blistering ~100% year-over-year. Think Miro, Figma, and Slack in their early days or Clay now. Joining one of these is like strapping yourself to a rocket — thrilling, high-speed, and terrifying. Burnout is almost guaranteed, but the experience will be one you talk about for the rest of your career.

You won’t necessarily learn much in the traditional sense because everything is moving so fast and up to the right. Mistakes often go unnoticed as long as the growth keeps compounding. If you flourish in chaos, can handle being overwhelmed, and enjoy wearing multiple hats, this is the place for you.

• Work Environment: Most of your time will be spent figuring out why the business is already growing and removing obstacles in its way. Hiring aggressively, putting processes in place (without killing the momentum), and constantly re-adjusting to new realities.

• Challenges: One of the toughest aspects? People get outgrown fast. Not everyone can evolve and adapt quickly enough to keep their jobs. A director at a $50M company is very different from a director at a $150M company — and in these businesses, that transition could happen in just a year.

• Career Impact: If you survive, having “founding team member at a unicorn” on your resume opens a lot of doors.

• Your Seat at the Table: Medium-sized. You’ll have visibility into strategic decisions, but good luck influencing them unless you’re in the core leadership circle.

I’ve experienced this environment at Miro. My workdays started at 5 AM and never really ended — it was an “always-on” role. Things were happening at an astronomical speed, and all I was trying to do was keep up. I dreamt about work and often woke up at 3 AM just to finish sending Slack messages that were stressing me out. The ride was exhilarating but mentally and physically taxing. I wouldn’t trade my time there for anything, but I’m not sure I have the energy to do it again.

Archetype 2: Tankers

These are your Googles, Apples, and Microsofts. 100,000+ employees, billions in revenue, and growing at a steady 5-15% annually. These companies run like well-oiled machines — meaning every role is hyper-specialized and your job is to stay in your lane.

• Work Environment: Here, you’re part of a massive ship that’s already on its predetermined course. The politics and tech debt are legendary and progress happens at a glacial pace. On the plus side, you get to see what true scale looks like.

  

• Challenges: It’s slow and steady for a reason. Very measured decision-making and lots of “work about work” can feel like death by a thousand cuts.

• Career Impact: These companies are great places to start your career, offering plenty of training resources and oversight. Career growth is doable, but outcomes are not valued as much as mastering the art of managing up and navigating internal bureaucracy.

• Your Seat at the Table: Don’t expect to drive major change — your seat at the table is tiny, possibly in a completely different building.

It’s worth mentioning that these companies pay exceptionally well. If financial stability and benefits are your priorities, these are the places to be.

Archetype 3: Declining Giants

These are the once-mighty corporations that are now struggling to grow. Think IBMs and Yahoo’s of the world. They have thousands of employees and have only one goal: need to re-accelerate growth. The problem? Years of bureaucracy, aging infrastructure, and an ingrained resistance to change. But this is where you can truly sharpen your ability to execute, adapt, and lead through uncertainty.

• Work Environment: Full of reorgs, strategy pivots, and leadership shake-ups. If you like change, buckle up — these places never stop changing.

• Challenges: The challenge here is execution: every mistake (and win) is highly visible. There’s no coasting. You either deliver results or you don’t last.

• Career Impact: Career opportunities are big since turnover is high. If you play your cards right, you can climb the ladder quickly. But mentally, this is a different game. Whereas a unicorn changes to support massive success, a declining giant changes out of desperation. Playing to win versus playing not to lose are two different games.

• Your Seat at the Table: Surprisingly large — because anyone who can actually drive results is desperately needed.

Archetype 4: Survival mode

These are the earliest-stage companies still searching for product-market fit. Think pre-Series A startups with 10-50 employees, maybe a million in revenue (if that), and a whole lot of uncertainty.

• Work Environment: These are arguably the most stressful companies to work at. Every decision could be life or death for the business. You’re expected to do everything because no one else is around to do it. Chaos is the norm and structure is a distant dream but autonomy is high.

• Challenges: The biggest risk? The company might not make it. Many don’t.

• Career Impact: If you have no problem with ambiguity, enjoy building things from scratch, and want to develop a ridiculously broad skillset, this can be a career-defining experience. I would not recommend these for anyone early in their career — there’s no mentorship or structured learning environment here.

• Your Seat at the Table: Massive. In fact, you might be the one building the table. However, your comp is non-existent and likely loaded with equity that may or may not materialize into anything meaningful.

Archetype 5: Lifestyle Boats

These are often founder-led, bootstrapped, profitable, and optimized for sustainable growth. Think Basecamp or Mailchimp before the acquisition. These companies aren’t in a rush to scale at all costs.

• Work Environment: Expect to wear multiple hats, but in a far more controlled and less chaotic environment than a unicorn or early-stage startup.

• Challenges: Work-life balance is often better, but career acceleration can be slower since these companies don’t have the same “exit at all costs” mentality.

  

• Career Impact: You get a first-hand look at how sustainable businesses operate. Mentorship and strong work relationships within your team and with business partners might be more inherent.

• Your Seat at the Table: Medium-sized, but heavily dependent on company culture. Some founders keep things tight, while others encourage collaboration across teams.

To me, this was SurveyMonkey during the seven years I was there. It had a leadership team with multiple success stories under its belt, a willingness to invest in the team, and a capability to drive sustainable growth without any VC pressure. There was undeniable pressure to deliver results, but it came with plenty of support and reasonable timelines. These environments are fantastic places for people early in their careers.

Archetype 6: Social Good Seekers

These are companies where impact is prioritized over revenue. Think Patagonia or smaller nonprofits focused on climate change, education, or social justice. If making a difference is your primary motivator, these environments can be incredibly fulfilling.

• Work Environment: Resources are often scarce and scaling impact without scaling funding is an ongoing struggle.

• Challenges: Salaries may not be as competitive as in the private sector, but job satisfaction can be high if you believe in the mission.

• Career Impact: The opportunity to make tangible contributions to causes you care about can be deeply satisfying. You’ll learn how to be strategic and “do more with less” — which is true of almost all companies anyway — but it’ll more personally align with your values and passions.

• Your Seat at the Table: Often larger than expected, especially if the organization is smaller. You may have a say in big decisions, but expect constraints around execution due to funding limitations.

Evaluating Company Archetypes

To understand which archetype a company falls into, ask the following questions:

1. How many employees does the company have? (This one is easy.)

2. What has been the year-over-year revenue growth for the past three years? Private companies might be cagey about this, but if they don’t share it after you sign NDA, that’s a red flag.

3. How much runway does the company have? Everyone can say they’re on “the path to profitability,” but find out how long they have before they need to raise another round to sustain operations. You don’t need exact financial numbers, but try to get a ballpark estimate (months, quarters, or years).

Know Thyself

There’s no denying it — the market is rough right now. But at the end of the day, you still need to be clear on what you want and which company archetype will be the best fit. Or at the very least, go in with a clear understanding of what to expect so you can set realistic expectations. Here are some key questions to ask yourself:

• How tolerant am I of change? If you prefer a steady pace with little change, lifestyle companies or slow and steady tankers might be ideal. Scale ups or companies in transition (unicorns or declining giants) undergo TONS of changes.

• How much pressure can I handle? More specifically, how much *negative pressure* can you take? Think incredibly tight deadlines, lots of thrashing, less work-life balance. This isn’t about questioning your ability to “handle your sh*t” but recognizing that companies on a downward trend or in tough industries may not align with what you’re looking for at the moment (and there are a lot of them out there).

• Are clear roles and responsibilities important to me? The less established a company, the less clarity you’ll have around roles and responsibilities. For some, this ambiguity is exciting. For others, it might not be worth the added stress.

• What’s my financial priority? Yes, it can just be about the money — depending on your personal circumstances and phase of life. If you need immediate financial security, you should probably skip the startup offering you the potential of a higher payout (read: equity) instead of a higher base salary.

Final Thoughts

Choosing the right company archetype depends on your risk tolerance, career goals, and appetite for chaos. Some people thrive in fast-growing scaleups, while others prefer the stability of an established giant. No one path is better than the other — it’s all about what you want out of your career.

But one thing is certain: knowing what you’re signing up for is half the battle.

Edited with the help of Melissa Halim.

If any of the links don’t work, it means the company has taken the job down.

1. Superhuman is hiring for a Director, Growth Product

I used to despise email until I started using Superhuman. I’ve advised them and am an avid super user of their product. I would highly recommend this role to anyone.

→ Job description

2. Gitlab is hiring for a Director, Growth Product

I’d be all over this one. GitLab is a great company and has produced incredible growth leaders in the past.

→ Job description

3. Atlassian is hiring for a Sr. Growth Product Manager for Loom

I love Loom, and Atlassian is a great place to grow your career. This one should definitely be on your radar.

→ Job description

4. Perplexity is hiring for a Growth Marketing Manager

Perplexity is on a tear, so this is guaranteed to be a great opportunity.

→ Job description

5. Strava is hiring for a Growth Marketing Manager, Retention

Run, don’t walk for this one. All fitness apps struggle with retention, so this is guaranteed to be a great learning experience.

→ Job description

6. Duolingo is hiring for a VP of Growth

Interestingly, this one is for VP of Growth and Product Marketing - an unusual combination, but still worth exploring.

→ Job description

7. AirBnB is hiring Sr. Growth Marketing Manager

Airbnb is a fascinating company and a masterclass in growth. If you want to specialize in marketplaces, this one is for you.

→ Job description

8. Ramp is hiring for Growth Product Manager, Website

This is a great transition role for growth marketers looking to move into product management. Website PMs are becoming increasingly popular, signaling that companies understand their website is a product and treat it accordingly.

→ Job description

And what’s the fastest way to land a bigger title? Getting a new job, of course. In your current role, getting a promotion requires earning it - proving yourself over time. But getting a promotion by switching jobs? All you have to do is sell yourself. And let’s be real: talking the talk is a lot easier than walking the walk.

As a result, people job-hop, chasing the biggest title they can get - often landing in leadership roles long before they’re ready. But the focus on rapid title inflation over true growth can leave careers as shaky as houses built on quicksand. Severe burnout and being fired are just some of the consequences of rushing through career stages without building the necessary skills and experience.

You know who faces a similar problem? Startups. If they fundraise and progress to the next stage too soon, it can be a near-death sentence. Unreasonable pressure, burnout, and down rounds often become harsh realities. And since we study and think about startups far more than our own careers, let’s draw some parallels.

Fundraising stages are like… career growth stages!?

Too meta? Hold on, just stay with me…

Startups grow through well-defined stages, each marked by specific milestones and challenges. These stages provide a clear structure for both the company and the market to evaluate progress and establish a predictable growth curve. Consider applying a similar framework for your career.

Titles, to some extent, can serve the same purpose. However, we often chase titles without fully understanding what needs to be accomplished at each stage of growth. Instead of focusing on meaningful milestones that signify true readiness, we blindly skip ahead. So, let’s compare and contrast the structured growth of startups with career progression.

Series A… is like an Individual Contributor role.

For a company: At this stage, the goal is to demonstrate Product-Market Fit (PMF). The company identifies a problem in the market and creates a solution that customers stick with. They start seeing early traction - acquiring customers, achieving good retention, and learning how to monetize. It’s about proving that there’s something valuable here while laying the groundwork for future growth.

For you: Just as startups strive to find PMF, you’re figuring out your skillset niche. What problems do companies have that you can solve? Whether it’s brand marketing, product management, data analytics, or another area, you need to identify your unique strengths and deliver results that your “audience” (your employer) values. Companies should want to retain you because your contributions are making a difference.

Series B… is like a Principal role.

For a company: At this stage, the focus shifts to scaling. Companies double down on what’s working, refine their processes, deepen expertise, and expand their reach while staying aligned with their original Product-Market Fit. It’s all about building on a solid foundation to grow sustainably.

For you: Similarly, this is where you begin building deep expertise and becoming a recognized authority in your field. You’re still working within your original “PMF” (your core skillset) but are now optimizing and scaling your impact. Like a Series B company refining its operations, you’re honing your craft to drive bigger, more meaningful results. Many at this stage see their titles upgraded to include "Principal" or "Architect," reflecting this deeper level of mastery and strategic influence.

Series C… is like a Manager role.

For a company: At this stage, diversification and optimization take center stage. Companies refine operations and expand into new initiatives, such as entering new markets, launching additional products, or exploring complementary revenue streams. The focus is on sustaining growth while maintaining efficiency.

For you: This is where you begin transitioning from being a strong individual contributor to managing others. Managing people requires a new skill set (aka, new initiatives!) - delegating work, mentoring team members, and ensuring the team’s collective success. At the same time, you continue leveraging your core expertise to drive results. Just as Series C companies often branch into adjacent markets or products, you may find yourself managing other departments or responsibilities beyond your original focus. It’s about scaling your impact through others while maintaining alignment with your strengths.

Some companies expand to Series D, E, F, and beyond… but let’s not get silly here.

IPO/Going Public… is like an executive role.

For a company: At this stage, the company is a market leader, with significant responsibilities to investors, employees, and the public. The focus shifts to maintaining growth, managing public scrutiny, and balancing the needs of stakeholders while staying competitive in the market.

For you: This is the "final boss level" - a leadership title. As an executive, you wield significant influence and carry immense responsibility. However, with greater scrutiny and organizational complexity, decisions become slower, stakes are higher, and trade-offs are unavoidable. Like a public company prioritizing long-term success over quick wins, your focus shifts from individual contributions to shaping strategy, fostering organizational health, and ensuring sustainable growth for the teams and systems you oversee.

What can we learn from fundraising stages that applies to our careers?

A lot, actually.

First, and foremost, don’t be in a hurry to get to the next ‘stage’:

Startups that raise prematurely often face unsustainable pressure, sometimes leading to failure. The same applies to your career. Jumping to a Principal, Manager, or Executive role before you’ve mastered the stage you are at can result in burnout or even being fired. Each stage must be completed fully and on the right terms to ensure success at the next level.

So in order to complete each stage properly, make sure to:

Know your Product-Market Fit (PMF):

In both startups and careers, your first task is finding *your* PMF: What problem are you solving, and what unique value do you offer? For your career, this means aligning your "product", or your superpowers, with market needs. Avoid "dead zones" like doing what you dislike (even if you’re good at it) or what you enjoy but aren’t skilled in. Long-term growth hinges on finding this sweet spot.

Define your Ideal Customer Profile (ICP):

Growth requires clarity about your "customer"- the company paying for your skills. Identify your career ICP: the industries, roles, or audiences that align best with your strengths. For instance, I focus on B2B SaaS, primarily in the productivity category for scaling businesses (Series B and above). Without this clarity, you risk restarting from scratch with each job change.

Evolution is essential:

Success is about thoughtful expansion. Just as companies expand their PMF or launch new products, you must evolve to stay competitive. Start with your core strengths and expand your skillset to meet changing market needs. Whether it’s learning new tools, taking on new roles, or broadening responsibilities, ensure every evolution aligns with your long-term career goals.

Choose your ‘investor’ carefully:

For startups, selecting the right lead investor is critical. For your career, this means choosing the right company and manager. A great manager and supportive environment can be transformative, while a poor match can stall your progress. Be strategic and intentional with these choices.

Don’t forget about your ‘angel investors’:

Startups often seek angel investors for strategic advice and mentorship. Similarly, you should cultivate relationships with mentors or advisors who can provide pointed guidance and help you navigate challenges. These "career angels" can be pivotal in guiding you through transitions or helping you avoid common pitfalls.

Not every company needs to go public, and not every career needs to end at the executive level:

Just as many small and medium-sized businesses (SMBs) thrive without ever going public, many individuals can build fulfilling, impactful careers without pursuing executive titles. A company doesn’t need to be on the stock market to be successful, and similarly, your career doesn’t need an executive title to be meaningful.

There’s immense value in being a high-performing individual contributor who loves their craft. Mastering a niche and delivering exceptional results can be just as rewarding as climbing the corporate ladder. Success isn’t about following a one-size-fits-all path - it’s about finding what works best for you and thriving within it.

By applying these principles, you can build a sustainable, impactful career - just like a well-run startup thrives through thoughtful growth.

Don’t be a generalist:

Over-diversification can dilute your impact. Startups that try to tackle too many markets or launch too many products too soon often lose focus and fail to excel in any one area. The same applies to your career. Specialization often creates differentiation - it’s what makes you stand out.

Focus on mastering your core strengths first and building a solid foundation. Only expand your skills or take on new roles once you’ve achieved depth in your niche. Strategic growth, rather than trying to do it all at once, ensures you remain impactful and in demand.

Final Thoughts: Choose Your Own Adventure

Understanding the parallels between startup growth and career development can be a game-changer. It helps you see patterns, avoid common mistakes, and identify opportunities for growth. Just as startups leverage strategies tailored to their stage, you can adopt a similar mindset to chart your career path. The ultimate goal? To build a fulfilling career that aligns with your strengths, passions, and goals.

Would you like to sponsor my newsletter? Click here.

Edited with the help of Jonathan Yagel.

If any of the links don’t work, it means the company has taken the job down.

1. Growth PM, ChatGPT @ OpenAI

→ LINK

2. Growth PM @ Perplexity

→ LINK

3. VP, Growth Marketing & Demand Gen @ Gong

→ LINK

4. Group PM, Growth Lifecycle @ Netflix

→ LINK

5. Growth PM @ Amplitude

→ LINK

6. Sr. Growth PM @ Hubspot

→ LINK

7. Partner 22, Performance Marketing @ Andreessen Horowitz

→ LINK

8. Growth Marketing Manager @ Roblox

→ LINK

(I want some robux for my son, pretty please.)

9. VP, Growth Marketing @ Upwork

→ LINK

P.S. And be sure to check out Ben’s Next Play Substack—they consistently highlight startups that are hiring, showcase hot jobs on the market, and even organize events to bring people together.

next play

We help people find their next play by sending opportunities, hosting gatherings, and curating content.

By Ben Lang

Would you like to sponsor my newsletter? Send an inquiry.

Edited with the help of Jonathan Yagel, Assistant to the Regional Memeger.

Unlock Your $1,500 Offer

How many times have you walked into an annual performance review, hoping… no, expecting a promotion or raise… because you’ve crushed your work and surely your manager will recognize it. Right? And how many times have you walked out with only disappointment? Unfortunately, it happens all the time. You are not alone. And then resentment, anger, and quiet quitting follows. You may even switch jobs, hoping to be *seen* somewhere else. But history is bound to repeat itself, unless you take control of your career. 

This post is about how you should do it.

Your Career, Your Responsibility

Here’s something I wished I’d learned a lot earlier: Growing your career is your responsibility—not your manager’s. If you’re sitting quietly, hoping they’ll magically notice your aspirations and reward you accordingly, you’re putting your chips on the wrong hand.

The reality is that your manager isn’t incentivized to proactively grow your career. If you just keep hitting goals and exceeding expectations, and not saying anything about your aspirations… most managers assume you’re happy where you are and won’t take any action. They need someone to do the work and you are perfect at it! Why change anything?

I experienced it firsthand the first time I planned to rage-quit because I didn’t get the expected promotion from IC to Manager. I sat quietly through my performance review, stewing inside. My manager had nothing but positive feedback, yet there was no promotion in sight. WTF.

Frustrated, I began responding to recruiters and got myself a manager-level offer. "There," I thought, "that’ll show them." To my surprise, my attempt to quit was met with, "What on earth are you doing?" Not the response I anticipated.

My manager asked me to take a walk around the office. During the walk, he asked why I had never shared my aspirations to become a manager. I was taken aback—why would I need to tell him? Shouldn’t he just know?

“No,” he explained, “not everyone wants to be a manager. But now that I know, I’ll fast-track you. Give me a few months—You’re ready.”

I felt stupid. Why hadn’t I told him? Why did I just expect him to know? He’s not a mind reader, after all.

That one conversation changed my entire outlook on how I would manage and grow my career. 

And it all starts by having conversations now—before performance reviews, compensation decisions, and team calibrations are locked in stone.

Level 1: Awareness - Align on Expectations Early

If you want to change the trajectory of your career, you need to get on the same page as your manager. That means—at the very least—clearly communicating what you want and are looking for.

Want a promotion? More responsibility? To stay the course? You have to tell them. Don’t assume your manager knows where you want to end up. They’re juggling multiple priorities and probably aren’t spending time trying to anticipate what you want.

Here’s your first move: Schedule time to discuss your career. Even just a simple request like, “Hey, can we carve out time next week to discuss how I’m doing and where I want to grow, professionally?” gives your manager time to prepare and shows you’re serious.

The goal of this meeting? To make them aware of your goals. If you are looking to climb corporate ladder, they should know. If you want to grow specific skills, tell them. If you are craving more responsibility, ask for it.

Pro Tip: Don’t surprise your manager with a sudden career conversation. Give them a heads-up: “Next week, can we talk about how I’m doing and where I’d like to grow?” This shows respect for their time and allows them to prepare thoughtful feedback.

Level 2: Clarity - Ask What “Great” Looks Like

So, how do you get guidance on what it takes to reach that next level?

I can tell you one way that WON’T work: Going to your boss with “I want a promotion—what do I need to do, to get promoted?”. Because they don’t know you that well, there’s a high chance they’ll give you a generic answer, like: “You need stronger communication skills. That is not actionable or helpful. You even might put in the work and practice the things you think will make a difference—only for them to later say, “Oh, but you also need better presentation skills.” 

Frustrating… but also easily avoidable.

Instead, be more proactive in this process. Ask them to describe the most important skills of people who are already at the level you aspire to.

To get more specifics, ask questions like:

• Can you give me examples of what strong communication looks like at the next level?

• Can you let me know the next time you see someone demonstrate it?

• Can you point out next time I could have done better with my communication? Or when I showed what you are looking for?

Once you have those examples, compare and contrast them with your current communication skills to identify gaps. Then, discuss those gaps with your manager and share the steps you’re already taking to improve, asking if there is anything they’d add to it.

Pro Tip: Recruit your manager to help you. Frame the conversation like this: “Will you help me get there?” This turns your manager into a coach and ally. Instead of the judge on the sidelines, they become someone invested in your success.

Level 3: Consistency - Check In Regularly

One conversation won’t cut it. Career growth requires ongoing alignment. If you wait until the end of the year to discuss your performance, it’s already too late. Decisions about promotions and raises happen well before the final review (Meaning: They are being discussed *right now* for January/February cycles).

Make career check-ins a regular part of your 1:1s on a quarterly or bi-annual basis. These aren’t moments for ultimatums or demands—they’re alignment exercises. Does your manager see your progress? Do they understand your goals?

If you sense any disconnect, course-correct early. Regular feedback loops ensure you’re never surprised by the outcome of a review.

What to do if your manager won’t engage?

There are a lot of shitty managers out there. The sad reality is… this:

Not every manager is great at career coaching. Some may lack the skills, interest, or maturity to have these discussions. If your manager refuses to engage with you when you reach out about these kinds of things, take it as a signal.

You have really one of two options:

1. Accept It: If you like the job or simply need it for now, adjust your expectations. It’s better to have clarity than to face constant disappointment from unrealistic expectations.

2. Find Another Manager: Look for opportunities elsewhere in the company or even at a different company.

Having these conversations—even if they don’t go well—gives you valuable data about your career trajectory.

Get Started… Today.

Performance reviews are not the time to drop surprises. They’re the culmination of ongoing dialogue. The good news? Right now is the right time to get started.

Here’s what to do today:

• Schedule a conversation with your manager over the next 2 weeks.

• Share your goals and aspirations.

• Ask about what “great” looks like at the next level.

• Do self-evaluation about your delta to that ‘great.’

• Talk to your manager about what your delta is and how you will work on it.

• Commit to regular check-ins.

Don’t leave your career to chance. Managing your growth isn’t just about doing good work—it’s about making sure the right people know what you want and how they can help you get there.

P.S. And don’t do it alone! Find your circle of support - Sidebar can help.

Would you like to sponsor my newsletter? Send an inquiry.

Edited with the help of Jonathan Yagel.

This post brought to you by HubSpot: Driving product adoption and retention just got easier. Now, marketers can use key product signals for personalized lead nurturing, pass qualified leads to Sales, and re-ignite at-risk customers. Try the improved Amplitude app for HubSpot.

Check it out

People ask: “How do I build my personal brand? How do I gain followers fast? What should I post to get the most likes? How do I go viral? How long will it take?” Somehow, the message has landed that building a personal brand will lead to more opportunities, higher pay, and greater attention.

But here’s a hard truth: trying to build your personal brand early in your career is pointless. Instead, focus on doing the best work of your life, and your brand will follow. If this seems counterintuitive, it’s because there’s a loud army of “influencers” highly incentivized to sell you their brand-building courses—complete with “grow your LinkedIn following” tips, “build your personal brand” tricks, and algorithm hacks.

You should opt out of all that.

(Unless you want to be a instagram/tiktok social influencer, I guess? But this post is for people who work in corporate world and not looking to become instagram models.)

Because the best way to develop a personal brand is to do exceptional work, deliver results, and provide real value. Credibility and trust come from your contributions and achievements, and that’s what lays the groundwork for a strong personal brand. When people talk about what you’ve accomplished, your personal brand will grow organically. Chase the brand first, and you’re putting the cart before the horse.

Personal brand is a lagging indicator.

Your personal brand is a lagging indicator of you doing great, meaningful work.

Another way to look at this is to compare personal brand efforts to any given company’s brand work. Andrew Chen wrote an amazing post about branding for early-stage startups:

“Brand marketing is mostly useless. Startups build a great brand by being successful, finding product market fit and scaling traction, etc.

If this seems contrarian to you, it’s because there’s a vast ecosystem of consultants, agencies, and other middlemen who are highly incentivized to have you spend $ and effort on non-ROI/non-performant activities. Early startups should opt out of all of this.

It’s easy to confuse correlation and causation: If you’re starting a consumer startup, you see successful late stage cos with fawning media coverage, amazing conference speaking slots, celebrities on the cap table, etc., and think that’s what caused their success: Great brand.

But a great brand is the lagging indicator of success. The buzz is created by the hard work that the entrepreneurs put in: Finding product/market fit, hiring a great core team, finding acquisition channels that scale. Brand marketing is great, but it should be layered on later.”

The same goes for you and your brand. Chasing a reputation before building real expertise is like a startup trying to scale a massive brand without a solid product. Don’t get fooled by the Justin Welshs of the world, selling the dream of monetizing your LinkedIn audience—it’s borderline a marketing pyramid scheme. Don’t get blinded by ‘viral’ posts and endless selfies. Just don’t do it. 

Focus on doing the work, first. Focus on substance over flash.

“Wait, but Elena… YOU have a personal brand!?”

Does it feel a bit odd hearing this hot take from me? It might look like I’ve intentionally ‘built’ my brand. But honestly, that’s never been the goal—even today.

Sure, I’ve invested in public speaking, posting on LinkedIn, this newsletter, and creating courses for Reforge—but that came later in my career and alongside meaningful operator work that I was actively engaged in.

And my primary aim was always to democratize knowledge. If more people shared insights openly, think of all the mistakes we could all avoid. Plus, creating content helped me attract a more qualified pipeline for my advising work, so I could find better-fit companies to collaborate with. 

It was always about impact and effectiveness, not personal brand building. My ‘brand’ was an unintentional output, but never a desired destination (even to this date).

Personal Branding ≠ Content Creation

While I frown upon personal brand building, I do encourage people to share content from the insights they’ve collected. I hesitate to even use the term ‘content creation’ because it’s become associated with content marketing teams churning out meaningless vanilla blogs (more like blah-gs, right?). But creating really good content is a valuable thing. 

I genuinely believe everyone should share their learnings more publicly to democratize information. If the tech industry were more willing to share our insights, we’d all be so much farther ahead. We all have lessons and stories worth sharing, and by doing so, we’d help others avoid the same pitfalls.

Many people fear that sharing their knowledge makes them less marketable, like they’re giving away their value for free. But that couldn’t be further from the truth. Frameworks and examples are just data points. The real value lies in how you operationalize those frameworks and execute those examples—that’s where your marketable skills shine.

Story time: How I did it.

My journey into sharing knowledge began with public speaking. And let me tell you… it was rough. I got invited to speak at a BI conference, chose a topic that was way too specific, talked too fast, got way too in the weeds, and ended up with just three people in the audience—none of whom had any questions afterward. I left feeling defeated and convinced I’d never put myself through that again.

It took me a full year to recover from that “trauma” before attempting public speaking again. This time, I knew I needed a better plan. So, I reached out to my company’s events team, who were always on the lookout to sponsor conferences or, even better, find opportunities for internal speakers to deliver keynotes. Sometimes, all it takes is raising your hand!

My big break was a unique situation—I met Brian Balfour at Reforge. This was the real turning point for me, and was the first step-function change: He put me in front of relevant audiences. This allowed me to find the people who actually were interested in what I had to say! Plus, Brian straight up told me: ‘Don’t just talk about one dashboard for your keynote. That is boring. You need to give people the right context, tell them a story, and help them see why it matters to them.’

Getting to create courses for Reforge was an amazing feedback loop. It showed me what people found valuable and what they needed to learn. This was my Product-Market Fit moment. 

And the interesting thing is… if I’d wanted a more traditional career, I might have just kept all of my content within the Reforge system. They’re amazing. The only reason that I set out on my own was when I decided that I wanted to explore solopreneurship. Again, this wasn’t out of the interest of ‘building a brand,’ but to diversify my acquisition channels for my solopreneurship business. I initially started with LinkedIn to increase my reach, but I later added Substack to have ownership of my audience. LinkedIn’s algorithm can boost visibility, but it can also take it away, leaving me with little control.

So, again: The choice to spend more time creating content and posting more than just the occasional insight was directly related to my decision to leave full-time roles.

This is also related to how much ‘market demand’ I was experiencing. After a certain amount of time, people were asking me to post more! I felt a ‘pull’ to post more and could tell that what I was sharing was helping. My whole progression was an evolution: I found the right people and could tell that what I was sharing was valuable, so I kept sharing more. 

Side note: The memes.

If I do have a brand, I would say my memes are a big part of it. Was that some sort of clever strategy to craft a unique brand for myself?

No. I just like memes 😂. Check out my 10 funnies memes here.

But I will say: I love that they are disarming. If you have to hit someone with a hard truth, humor is a great way to do it. People can see the truth, without getting defensive. A picture is worth a thousand words, right? Adam Grant said it best:

Final thought: It’s not about you.

If I can sum all of this up, I’d put it this way: Don’t make it about you. So much of our society is about making yourself look good and getting the maximum amount of attention. Yet ironically, the people who I’ve seen be the most successful with building an audience are the ones who are least concerned about their own fame. 

So instead of worrying about how you’re perceived, focus on sharing what you know. Whether that’s through writing, speaking, or mentoring, giving away your knowledge helps you become recognized as a thought leader. When you consistently contribute to your community, your brand builds itself. People start associating you with expertise and generosity, rather than a manufactured image.

By shifting the focus from building a personal brand to building real expertise and sharing value, you’ll not only grow faster, but you’ll also develop a reputation that’s based on substance, not style. So, stop worrying about your brand and start focusing on doing great work—your brand will take care of itself.

Would you like to sponsor my newsletter? Send an inquiry.

Edited with the help of Jonathan Yagel, Assistant to the Regional Memeger.

Apply Now

I hate work-life balance.

Or, more specifically, I hate that term. It sets you up for failure by implying there's some magical balance or a 50-50 split between your personal and professional life. That’s just not realistic. Nobody has it. Nor is it actually desired.

Instead, I’d like to think about this as work-life prioritization: some days or weeks or even months or years, work takes the front seat. At other times, personal life and family takes priority. Trying to force a consistent, equal ‘balance’ creates unnecessary stress and guilt because the reality is that life’s priorities are always shifting.

The key is to focus on prioritizing what matters most at any given time.

Some days it’s, “I’m prioritizing my family today—my kid is sick, and work is just going to have to wait. There’s no work-life balance today. There’s only the family priority at this moment.” Some other day, you may have a high-stakes presentation at work that requires all of your time and energy. You can’t aim for perfect balance every day, but you can aim for a balance over time that works for you.

Thinking in terms of prioritization instead of balance helps you set more achievable targets and, frankly, be truthful with yourself, so you’re not constantly feeling guilty. The goal is to make these prioritization decisions weekly, daily, and sometimes even hourly, depending on the situation around you.

The Menu of Boundaries

If you’re reading this post, you do need help figuring out how to prioritize your personal life better. So many of us struggle with the question: How do you create space for your personal priorities? Especially if you work in tech, there’s always more to do. If you’re at a startup, it’s even worse. People need you! Things are constantly falling apart… The company depends on you! Not to mention, they’re the ones paying your paycheck. There’s always a sense of urgency, and someone always needs something.

If you don’t proactively create boundaries, work will take over your life because work is always going to demand more from you. It’s easy to push your family or personal life aside because work is right there in front of you, asking for your attention all the time. And then comes the guilt of not having any time for yourself, missing important moments with your kids, or damaging relationships.

My approach to this? I think about it like a menu of items you can choose from to create boundaries. You don’t need to do every single thing on the menu—actually, you can’t. But you should go through and choose what’s right for you. Depending on where you are in life, you might need more space for your personal life, you might need less. For instance: People with kids will most likely need to “order” from the menu more. If you don’t have kids, maybe you’ll want to “order” less to hit your career goals.

Either way, here’s what’s on the menu:

Option #1: Set Working Hours: Decide when you’re unavailable. It might be 5pm, 6 pm, 7pm, later. It doesn’t mean you’ll never go past those hours, but 90% of the time, stick to it and communicate to your team that you’re unavailable outside those hours.
For example, I have children, so I have to draw a hard line. I tell my team, “I’m a mom from 6 to 8pm every day and it’s non-negotiable. My calendar is blocked and I’m unavailable.” After 8pm, I’m done. My brain doesn’t function well at night, but I’ll be up and ready at 6am if needed. But that time with my kids is precious and non-negotiable.

I’ve even had CEOs request meetings past my working hours, and 9 out of 10 times, I say no. I’m polite, but firm: That’s my family time. It’s really hard to maintain that boundary because I worry people will think less of me or not include me next time. But honestly, I’ve gained more respect by holding that boundary.

Option #2: Gym time: Another big one for me is gym time. People, especially in tech, tend to sacrifice their physical health for work. But protecting that habit is one of the best things you can do for yourself (and your mental health). I go to the gym every day for an hour. That time is also non-negotiable.

My team knows, and my calendar reflects it. I’m not available during that time because that’s how I recharge and stay sane. Yes, I skip it every now and then, but it’s rare. Studies show how important physical exercise is for reducing stress and improving productivity, so it’s an investment in your ability to function at work.

Option #3: Lunch breaks: So, this is actually one I don’t do. Some people really value taking this time in the middle of their day, but I’m terrible at this: I always eat at my desk. But I’ve seen others strictly protect their lunch break, and they say it works well for them because it gives them a chance to disconnect and come back refreshed, as opposed to working 9 straight hours and burning out completely. If you work from home, this can be some key time to yourself. And this can be a great move if it allows you to reset and avoid reaching the end of your day feeling completely brain-dead.

Option #4: Travel expectations: This one is especially relevant if you’re in a remote role with frequent travel. When I first started at Dropbox, I was traveling a lot: like, 6 weeks out of my first two months. It was totally unsustainable. Fortunately, I was able to set a boundary: no more than two travel weeks per quarter. And they can’t be back-to-back, since that completely removes my ability to recover and reset with my family. 

I will say: This is something that I confirmed when negotiating my full-time role, and this may be harder to establish, once you’re already in a role. But I don’t know if enough people realize they can negotiate this.

Option #5: Pick-up/drop-off times: Another one I see a lot is scheduling blocks to do school transport for kids. In general: It seems like men are fantastic at protecting this time. They just say, “I’m picking up my kids, and that’s my time.” Women? We’re terrible at it. We feel like we don’t have the right to block that time, but these moments can be precious. 

Option #6: Pick your own: If an idea came to mind as you read this list, go for it! Although you can use my suggestions, the real goal is to find things that are important to you and protect them. That will be easier to do, if it’s something you deeply care about or it’s something that really helps you to recharge.

Accepting the Tradeoffs

It’s important to acknowledge that work-life prioritization looks different at various stages of your career. Early on, it’s common to prioritize work over everything else. I did this myself. I was consumed by my work because I loved it. It was my whole world, and it accelerated my professional growth. You do have to recognize the trade-offs: if you start prioritizing your personal life, whether it’s because of kids, hobbies, or just a desire for more balance, your career will have to adjust. Not necessarily slow down per se, but you will have to ruthlessly prioritize what you do at work to achieve the same results, because you’ll have less time—and that’s okay. It’s about making a conscious decision.

But even if you are super career-focused, there are reasons to prioritize things outside of work: I already mentioned the value of physical fitness in terms of improving your focus and longevity. A broad range of interests also allows you to work harder, for longer.

For instance, I’ve seen a lot of colleagues end up in a kind of mid-career slump: As people hit the 15-year mark or so, we often start losing relevance to newer technology or younger colleagues. If your whole identity is based on being good at your job, this can be devastating. So even if you don’t have other reasons, try investing in personal hobbies, whether it’s coaching a little league team, crocheting, or raising chickens (like me!). You need something that pulls you away from work and helps you have an identity outside of your professional role.

Setting Boundaries Is Possible for Everyone

You really can do this. I understand that, as a VP, I have a lot more control over my schedule… but it’s absolutely not true that these kinds of boundaries are only for executives or senior leaders. In fact, many people in these senior positions are even worse about setting boundaries because they feel a greater degree of responsibility for their company or colleagues. Even early in your career, you can ask for what you need. You may not always get everything, but you’ll never know if you don’t ask. 

I clearly remember the first time I asked to leave work early because my baby was sick. I was terrified. I thought I might get fired (silly, I know). Instead, my boss was so supportive! That experience taught me that I had more control over my schedule than I realized. 

Of course, you need to build relational equity first. Show that you can perform, gain trust, and then use that trust to negotiate the work-life prioritization that fits your needs. Sometimes, it’s as simple as having a conversation with your manager about expectations. And remember, the longer you stay with a company and prove your value, the more flexibility you can negotiate over time.

Final Thoughts

Work-life prioritization isn’t about finding a perfect balance. It’s about making conscious decisions based on the realities of your life at any given moment. Start with small steps—pick one or two areas where you can create space for yourself and protect it. Over time, you’ll find that this approach makes you more effective at work, more present at home, and ultimately more fulfilled in both areas.

Edited with the help of Jonathan Yagel—check out his awesome Substack.

Apply Now

I have a confession to make: I was a shitty manager. 

I still remember it so clearly—I got promoted to a managerial role young, in my early 20s, as I was eager to climb the corporate ladder. I was excited about my career progression, but I also wanted to rebel against all things corporate: no work-about-work, no 1:1s, no check-ins. 'Come on, team! We’re going to do the best work of our lives! No meetings!' I figured we could line up a queue of work and just take it on.

The sad thing? I actually thought it was going great. Until one of my guys pulled me aside and asked: “How do I grow in my career, if we never have an opportunity to have 1:1s?”

That was like a slap in the face—here I was expecting that kind of guidance out of my manager yet not comprehending that I needed to give it to my team, too. Even if not all of the 1:1s I was having with my manager were that helpful, it was still a chance to manage up. But I wasn’t offering even that to my own team...

As I looked more closely, I also saw that my small team had started to drift apart and was starting to work in silos. So, wait… maybe we do need team meetings!? I found that some rituals are there for a reason. I do think my intentions were good: I just wanted to get shit done!

But even that was the least of m problems… I had incredibly hard time letting go of my IC work. Even at the Director level, I was still doing IC work: Filing Jira tickets, writing PRDs, writing SQL. As I’ve shared before, at one point, my amazing manager gave me an ultimatum: 

‘If you want the next promotion, you need to stop doing so much of the work yourself. Your job is to lead, not do all of the individual contributor stuff. For the next 6 months, I’m going to review the logs… I want to be sure that you have not accessed the database, filed a Jira ticket, or created a PRD, yourself. You have to learn to delegate. You have to enable your team to do it. If you can do that, the next promotion is yours.’

Those 6 months were treacherous. Things I knew I could do in 3 minutes, would take me an hour to train, explain, and validate with someone else. But I’m grateful that happened because it ripped the bandaid off and I finally learned that doing it yourself is not the way to scale a team. 

All of this was a decade and a half ago, and I’ll admit that I got better at it: Mainly because I had fantastic managers and finally learned to love mentoring people and helping them grow (instead of loving doing individual contributor, or IC, work myself). After that (emotional) slap in the face from my first report, I’ve seen so many times how guidance from a manager can shape a career and unlock potential. And I experience so much satisfaction in seeing someone who worked under me grow into larger, more impactful roles. That’s what I cling onto, to justify all of the pain of being a people manager. 

Because, make no mistake, management roles come with a lot of pain. And I wouldn’t wish a manager role on my worst enemy.

Falling into the management trap

Unfortunately, many people see management as an inevitable part of a successful career. But as I learned the painful way, management is not just a title. It’s a skill—and not a particularly easy one. It’s definitely not everyone’s superpower. To make matters worse: the people who really want to be managers often shouldn’t be.

One of the major issues is that talent in your IC role has *no* correlation with talent as a manager. You’re a great data analyst? Amazing. Legendary designer? Beautiful. Top-tier dev? Fantastic. None of those have anything to do with what makes you a good manager. 

Personally, if you don’t enjoy mentoring or solving people issues, I’m guessing you’ll find management to be a horrible job. Because that’s one of the things they don’t tell you: 70% (or more) of management is managing people problems, with 10% of your time being spent on every direct report you have. As one of my mentors once told me as he was scaling his team: “More people, more problems.” That’s exactly how I see it. Yes, you get to make those glorious leadership-level decisions and that fancy title, but most of the job is people issues & repeating strategy like a parrot. And don’t get me started that you have to absorb all of the blame if *anything* goes wrong (even if it’s not technically your fault).

I do understand why people want to take manager path: The title, the money, the prestige. But there’s a dark side to it.

A different path: The Principal or Staff IC

So, what if you could keep doing the work you love, never have to manage people… and still advance in your career? I’m talking top-tier pay, prestige, and autonomy.

Is this a dream? Nope, it’s the ‘Principal’ IC path.

Fortunately, this is becoming more and more common: At Dropbox, we’ve recently hired a number of these types of roles, see example of the Staff PM here:

Staff (or Principle) Product Managers, Designers, Engineers and Architects (which are all IC roles)... are getting paid the same amount a Directors, or even VPs!

Examples of cash comps, which don’t even include bonus or equity:

• Staff Product Manager - Up to $271K USD salary!

• Staff Data Scientist - Up to $256k salary!

• Staff Payment Specialist - Up to $243k salary!

(Note: One area I’m not seeing principal roles? Marketing. Maybe that will come at some point, but my hunch is that marketing has so many different specializations and sub-functions, which means senior marketers will almost always be required to manage other marketers.)

For anyone who doesn’t want to be a manager, this is a great path. It wasn’t that common 10 years ago and many people still aren’t aware it’s an option, so they don’t even consider it. But now that this is a possibility, I think it could completely change the game. If you can make the same salary on either path, there’s no longer a direct incentive to jump (or fall) into the management track.

This lets every employee play into their superpowers, which is good for them and good for their companies.

Another different path: Advising

What about if you are already in a traditional leadership or management role… but hate it? 

Well, as you already know, this is what happened to me. And I wholeheartedly encourage you to try out advising! 

I do need to be clear, here: Advising is not a good option if you’re not already in a leadership role. If you’re early in your career, put in the time to hone your craft and build your skillset. Over time, your abilities as a senior-level Principal IC will be in high demand and you can explore this route, but don’t try to skip the initial steps.

But if you do find yourself feeling trapped on the upper end of the corporate ladder, I’d encourage you to consider it. I found this to be another great way to escape the traditional framework, as I got a chance to be involved in the most important strategic projects for excellent companies, retained autonomy, and got paid well… all without needing to manage a team.

Conclusion: Why now?

Okay, so, what changed? Why are these new types of roles popping up?

I see a number of reasons:
(1) Companies are finally recognizing the problems of the old approach. The issue isn’t just that the system has been creating horrible managers. It’s even worse than that! There are so so many stories of an incredible IC who’s pushing the company forward in all the right ways, so they get promoted into management. It turns out they hate management—or just weren’t prepared for it—so they don’t do well at it. They become an underperforming employee and the company has to part ways with them. Talk about shooting yourself in the foot.

(2) Employees have a larger voice, now. As younger generations are entering the workforce, they’ve been better at articulating their needs. Millennials have done this better than GenXers, and Gen Z does it even more. Just recently, I’ve had multiple conversations with my team where people expressed their disinterest in managerial roles and their desire to pursue principal roles. I couldn’t be more proud of them for knowing what they want, and I support them to the moon and back.

(3) Improved collaboration tools and technology. There has been so much investment in project management and communications platforms over the last 10-15 years, which means less need for managers and more ability for strong ICs to manage themselves.

(4) The secret is out. With places like Linkedin and other public forums where people can share more details about their work life, more people are realizing… just how shitty most of the management jobs actually are. Insane stress, heart attacks, quality of life. People are starting to ask, “Wait, why would I want that?” These kinds of spaces show what has always been behind a curtain of sorts: the reality of life in management hasn’t always been readily available, so most people just saw the perks.

For all of these reasons and probably some more (AI, right?), we’re seeing a new range of possibilities for people to get many of the perks of leadership without forcing people into management. 

Whatever path you take, I wish you all the best!

P.S. And don’t miss Leah Tharin’s post on this topic as well:

Leah’s ProducTea

Normalize Individual contributor Leadership

The unhealthy obsession with manager-centric leadership roles…

Read more

3 years ago · 33 likes · 6 comments · Leah Tharin and Elena Verna

Edited with the help of Jonathan Yagel—check out his awesome Substack.

Enter the hero of this story: the interim leader. Just like those 30-day free trials that somehow turn into lifelong subscriptions, interim leaders are here to save the day with a no-commitment, full-commitment kind of deal. 

What is an interim leadership? I’ve held interim head of marketing or growth roles at Miro, Netlify, Amplitude, and Dropbox, and my take is that Interim is defined as a full-time leadership role on a short-term, contractual basis (not to be confused with Fractional, which is a part-time, long-term contract). Details are as follows:

• The contract is usually <12 months with a flexible two-way termination clause

• There is a well-defined problem that the interim leader can come in and begin solving

• Available to start on short notice

• Some are open to full-time conversions, but if not, they will help backfill themselves

• They can be set up as a contract or full-time employee in your systems

• They are usually paid in both cash and equity (equity with no cliff, quarterly vests)

• They are not cheap—prepare to pay more than you would for a regular, full-time role

• For more details, check out my ‘Unpacking what it means to be an interim leader’ post

Why do people make a choice to start interim’ing? To give themselves more work flexibility, to recover from burnout, to double down in their specialization, or simply to try before they buy into their own next full-time gig (especially if they’ve been burned by a bad transitional hiring process). I shared my reasons in this post.

But there is SO much benefit for companies, too!

Here are 5 reasons (plus a bonus!) why more companies should embrace this ‘try before you buy’ approach.

1. Immediate Expertise

Finding a leader is usually a 6–12 month ordeal. But what if you cannot wait? Interim leaders can (usually) start on Monday and plug in right away. 

2. Reduced Risk 

The negative impact of a failed leadership hire is… crushing. It sets your business back, causes a wave of internal disruption, and leaves long-lasting scars that take years to heal. So if you have any uncertainty about the candidate or the type of expertise you need, de-risk it by getting them as an interim, first. If things work out, many interims are open to full-time commitment. And if not, there is less disruption to everyone because there was a common understanding that it would be a short term engagement from the start.

3. Right Leader at the Right Time

As businesses rapidly shift (going through hypergrowth, digital transformation, mergers, etc.), different people naturally fit better during different periods of the company. And while there are some unicorns who can mold themselves into whichever leader you need them to be, most people have superpowers that align with certain problems. If you're going through a lot of change, interim leadership is perfect because it's like ordering leadership à la carte: you get exactly what you need, seasoned to perfection, for a specific period of time, without any long-term commitment.

4. Disrupting the Status Quo

Interim leaders often come in with a mandate to shake things up. Since they are not looking for promotions or bigger scope, they come bullshit and politics-free. Their fresh perspective and lack of agenda can spark innovation and push the company out of its comfort zone. 

5. They help you hire the right person

If your interim leader is open to converting to a full-time role, great. But even if they're not, they'll help you hire the *best* candidate. There's nothing more powerful than hiring a backfill for... yourself. Interim leaders are subject matter experts in their field and have all the internal context, so they're perfectly positioned to hire a long-term leader—better than you could ever do.

Bonus! Promote via Interim

Do you have a leadership departure and aren't quite sure if any internal candidates are ready for the job? Consider giving it to them on an interim basis while you do your new leadership search. This allows you to see if your internal talent can stretch to fill the role, and if not, they can gracefully step back into their previous position without any awkwardness.

Are there any drawbacks?

One common push-back businesses have about hiring interim leaders is companies’ desire for a long-term commitment. But long-term commitment only happens when there’s a good fit. And if you think you can find that good fit by talking to a person for a few hours on Zoom, you are sadly mistaken. And the data doesn’t lie: most execs have an average tenure of less than two years. So look at the interim leadership as a way to get to a long-term, successful fit.

Other companies are concerned about the fact that the presence of an interim leader might create uncertainty or instability within a team, especially if employees are unsure about the future leadership structure. This can affect morale and productivity, sure. But what causes an even bigger disruption? A bad full-time hire. So pick your battles :)

My dream!

My dream is to normalize interim leadership roles. Whether it's a 'try before you buy' scenario or a short-term arrangement, it benefits both people and companies.

So, stop settling for the uncertainty of a full-time gig and explore the benefits of interim roles instead. It's like renting a convertible for a weekend road trip—maybe a bit pricey, but readily available, perfect for your needs, and if things go well, you might decide to keep the keys. So, buckle up and enjoy the ride.

Edited with the help of Jonathan Yagel—check out his awesome Substack.

Apply Now

I didn’t start my career in Growth.

In fact, I never expected to be in Growth at all—because this field didn't even exist when I started working. Yet, here I am, and I wouldn't have it any other way. How did I get here? For all of you who are still figuring out your career path, this story is for you. 

I graduated college with a degree in statistics. Like most of my classmates with that major, I planned to be an actuary. An actuary is that person who figures out your insurance rate. I know—riveting. I didn’t know anything about the corporate world, but thanks to my mom, I landed an internship in the marketing analytics department of a large grocery chain (Safeway). My big project was developing algorithms for personalized coupons based on customer shopping habits, in an attempt to increase shoppers share-of-wallet. I found the work really interesting, but the slow pace of a large enterprise drove me insane. After 12 short months, I set out to find something else. 

Where did you look for jobs in the early 2000s? Craigslist, of course. Which is where I found a data analyst job posting from SurveyMonkey (back then <20 people large). I didn't know much about the tech industry but the promise of a scrappy, fast-paced environment, all while being surrounded by extremely smart people sounded promising. Getting into tech was not easy—the hiring process at SurveyMonkey took over six months as they were interviewing many candidates, and I only got an offer when I received another offer and ‘threatened’ to leave the hiring process. 

The offer was a step back from my previous position, both in title and salary. It was a hard decision: I was only making $50K/year and every dollar was a big deal. But despite my rational objections, my gut kept telling me to take a leap. I felt that this was THE place for me. A huge selling point was the fact that I was their first analyst hire, which gave me a blue-sky horizon to do whatever I wanted. However, I still remember my ex-manager talking down about SurveyMonkey as I gave the notice: “Why are you going to some tiny, nothing company? What a mistake,” she said. I’m glad I proved her wrong :)

SurveyMonkey not only lived up to my expectations, but delivered something that in retrospect is very unique. It became a place where I truly built my career. The culture was a perfect fit for me: no bullshit, data-driven, with high velocity. The bar was high and I loved constantly having to reach for it. Plus, I loved the team around me—they were supportive yet highly demanding. I invested all I had into the data career track and became a director within five years.

Despite my love for data, I was always extremely passionate about the product. For example, I was creating a new SurveyMonkey account every week to go through every possible user flow to help me generate ideas for analysis and product improvements. I never ended an analysis on the data—it always came with a slew of recommendations on how to make a product better, and even included my janky design mocks (made them Excel back then!) to PMs’ and Designers’ distaste. Fun fact: Me living in the product always led to finding a ton of bugs. I remember our senior billing engineer telling me he dreaded hearing my footsteps in the hallways, as he knew I was coming to tell him about yet another bug he had to urgently file and hotfix. But most importantly, this habit allowed me to be a deep expert in our product, knowing where anything and everything was. It became a superpower in the next steps of my journey. 

I loved my impact as a Director of Data, although management was really hard for me—I had a hard time letting go of my IC work. My manager back then had to give me an ultimatum: I had to learn to delegate by not filing a single Jira ticket or writing SQL query for 6 months. If I did that… the next promotion would be mine. That was one of the hardest tasks for me—I had the constant urge to just quickly do it myself vs. taking time to get someone else to do it. But she was right in making me do this and after 6 months of agony, my team and I came out stronger on the other side. 

By this point, I had my eyesight on VP title—to continue growing my impact and maintaining my velocity of learning. But since VP of Data or Chief Data Officer roles were uncommon back then (and frankly not needed in the company at that time), I kept asking for more responsibilities—even outside analytics.

Eventually, I was offered the chance to start a product marketing team from scratch. I had no idea what PMM was, but figured I’d give it a shot and eagerly accepted. I hired a content manager and product marketer under me and dug in. But after less than a year, I realized that I was a fish out of water. The product marketer that I hired was so much better at that function than me and I had no business being her boss. I never let go of my analytics team, so I asked to step back into running analytics only. And continued asking for more stuff to try.

That’s when I got the opportunity to start a Growth team. Initially, I was extremely skeptical about the concept of a "Growth team.” Why would one team be responsible for the growth of the company, I thought… Isn’t growth everyone’s responsibility? But hey, it was something new and beggars can’t be choosers, so I accepted this new challenge nearly right away. This was very early in the timeline of Growth teams emerging—the only mature Growth team that existed at that time was at Facebook (And SurveyMonkey’s CEO was the Facebooks’s COO husband, so I assume the idea was shared over a family dinner). 

Growth that early was very straightforward: Find opportunities in data, then run A/B tests to try to move the numbers. That’s it. We already had an experimentation platform at that point that Product was using, so I took over ownership of it. I was still running my entire analytics team, but I also became an IC Product Manager, with one engineer to code things, so off we went. Our small team quickly proved its worth—we tackled SurveyMonkey’s viral loops, trial flows, pricing pages, and onboarding experiences. We earned the right to get more engineers and even dedicated PM resources. It didn’t take long for us to take on self-serve revenue accountability and an entire growth funnel: from acquisition to activation to monetization and retention.  My VP and SVP titles followed. 

I absolutely loved the job, integrating data insights with actionable, quantifiable changes. Needless to say, I became a ‘Growth team’ believer (check out how i define Growth team). This was around the time I met Brian Balfour who was just starting Reforge and became one of their first ‘featured guests’ talking about how to start and run Growth teams. This is where my growth network started taking off. As a last hoorah, I ended up taking on SurveyMonkey’s performance marketing team (overseeing SEO, SEM, website, and email), which fit very well into my growth world. 

Everything was perfect—I was running analytics, growth products, and growth marketing teams, loving my life. 

Then… the tragic passing of SurveyMonkey’s CEO, Dave Goldberg, led to significant changes in… everything. 

Most of my beloved leadership team left and I found myself stuck in the past—constantly criticizing new directions and wondering what Dave would have wanted to do. After a few executive coaching sessions, it was clear that I needed separation to grieve. 

So after 7+ amazing years, I started looking for a new job. I didn’t have the financial independence to take any time off, so I quickly jumped into a new role at Malwarebytes, a cybersecurity product. In retrospect, it was a wrong move for me. The cybersecurity industry was too slow for me and the company's culture wasn’t a good fit for me. 

After 2 short years, I quit. I was very confused. I was longing for another SurveyMonkey-like job, hoping to find another 5+ year home, yet I had no idea how to find it. I kept getting outreaches to be CMO/VP of Marketing... WHAT!? That did not seem like a good fit (after my PMM fiasco, I wasn’t planning on taking that as a full-time role). And the interview process for other Growth positions was so messed up. Never mind the lack of liquidity within the job and candidate marketplace (it’s all about your network, not the best match), but both parties were incentivized to just sell sell sell. Nobody was hiring for long-term retention. Nobody talked about hard problems. Everything was just rainbows and unicorns and sign a contract on the dotted line. All of which kicked me out of the market for full-time roles and opened up the world of solopreneurship to me. (At least until my recent return to FT, as VP of Growth at Dropbox!)

A bit of an unexpected journey, huh? Well, the reality is… most Growth leaders didn’t start in Growth:

• Casey Winters, who led Growth at Pinterest… started in analytics

• Brian Balfour, who led Growth at Hubspot… started as a product manager and a founder

• Ben Williams, who led Growth at Snyk… started as an engineer

• Melissa Tan, who led Growth at Webflow… started in investment banking and strategy

• Morgan Brown, who led Growth at Instagram… started in marketing and operations

• Adam Fishman, who led Growth at Patreon… started in affiliate marketing

• Hila Qu, who led Growth at Gitlab… started as a business analyst

This trend reflects the truth that Growth requires a particular mindset (growth mindset!) more than a particular background. And the cross-functional experience is often helpful, as you have to bring lots of teams together and it's good to understand their perspective.

My advice to you

If you’re considering switching careers or want to get into Growth, here’s my advice to you:

• Leverage your current company's opportunities. Use the relational equity you've already built, rather than convincing a new manager of your potential.

• Communicate your interests clearly. Let your manager know what opportunities you want.

• Be patient and flexible. This journey takes time, and flexibility can open unexpected doors.

• Aim for a T-shaped career. Grow to a director+ level in one specialty before branching out. Leadership skills transfer more easily than individual contributor skills.

But remember that you’ll have to find your own path, and don’t try to copy what I ended up doing. I never could have predicted all of this, much less planned it! If my experience has taught me anything… it’s to expect the unexpected. 

I wish you all the best on your journey, wherever it takes you!

Edited with the help of Jonathan Yagel—check out his awesome Substack.

Apply Now

Last week, after being an interim for 8 months, I accepted a full-time role to lead Growth at Dropbox.

For some, this seems like a major plot twist: I was a proud solopreneuer, I’m always talking about interim roles, and I even wrote a post about why I quit full-time roles! 

So, what’s going on? 

Well, to understand this decision, you have to understand the context of what took me out of the full-time path, in the first place:

My Solopreneur Journey

I started my career very much on a traditional career path, with a clear goal: get into leadership and possibly even become a CEO one day. That was the dream.

I had become a VP of Growth in my late twenties, led large teams, and had good company logos on my resume. But… I felt lost. It seemed as though everything I had worked so hard for wasn't at all what I had hoped it would be.

I was ‘successful’ professionally on the outside, but on a personal level, things were not going well. The weight of "mommy guilt" was crushing - I agonized over not spending enough time with my children. My relationship with my husband suffered due to the lack of quality time together. I gradually lost all my friends because I simply had no time for them. As I kept climbing corporate ladder, my career increasingly defined me, and I was losing my sense of self.

But that wasn’t even the worst part. The stressful nature of my work had a huge impact on my health. I couldn’t sleep through the night—and when I did, I was writing and rewriting Slack messages in my sleep. I frequently skipped meals, relied on wine each night to unwind, and found myself becoming increasingly short-tempered, agitated, and perpetually tired. That’s when I started using WHOOP, a device that measures your Resting Heart Rate and Heart Rate Variability. I was shocked to discover that my vital signs were similar to those of an 80-year-old woman on the verge of a heart attack.

This was a wake-up call I couldn’t ignore. I decided then and there that I wouldn't become just another typical Silicon Valley statistic—a 30-something suffering a heart attack on the job.

So five years ago I quit my full-time role. 

And had nothing else lined up, which was absolutely terrifying but intentional—to give myself room to figure out what I should do next. This is where my solopreneurship story started.

I didn’t leave my full-time job to become a solopreneur. In fact, when someone first called me that, I had to look up the term—I was clueless about it. I quit… to find another full-time role. I wasn’t ready to give up on being an operator; I just wanted to be selective and find a position that was a good fit for me: one that I would enjoy, where I could maintain physical health, and that would also allow room for a personal life. I had heard of such roles and believed they existed, but I was skeptical about finding them through the traditional recruitment process. Why? Because every interview I attended felt the same—it was all about selling (and even flat out lying), from both sides. The entire process seemed designed just to get a butt in the seat. No thank you.

So, I decided to start doing advising as a method to select my next full-time job. I gave myself a six-month window to ensure that my resume didn’t develop a significant gap and I remained relevant in the market.

I applied what I call 'Growth 101 tactics' to myself, treating my brain as a product. My monetization model already had a full-time ‘SKU,’ but I wanted to introduce an advising ‘SKU’ to the market. My ultimate goal was for one of my advising engagements to convert to a full-time ‘SKU.’ Advising was an adjacent use case to me, so I needed to find Product-Market Fit (PMF) for it. PMF involves understanding a problem, offering a solution, and having a distribution system. The problem I had a lot of expertise in was companies needing help scaling or introducing Product-Led Growth (PLG) business models. My solution was to offer my expertise, specifically where there wasn’t yet the need for a full-time VP of Growth or they were promoting someone in-house and wanted to set them up for success. I was going to meet my advising clients on a weekly basis for an hour and help them with anything ranging from PLG strategies to execution details. My positioning was: Scaling or introducing B2B PLG. I kept it very niche to differentiate myself, but in the big enough moat (TAM) and fast moving waters (space was growing). My distribution channels to find new clients were my LinkedIn and Reforge community. Reforge helped me get started—I had actively participated as a featured guest in many courses and was known for my growth expertise, which provided me with initial traction. LinkedIn was my diversification from Reforge dependency.

This strategy quickly brought in my first few clients.

I was surprised to learn how much I enjoyed advising. It was patterns galore—instead of building a deep sense of expertise in one company, I was able to see the trends across ~10 businesses at the time. It was fascinating. I truly realized that nobody’s problems are unique and I began developing frameworks for solutions. 

As 6 months passed, I stumbled upon my first interim role from one of my advising clients—Miro. I took it. This was my first pass into true solopreneurship as I began introducing even more SKUs to the market. I expanded my offerings to include my own Reforge courses (starting with the Experimentation course, then Monetization, Growth Leadership, and PLG course), paid public speaking engagements, growth workshops, interim roles, and this newsletter with paid archives and sponsorships (This diversification is what distinguishes a solopreneur from a freelancer, who only have one ‘SKU’).

I built up financial stability, found the work very interesting, and gained full independence. I was a happy solo camper, and my initial 6-month trial turned into one, two... five years of being solo.

.… which brings us to last week.

Back in the FT game.

After five years of thriving as a solopreneur, I decided to take a full-time role with Dropbox. But why, especially after loving the independence I had?

One of the major lessons for me over the last few years is that careers should not be linear. The goal for everyone should be to create as many options as possible, enabling you to make the best choices at any stage of your life. My solopreneur journey was nothing short of transformative—it revitalized my health (my heart vitals are normal!), strengthened my marriage, brought me closer to my children, and taught me SO much about PLG. I even expanded my personal ‘positioning’ to include product-led sales! I am genuinely happy and fulfilled. 

My initial engagement at Dropbox was on an interim basis (just like Miro, Netlify, Amplitude), but I found myself in a particularly amazing team (it’s always about the people in the end, isn’t it?) and solving a problem that was squarely within my superpower zone which I wanted to see all the way through. Dropbox was also willing to make it worth my while financially and respected my personal boundaries (no work after 6pm, non-negotiable 1 hour at the gym, and lowered travel requirements). So, after 8 months as an Interim, I converted to a full-time role. This approach allowed me to completely de-risk this choice, and I could not be more confident in this decision. 

Having the option to choose between continuing as a solopreneur or taking a full-time position is a privilege I don’t take lightly. I worked really hard to not *need* a full-time job, but choosing to accept one that was right for me. And after this role runs its course, I will return to solopreneurship. Because once a solopreneur, always a solopreneur :) And to be clear, I will be maintaining my solopreneur foundation with this newsletter, the Reforge courses, and my advising roles (although speaking engagements and most growth workshops will need to be paused). 

Should you still explore being a solopreneur?

The most valuable career advice I can offer is this: don’t fixate on becoming an executive, or a founder, or a solopreneur, or [insert your dream role here]. These shouldn’t be seen as ultimate goals but rather as options you should work to have available to you. Aim for the ability to choose your path freely at any point in your life. 

Career optionality is a priceless key that unlocks many doors.

Thank you for following along with my journey so far—there will certainly more twists and turns ahead. But as I’m focusing on growing Dropbox for now, I can’t wait to share all of the insights I’m discovering with you!

Edited with the help of Jonathan Yagel, checkout his awesome Substack.

Apply Now

"What do you do for work?” 

Does hearing this question freak you out? Excite you? Or do you just kind of answer on autopilot?

If you’re inclined not to take the question too seriously, beware: Whether you like it or not, this seemingly simple inquiry will instantaneously categorize you within the social hierarchy. People use it to decide whether you are worthy of their time and respect. For instance, if you’re at a networking event in Silicon Valley, it will go something like this: ‘Oh, you’re a VP at Dropbox? How fascinating, let’s connect.’ ‘Oh, you’re a marketer at a pre-seed startup? I’d like to find someone more ‘important’ to talk to.’ Of course, nobody will say it to your face (although some VC might)… they will just find an excuse to switch into a different conversation. But everyone knows. Here, respect and attention are often contingent upon possessing a leadership-level title from a well-recognized company. 

So, what’s the solution? Land bigger and better titles that win more and more respect? Unfortunately… that won’t work.

The Title Trap

We are social creatures and look for the validation of those around us—that’s totally natural. When you add in the fact that people often judge us by our titles, it’s understandable that we start to fixate on that one shiny set of words that comes after your name on your Linkedin, business card (do people still have these?), or email signature. We tie our identity to being an [X] role at [Y] company and begin a quest to level up “Once I land that this title at that company, then they’ll respect me!”

You may already see where this is going.

This pursuit of external recognition and validation begins to favor a linear and somewhat superficial progression through the ranks and fosters detrimental behaviors. Without even realizing it, this approach can lead you to feeling trapped. Here’s what I mean:

1. Trapped under superficial achievements.

For starters, the relentless chase for higher titles can lead individuals to prioritize superficial achievements over actual learning. One primary example of this: People choosing the quicker ascent to a coveted VP title through job hopping, rather than enduring the painful-yet-necessary experience of growing within a single organization. You can often jump up a rank (or even a couple) on the corporate ladder by switching companies, but the reality is that convincing a hiring manager isn’t the skill set that will make you good at your job. If you’re trapped in a bad situation and have learned everything you can from your current role, then by all means: Make the jump. But if it’s merely a matter of impatience to reach the next professional summit… you could be setting yourself up for disaster.

Unfortunately, I’ve seen too many people take this approach and land the biggest roles of their lives by hopping jobs… only to realize they’re in way over their heads. This can begin a cycle of overpromising and underdelivering that leaves a trail of business failures and destruction in its wake. And even if folks begin to realize it, they feel trapped—if they step back to gain the foundational experience they skipped over, it’s a huge ego hit. Very few can tolerate that, so they keep pressing forward.

2. Trapped in a Traditional Full-time Roles.

The fixation on titles and company logos can also trap individuals in traditional full-time roles that may not align with their skills or aspirations.  When I first started exploring solopreneurship, my biggest fear was whether I would stay relevant… Because I truly believed that my *current* VP title was the only way to signal the value of my accomplishments to the market. I eventually disproved this theory for myself, as I feel even more relevant now as a solopreneur than when I had traditional full-time roles, but it took me well over a year (or two) and a lot of self-reflection to get there. 

3. Trapped under External Expectations.

Perhaps most concerning is the inclination to make career decisions based on perceived market expectations rather than personal happiness and well-being. This mindset propels individuals down a path not of their choosing, driven by the desire to conform to societal benchmarks of success rather than pursuing what genuinely brings joy and satisfaction.

4. Trapped in a Never-ending Cycle.

This is the real kicker. If you think that getting a particular job with a particular company will give you everything you ever wanted… it won’t. Even someone with what you consider to be your dream role still probably wants their boss’ job. Or they want the same job at a bigger, more successful company. And if you go all the way to the top… well, would you say that Elon or Bezos or Zuck live perfect, worry-free lives? Me, either.

Don’t believe me? Send a message to someone with your dream job and ask: “Are you happy?” If they are, it probably isn’t because of their job title.

–

Okay, so, obsessing over job titles and external career progression doesn’t seem to be the solution… what is?

A Different Approach

How do we escape these traps? The answer is simple, but not easy: We have to distance ourselves from the idea that our worth is intrinsically tied to our professional titles. Such a shift in perspective encourages a more holistic view of success—one that values personal growth, happiness, and the pursuit of roles that truly resonate with our individual talents and passions. 

Personally, this realization led me to leave Silicon Valley for quiet suburbs in Tennessee in hopes of distancing myself from an environment where my self-worth was increasingly defined by external perceptions. Making this transition may require some mental, emotional, and social shifts for you, too, even if a physical move isn’t in the cards.

But even then, this is still very difficult. Just because you’ve realized that you’re not defined by your job title… doesn’t mean that other people will get that. Aside from intro conversations with strangers, this question comes up all over the place.

Take a quick glance at LinkedIn profiles and you’ll see what I mean: Every time I see someone with credentials like "CMO, Ex-Google, Ex-Microsoft" as their profile headline... I feel conflicted. On the one hand, they get it: Whatever their current role is, it doesn’t have the same pedigree as their previous positions, so they’re trying to signal to others that they’re part of the in-group. On the other hand, it makes me feel sad: It's disheartening to see individuals anchoring their self-esteem to their corporate affiliations, equating their professional worth with the jobs they’ve held in the past, regardless of the actual satisfaction or impact derived from those roles.

So, I think that’s the second part of this: After looking yourself in the mirror and acknowledging that you are not defined by your job title, you also need to figure out how to talk about what you do. 

My recommendation: Share what you care about, what gets you excited about your work, what you feel uniquely capable of doing. Enthusiasm is difficult to fake and people tend to remember someone with visible passion in their eyes. Whatever level you’ve achieved, this approach will help you align your conversations with what you actually care about. 

And if you can figure out how to communicate what’s important to you and someone still ignores you… that’s a pretty good indicator that they’re not worth your time, anyway.

So, what do you do?

-Edited with the help of Jonathan Yagel, checkout his awesome Substack.

It’s 2024, yet we live in a world that still confuses women's assertiveness with aggressiveness. A world where the words 'You're too aggressive' coupled with the seemingly innocent suggestion to 'smile more,' aren’t helpful advice—they’re a reflection of deeply rooted biases that feel diminishing, hurtful, and plain unfair. For countless women, myself included, such comments are not just an assessment of behavior but a stark reminder of the tightrope we walk daily.

Trying to be ambitious and assertive while also meeting old-school ideas of how women should act feels like an impossible act. Plus it hurts to think that the path to success is paved not with skill, but with compliance to outdated norms that equate femininity with being passive, nice, communal, and perpetually pleasant. 

I got feedback of being too aggressive many times throughout my career. One of those times, I pushed back. I gave an example of my male colleague who was getting promotion after promotion, despite being an absolute dick. I was sternly told to not compare myself to others as everyone’s path is different. I needed to be nicer and prioritize the feelings of those around me to succeed… okay? 

The irony is bitter.

In the pursuit of career advancement, women are often told that niceness is the key to unlocking opportunities, which couldn’t be farther from the truth. Because smile too much, and you will be questioned for not being serious enough. Be too nice and you’ll be labeled for not having enough drive. In reality, ‘niceness’ morphs into professional shackles that reinforce limiting perceptions of what a ‘successful’ woman should embody.

Assertiveness, on the other hand, is a trait celebrated and encouraged in the corporate world. Equated and correlated with success, even. But it’s a battleground for women. This distinction between assertiveness and aggression—a line so finely drawn yet so heavily policed—is at the core of this argument. Assertiveness, with its roots in confidence and clarity, is about standing firm in our convictions and advocating for ourselves and our teams with respect and purpose. Aggression, in contrast, is marked by a disregard for the perspectives and well-being of others. Despite these differences, the label of 'aggressive' is hastily applied to women who dare to speak with authority, challenge the norm, or simply stand up for what they believe.

So remember, by labeling women ‘aggressive,’ you pressure us to fit a mold that is both uncomfortable and unrepresentative of our true potential: silencing our voices, diminishing our contributions, and stalling our career trajectories.

I still remember the last time somebody told me to smile more, as if it were yesterday. Seven years ago, my boss was about to go on stage for an all-hands presentation, with me sitting in the front row. He locked eyes with me and used his fingers to drag the corners of his mouth up, sending a clear message I should be smiling. In front of everyone. I felt humiliated, furious, and ashamed. I wish I had just walked out, but I didn’t. I put on a grin, while fuming on the inside. But I complied, which I hate to this day. Needless to say, I ended up leaving that job within months.

And don’t even get me started on motherhood, which traps us in a relentless tug-of-war: society insists moms have to dedicate their lives to children (or you are a bad mom, obviously), yet at our jobs, the work has to come first (or you are a bad employee, obviously). Leave the office early because the baby is sick one too many times and expect to start hearing feedback that we are not motivated enough, we don’t want it bad enough, we are not focused. But heaven forbid we choose not to have children—the whispers of future regret are deafening. 

It's exhausting. 

But ladies… There is a light at the end of the tunnel. Once you break through the VP ceiling, your so-called aggressiveness magically transforms into your highest praised quality: assertiveness. I’ve seen it first hand with my own career. Nobody has told me to be nicer or smile more since I’ve established myself as an exec. Maybe nobody dares to anymore.

Just as an example, here is an excerpt from my most recent leadership assessment:

Elena is rational, direct, and extraordinarily competitive. She zeroes in on and pursues opportunity without registering the emotional or procedural cost involved on the way to success. Elena’s leadership is rooted in a desire to make a profound impact; those who contribute will remain close to her and those who don't will realize she has moved on quietly without them. 

This was a good, honest review of my capabilities. But earlier in my career, this same description would have been wielded against me as an indicator of aggressiveness.

The hardest part is to stay authentic and not conform to societal norms. As we embrace and accept who we are, we pave the way for a new definition of leadership—one that values diversity of thought, boldness, and integrity over niceness and superficial charm. The question is how to apply it in the most effective way within any given organization.

Never underestimate the power of a supportive manager, but I’ve also adapted to using  ‘weak language’—and it works like magic :) Direct, assertive language worked well for my male counterparts but was met with resistance coming for me.
So, instead of saying: 'This is direction. Let's execute.'
I'd use a weak language and say: 'This might be a better direction, don't you think?'

This so-called weak language is an unappreciated source of strength. It got me to the desired business outcome faster, built stronger allies, and supercharged my career. So I adopted it as a norm. Most women in leadership have.

Adam Grant notes:

In one experiment, experienced managers watched videos of people negotiating for higher pay and weighed in on whether the request should be granted. The participants were more willing to support a salary bump for women — and said they would be more eager to work with them — if the request sounded tentative: “I don’t know how typical it is for people at my level to negotiate,” they said, following a script, “but I’m hopeful you’ll see my skill at negotiating as something important that I bring to the job.” By using a disclaimer (“I don’t know …”) and a hedge “(I hope …”), the women reinforced the supervisor’s authority and avoided the impression of arrogance.

The leadership journey is full of challenges for any woman.

But together our voices can shatter the glass ceilings built with outdated norms, paving the way for a future where success is defined by talent and tenacity, not by how much we smile. 

I look forward to a future where being a strong, assertive woman is celebrated across all industries, job levels, and job types. 

Edited with the help of Jonathan Yagel, check out his awesome Substack.