The biggest takeaway from my Stripe Sessions talk
Treat pricing and packaging like a product, not a policy.
Last week, I gave a talk at Stripe Sessions, and now I’m even more convinced:
Most companies seriously underinvest in monetization as a growth lever.
(Side note - when did Sessions get so big??? 6K+ people showed up and I’m hearing it’ll be even bigger next year. Wow. Definitely not an event to miss.)
They obsess over acquisition channels, activation funnels, retention curves, and roadmap prioritization, while pricing and packaging get treated like a dangerous object in the corner of the room. Something to avoid touching unless absolutely necessary.
That mindset is costly.
Because monetization is not just how you capture value. It is one of the most powerful ways to create growth, improve customer experience, and adapt to changing markets.
At Lovable, one of the biggest lessons from the last year has been that pricing should be treated much more like product than policy.
Elena’s Picks
Hey, I’m trying out a new format! I’ll be specifically featuring products and services I personally recommend to this community. Plus, sometimes a few that I’m exploring.
→ Stripe: The monetization infrastructure you actually want. They’re an essential part of our growth work at Lovable, and I use them to manage payments for all of my solopreneurship stuff, too. If you’re considering alternatives… don’t. Just use Stripe.
🎁 Offer: Playbook for scaling AI product pricing. How are we supposed to price AI products, exactly? Stripe put together the 5-step framework you need.
→ Factors.ai: Here’s one I’m exploring: The problem they’re going after? Running ABM campaigns manually and across a bunch of different platforms. Factors.ai has an agent that pulls together visitor identification, intent data, ABM activation, and multi-touch attribution. How much better could all this be if it’s all in one platform?
🎁 Offer: LinkedIn Benchmarks report. Want to know how your LinkedIn strategy stacks up? Check out this free report, based on an analysis of 100+ b2b companies.
→ Lovable: What can I say? Yes, I work here. But… I work here because I was obsessed with the product, first. It’s the best way to build an app or site, even if you have no technical experience. Try it out!
🎁 Offer: Get a year of Lovable for free! (For paid subscribers to Growth Scoop)
Normalize iteration
In my first year alone, we changed pricing and packaging more than ten times.
We launched annual plans. Added credit rollovers. Introduced top-ups. Removed users as a monetization unit. Launched a new business plan. Added cloud and AI usage metrics. Expanded into new currencies. Ran targeted downgrade flows. Did promos (did you see our Lovable day on Feb 14th when everything was 50% off? Or our promo offering custom domains for just $1?). We rework and experiment with our monetization value repeatedly.
None of that created some mass customer revolt that people love to imagine. Customers adapted. In fact, over time, they began to expect our monetization model to evolve just like the product does. This makes a huge difference! Many companies accidentally train customers to expect static pricing because they never change their pricing and packaging. Then every future change feels shocking, political, or unfair.
A better model is to normalize iteration.
Just look at Netflix. Their early price changes made big headlines because they had conditioned the market to think pricing was fixed. Once price changes became part of the normal rhythm of the business, the uproar stopped. Customers adjusted.
Static monetization may feel customer-friendly in the short term, but in fast-moving markets it’s actually a trap. Costs change. Customer behavior changes. Product value changes. Competitive dynamics change. Of course pricing and packaging has to change, too!
Freemium all the way
Another takeaway from the last year is that freemium is STILL misunderstood. Too many teams treat freemium as a cost center. A trial of sorts. Something to minimize/hide, over-optimize for paid conversion, move functionality out of. They see freemium as infrastructure spend and support burden, and treat free users as second-class citizens (some don’t even consider them customers… which is wild).
That’s the wrong lens. Freemium should be evaluated as a strategic investment that drives your entire growth model: acquisition, activation, monetization, and retention. Lovable invested heavily in freemium last year. Not because we wanted to subsidize usage indefinitely, but because it was one of the most effective ways to get users into the product, help them experience value quickly, and convert when they needed more. But wait, there is more! We go even further - we give away our product through partnerships (like Lenny’s newsletter) and still see 40%+ paid conversion from those users.
At Lovable put our best product & model forward in freemium and treat freemium spend as a strategic investment - something to lean into, not optimize away. The result is double-digit free-to-paid conversion at serious scale.
Ungate your AI features
Another area where I think many companies that are adding AI functionality to existing products get it wrong is how they monetize it. The common instinct right now is to place AI features in the highest pricing tier. Teams look at LLM costs, worry about margins, and decide AI needs to be premium-gated.
I understand the logic, but it’s backward. AI is not just another feature. In many products, it requires customers to change behavior. They need to trust it, learn where it helps, and build new habits around it. And that’s not going to happen behind a paywall.
Customers usually need to experience the “aha” moment before they’re willing to pay a serious amount for AI-powered outcomes. Too many pricing models today are over-optimized around model cost and under-optimized around customer value creation.
In some categories, the better strategy may be to make AI widely accessible, let customers experience the benefit, and monetize the resulting productivity, speed, output, or scale.
Stop the subscription obsession
I also think many companies are leaving money on the table by overcommitting to subscription-only models. Recurring revenue is valuable. Predictability matters. But the ARR obsession has gone too far. Not every product maps neatly to monthly recurring behavior. Not every customer uses software in a flat, predictable pattern.
At Lovable, we launched top-ups alongside subscriptions in under eight weeks. Conventional wisdom said it would cannibalize recurring revenue.
It didn’t.
Our best customers purchased the most top-ups! And our retention improved. Customers were telling us their building patterns were streaky, and our monetization model needed to reflect reality. Some periods are high intensity. Some are lighter. Trying to force every user into a rigid subscription model can create friction where flexibility would create growth.
One of the clearest lessons from all of this is that speed matters. Many companies still run pricing changes like multi-year transformation efforts. Endless internal debate, perfect-model forecasting, stakeholder alignment, and months of hesitation. Meanwhile, the market keeps moving.
The best teams I know are running monetization more like experimentation. They test faster, learn faster, and adapt faster. They treat packaging, thresholds, units, and offers as evolving systems rather than permanent architecture.
If I were advising companies right now…
I’d focus on three things first:
1. Get your infrastructure right.
If every pricing change requires engineering heroics, months of billing work, or manual operational cleanup, your systems are slowing your strategy. Modern billing and payments infrastructure gives you the ability to iterate.
2. Figure out monetization ownership.
Monetization cannot be a side hobby spread across finance, product, growth, and leadership with no clear driver. Someone needs to wake up every day thinking about how the company prices, packages, experiments, and captures value.
3. Assume you DON’T KNOW the perfect model in advance.
One last note, which may be the most important: Teams need to remove ego from the process. A surprising amount of pricing strategy is still based on whatever the boss says. Or, as I like to say, the HiPPO (Highest Paid Person’s Opinion). It’s good that they have strong opinions, but that should be a hypothesis to test… not the final word.
Assume you do not know the perfect model in advance. Assume the market will teach you. Assume customers will tell you through behavior, not surveys.
Monetization should not be treated as a static spreadsheet exercise. It should be a living, breathing part of the product. Because if your product evolves every month and your monetization evolves every three years, you are almost certainly creating both missed revenue and worse customer experiences.
Thanks to the Stripe team for having me and for all you wonderful people who came up to say hello, after! Public speaking isn’t my favorite… but meeting all of you was!
Edited by Jonathan Yagel.
Love this write up Elena. And love Lovable’s monetization strategy. It fits what I need. Also, I don’t think I’ve ever ended a free service early to pull out my credit card and just pay for it, but I did with Lovable. I got so much value from Lovable in the first few days it (and obviously still do) that it literally felt wrong not to be paying for it.
"Too many teams treat freemium as a cost center. A trial of sorts. Something to minimize/hide, over-optimize for paid conversion, move functionality out of. They see freemium as infrastructure spend and support burden, and treat free users as second-class citizens."
"Lovable invested heavily in freemium last year."
OK, to get it fair, those two statements are not contradictory. Lovable invested in freemium in 2025. *And* it treated freemium users as second-class citizens. As anyone who has tried to do anything that the most basic play would attest.
Now, don't treat it as an attack on Lovable. Anyone looking at the financials would say that for an AI-heavy product, freemium must be heavily limited. From a customer perspective, it must be limited to a degree that's borderline unusable.
It's hard to discuss basic math. Free-tier users are not free for the product company. It said company offers value based on AI use, then free users are, in fact, very expensive (as compared to the old-school SaaS model). So who pays for them?
a) Paid users
b) Investors
c) Subsidized infrastructure deals, a.k.a., AI labs (which, in turn, means investors too)
Now, if paid users don't even pay enough to cover their use (because they don't, correct?), we can't rely on margins from paid tiers. Which leaves us counting on the investors to cover the gaps as we try to teach users that the prices will keep changing. A lot.
No wonder customers are increasingly used to frequent plan changes. An alternative way would be subscriptions that are 20x as much. And even then, people would find ways to abuse them. Still, the question is: how many customers would buy ChatGPT or Lovable subscription if it were $500 a month?