How I think about hiring

Cowboys and farmers, old guard and new guard.

‘Okay, but seriously: how do you achieve this level of velocity in the product and this level of noise in the market… with 200 people!?’ People ask me this all the time. It seems unreasonable, even unbelievable, how much is being produced by so few employees.

My answer is: It’s all about the team. And the team profile is not at all what you’d expect for a company that has $400M+ in ARR. It takes all types of people. Yes, we’re big on AI-nativeness, but that’s not all. You have to have the right blend.

So I’ve been telling people that you need farmers and you need cowboys, and you need old guard and you need new guard. And most importantly: All of these groups need to actually get along.

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Our hiring grid

Here’s how we think about it:

Cowboys and Farmers

A ‘cowboy’ thinks outside the box. They’re naturally pushing the boundaries and searching out new territory. They roam all over the place.

The ‘farmer’ is focused on making sure the cowboys have the resources to keep exploring. They grow food on the land that has already been acquired. They scale up the operations behind the roving horse-riders.

Without the farmers, the cowboys can’t go as far. Without the cowboys, the farmers just stay where they are.

Old Guard and New Guard

In this case, I’m not talking about just the company OGs (founding team, early employees) vs. new hires… I’m talking about industry-level experience: Seasoned vets vs. Wunderkinds.

What the old guard brings to the table is raw business experience - the ‘I’ve seen this movie before’ instincts to understand how things can go right, but mostly just 1000 ways that things tend to go wrong.

The new guard is where the AI native instincts really come in. These are truly people right out of school, who have never worked corporate jobs before. They bring the confident ‘well, why don’t we just do it this way’ perspective that the old guard tends to ignore. And now, because of how much AI is changing the fundamentals, they’re often right.

A note on young farmers and old cowboys

You may notice two areas on the graph that are a bit lighter - what I’d call ‘young farmers’ and ‘old cowboys.’

The ‘young farmers’ part is pretty straightforward: The operational infrastructure and scalability components require a lot of context. Having AI-native folks who can completely rethink everything is a huge asset in the innovation and market-facing roles. But the underlying systems almost always require more planning and experience. This is the place where you absolutely do NOT want to move fast and break things.

The ‘old cowboys’ part is… actually a bit personal for me. I’ve always taken a lot of pride in being on the ‘cowboy’ side of things: staying up with the latest technology, trying out the most innovative stuff. But the reality is that coming up through the previous waves of software and growth means that I’m not literally AI native. I wasn’t born into it.

Which means that I’ve got some catching up to do.

But I also think that these intersections are where you have the most opportunity for High-impact IC types - enough experience to have an impact and build something scalable, but enough AI literacy (and organizational role freedom) to go chase things down on your own.

Which ones do you want? Yes.

For companies at our size, the instinct is usually to hire Farmers. Usually, the cowboys come first (and later, when you hit a new PMF horizon), but the classic move for a scale-up is to put down roots and start harvesting revenue. Farmers love Growth, amirite??

But in fast-moving environments, you can’t just go all in, in one direction. Yes, you do need more farmers. But you also need to be bringing in lots of cowboys, to keep things moving.

So, as we’re building out teams, we’re not just looking for a generic ‘marketing specialist’ or ‘PM for this area.’ As we evaluate talent, we figure out the area and then start thinking about the fit: ‘Which quadrant do they need to fall into, to be impactful in this role? And most importantly: how do we make sure that there’s a good representation in each quadrant on the team, to maintain a healthy tension?’

You need all of the different components, plus mutual appreciation across the sectors. You have to find the right balance: Innovation plus scalability, industry expertise plus willingness to reinvent everything.

How do you actually hire for this?

Unfortunately, you can’t just ask people which category they’re in. A lot of times, people don’t even know themselves! So it’s not something you can screen for in a 30-minute or hour-long interview.

This is one of the reasons we’re really big on case studies and trial work at Lovable. Trial work makes a huge difference: Come in and work with us for 2-3 days, and you’ll get paid for it. Then, you can kind of see the environment and what it’s really like, and we can see you and what you’re capable of doing. This generally works out quite well because you can tell very quickly, once you actually get into the work with someone.

We also often start people as contractors and then convert them to full-time, if possible. In fact: even I started out as a contractor. I converted to full-time, 6 months in. This was good on both sides: Not just because they were able to test me out, but because I wasn’t even sure if I was going to be a good fit in the company. So the contract-to-hire route doesn’t have to be limited to just entry-level jobs. You should consider applying it as an experiment for bigger positions, as well.

How do you build the right culture?

Maybe ‘hey, you need different types of people in your org’ sounds obvious, but the hard part is getting these different types to work well together. The way to do that mostly comes back to humility. Which is another thing to hire for. But a few things I’ve noticed for how our org is set up also help.

(1) Nobody gets internal titles. The hierarchy is almost entirely flat. There are the people doing the work, and some Leads, which have a bit more responsibility. And there are department Heads, who have at least 2+ levels underneath them, but there are less heads than I can count on one hand. We’re trying to keep everything super flat.

Taking titles out of the equation shows the motivations for why people want a big title in the first place. Either: (a) Title is an important thing for your ego (which I get… everyone goes through this), or (b) People NEED the title to get work done.

That second type is the structure that creates an environment where the old guard can’t collaborate with the new guard. For example, if I’m the VP of Growth, a new grad would have a hard time doing face-to-face work with me, even if I’m very supportive of it.

I’ve had to check myself a couple times with this, when new grads are pushing back on things that I think are obvious. It teaches me humility! I love it. It keeps me accountable, and it turns out they’re right a lot of the time. People with limited experience aren’t always right, but they usually have great perspective that is generally suppressed in most organizations.

(2) Autonomy and agency as a core value. At Lovable, everybody can make a decision. They’re the ones who are accountable and responsible. There are a few exceptions, but in general, decisions don’t have to travel up and down a chain of command. If you can convince one person, you can move forward. It doesn’t have to all be top-down, from the Old Guard / senior people. Everyone is empowered in their role to own something from end-to-end. You’re actually expected to only pull people in when you need to. This creates equality in the org and removes the permissioning, which is so important.

(3) We appreciate people who are comfy with chaos. This one is probably harder for the OGs (like me) who are maaaybe a bit addicted to data-backed decisions. But the tough reality is that when things are evolving this quickly, there will never be enough context or ‘alignment’ to know for sure what will happen. We need people (whether Farmers or Cowboys) to just call the shot so that everyone else can move forward. I’ve been so impressed with my coworkers who create this kind of clarity for the whole org. Sure, admit the tradeoffs and show the risks, but we have a shared agreement that waiting for perfect information would keep us in a holding pattern forever.

What should employees and job applicants be doing?

Now, what should you do if you’re reading this and want to make yourself as hireable as possible?

My suggestion:

• Step 1: Be honest about where you are, right now. Like I said before, it’s shocking to me how few people are aware of where they fit on the chart.

• Step 2: Lean into your superpowers. Are you naturally more focused on disruption or structure? Do you have tons of industry experience, or do you bring a fresh perspective? Start there.

• Step 3: Consider where you want to grow. The old guard needs to understand AI-native capabilities, even if they probably shouldn’t be bleeding edge. The new guard should work on growing their context window (to use a term that will make sense to them, lol). You should play to your strengths, but understand where gaps might exist, so that you can at least watch out for them.

• Step 4: Appreciate your counterparts. Become BFFs with the other quadrants. You need what they have, they need what you have! You can help each other out, and don’t be too proud to ask for feedback and input.

All of this starts with developing enough self-awareness to know where you can be valuable and leaning in there.

Companies today are growing so fast that these types of collaborations are absolutely critical. Having this kind of understanding for the structure of different roles helps everyone to appreciate each other more, and thrive in the things where they can offer the most.

Happy trails, y’all!

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Edited by Jonathan Yagel.

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