People, culture, product

Most people start thinking about what they want from a job when they're already looking for one. I think that's too late.

I spent three and a half years at Retool. It taught me a lot about work, the wider tech industry, and how to be honest with myself about what I actually value. Last month I joined PostHog as a Technical Account Manager. But this post isn't about that move. I want to write about how I think about choosing a company and role. I'll share more about PostHog another time.

Even if you're not actively job hunting, this is worth thinking about. Especially then, actually.

The shadow list

I've kept a list of companies for years. Not companies I was applying to. Companies I was watching.

The tech industry shifts quickly. Roles appear and disappear overnight. Companies you've never heard of become household names in months. If you only start paying attention when you're actively job hunting, you're already behind.

My shadow list was a running shortlist of companies that caught my eye but weren't hiring for roles that matched my skill set. Maybe they didn't hire in my region. Maybe they didn't need technical customer-facing people yet. It didn't matter. They had my attention. I'd follow their blogs, watch how their product evolved, and keep tabs on how they grew.

PostHog was on this list.

Three circles

Whether I was browsing a company on my shadow list or responding to a recruiter on LinkedIn, I found myself making the same mental calculation. Three variables: people, culture, and product. Not necessarily in that order.

Sometimes I'd write these down. More often I'd run through them unconsciously: scrolling a company's website, reading a news article, half-forming an opinion before I'd even realised it.

The perfect company doesn't exist. But if you draw a Venn diagram of these three circles, you want a company that sits as close to the centre as possible. Here's what each circle meant to me.

People

This is about the people I'd work with day-to-day. My peers, and the leaders setting the direction.

For peers, I paid attention to whether a company lets you interview the people you'd actually work with. That tells you a lot. A flat hierarchy helps too. Not too much focus on titles or layers between you and the decisions being made.

For leadership, I looked for founders and leaders who still talk about their own product publicly. Not outsourcing that to developer advocates or marketing teams (and I really appreciate the work those teams do). But when someone who built the thing is still the one explaining it on a podcast or a blog post, that says something about how close they are to the product.

I spent a lot of time listening to podcasts and reading blog posts before ever speaking to anyone. How a leader talks about their product in an unscripted setting tells you more than any careers page.

Culture

People are what make culture. That's what makes it fragile. It can disappear overnight if the wrong people leave or the wrong people get hired.

Culture's also the trickiest circle to evaluate from the outside. Everyone says they've got a great culture. The signal I found most useful: question it. Ask a company about their culture and then push back on the answer. How they respond to that tells you far more than the answer itself.

Benefits tell you a lot too. They're culture made tangible. A company putting its money where its mouth is. At both Retool and The Information Lab, there was a genuine focus on mental and physical wellbeing. That mattered to me. I've also spoken to companies with questionable reward structures. That told me all I needed to know.

Product

I need to be excited about what a company builds. The kind of excited where you're playing with it on a weekend because you want to, not because you have to. You'll spend eight hours or more every day working with this product. It needs to solve a problem you've felt yourself.

Retool clicked for me because I noticed a problem in the market. I'd seen companies trying to turn their BI dashboards into internal apps, hacking together writeback functionality. I loved building little integrations in Tableau to patch this, but Retool built a complete product around it.

PostHog was similar. I'd felt the pain of juggling five different analytics tools. A platform that consolidates them into one and gives product teams real autonomy.

Not all circles are equal

These three circles don't carry equal weight. Culture was the biggest for me. I want autonomy over my work. I want to be treated as an adult. Give me a problem and let me figure it out.

Product matters a lot too. I've spent years building up my technical skills and I don't think I'm done learning. If the product doesn't challenge me, I'll get bored.

People close behind. I want to work with people who challenge me.

What I've realised is that all three feed into the same thing: learning. That's what I'm actually optimising for. I want to learn something new every day. That's it. Everything else follows from there.

Your weightings will look different in the diagram.

These are my thoughts on what matters. Not just when I'm looking for a role. Before, during, and after. Start your shadow list now. Figure out your weightings before you need them.