Inside my first months at PostHog

Dec 12, 2024

I never thought it would happen to me.

I was an ambitious kid, and I always paid close attention to successful people talking about their careers on TV. A lot of folks seemed to love their jobs.

I wanted that someday.

But two decades into my career, nothing had really clicked. I liked aspects of some jobs. I liked certain kinds of work.

Still, over and over again, familiar dysfunctions showed up in the workplace. Sometimes I would complain, pitch changes. Sometimes these were adopted, but most times I was dismissed as an impractical idealist.

Or worse: a malcontent.

So I gave up on ever liking a job. Eventually I gave up on jobs altogether, hoping to scrape a living from a pile of grit and contracts.

Then I found PostHog. Two months in, I’m still finding the experience to be weirdly liberating.

Why? I'm still learning and decoding how it all works, but it seems as if everything that made previous work environments oppressively painful can be solved through simple, deeply honest hygiene.

Honesty from leadership

It’s an all-remote workplace, with an aggressive focus on writing things down. But that’s basic, everyone knows that advice.

What feels distinct is that PostHog’s small executive team doesn’t exempt itself from this approach.

My experience of the typical job is that executive decision making is a rat’s nest of hand-waving, loose reasoning, and ass-covering.

But my first week on the job, I saw our co-founders writing up some mundane, quarters-long failure of their assumptions, extracting the lesson that could be learned from it.

This sat in a GitHub issue, in an internal repo anyone could read.

Every quarter we all get to read the same income statements investors do. This is only proper: we are all of us investors ourselves, after a fashion, deferring cash today for equity we hope to increase in value tomorrow.

I got into startups 14 years ago, but I’ve never gotten this degree of transparency at work. Transparency keeps leaders honest, and this filters down to everyone.

Rigor enables autonomy

I’ve been here two months and no one has made me look at any tedious slideshows.

Slideshows are the refuge of the corporate snow job artist. A means of eliding detail through headlines and text that never quite coheres into an argument, and never finds itself as a useful reference in the future.

Instead, I sat down after lunch on my second day to read PostHog’s handbook. It’s public, you can read it too.

From the beginning it lays out actionable, logical arguments:

• The advantage our business seeks
• How we seize that advantage today
• How we structure the business to maintain leverage in the future

From there, it breaks into fractal detail for each area of the business. How engineering works, how we approach design and marketing, what you need to know about HR.

Alignment doesn’t come from endless meetings and slides. I think it comes from everyone having an independent but accurate understanding of what the business is trying to do, and how they themselves can be part of that adventure.

But getting there takes ongoing rigor, documented in shared artifacts that let everyone learn the business, not just their own job in the abstract.

I know how PostHog wants to win, and how to do my part in it. Being rigorous prevents hand-waving from taking over the business.

360 feedback

I’m blessed and cursed with inspiring strong reactions from people. Some of them nice! Others more complicated.

It has always been this way. In the typical organization, though, I’ve not found particularly strong release valves for strong opinions.

A quarter into my second job, post-college, my boss blew his top at me, and we both spent a good half-hour crying and talking it out.

The alternative is deliberately-designed, ongoing 360 feedback sessions among teammates. 45 days into this job I got to hear candidly what people liked, what people wanted more of, and in a few cases, what people found grating in me.

This gives me information to make better choices. I can evaluate the feedback and decide to lean further into places where my strengths are meshing with the team’s needs. I can make more intelligent tradeoffs between my ambitions and how my style impacts other people.

Instead of being in the dark, I can navigate with confidence. Consistent feedback prevents resentments and poor direction from building up.

Fluid org chart

The org chart is, in most places, treated like some holy truth carved in stone. It doesn’t readily change, except in calamitous, company-wide ruptures that change everyone’s lives overnight.

Alternatively, you can build teams as small squads, forming, dissolving, and combining talent as the needs of the business evolve.

Every now and then I’ll look over my shoulder and see a new team has formed, cleaving off from previous work to start a new adventure.

The flexibility has obvious advantages for the business, but for people, it’s an antidote to stagnation. The org chart evolves to suit the best fit of people on it, instead of trying to bend them into an imagined shape that doesn’t work. I can’t tell you how many people I’ve seen burn out because they couldn’t quite manage to become what someone randomly wrote down in a doc 18 months earlier.

Instead, when we notice such a mismatch, a team’s actual strengths can be codified, and new teams can be chartered to fill any gaps. This is the luxury of a business that’s healthy and growing: slack in the system to also evolve.

Even better, the org chart is descriptive, not prescriptive. It’s not a declaration of turf.

I got to ship a new feature for our data pipelines product in my second week. That’s not even my department¹. So damn much fun.

Operational curiosity

It is impossible to know everything in advance.

A common startup failure mode is the tyrant founder who assumes he knows better than anyone else what must be done, what will work, where to go.

But certainty is a trap for anyone trying something genuinely new. Curiosity, meanwhile, is the path to constant opportunity. You can’t know until you try. You can know even more if everyone is entitled to try.

So everyone at PostHog is free to try, to fuck up, to discover. If I have a strong opinion that disagrees even with a founder, I have the option to give it a swing anyway, if the decision is reversible.

There’s not an aggressive process that dictates what I can do or how I have to do it. I have the trust of my team to make moves, and I’ll get feedback when I get it wrong. We course-correct into the right path through a sort of social eventual consistency².

Two guaranteed days of uninterrupted, deep work don’t hurt, either.

Periodically, teams will host an off-site where we get together to catch up and play around with technology. Open opportunity to experiment and learn new things is central, through a sedate and generous block of hackathon time.

In my first hackathon, I got to dive deep into the workings of the product itself. What does it mean that I now know the specifics of doing CRUD operations in PostHog? How will I leverage this additional insight in my role as a propagandist and communicator to developers?

I don’t know. And no one made me pretend to know ahead of time. I just got to have fun and explore.

I can’t wait to find out.

wtf, right?

I'm trying not to be too weird about it. I think my coworkers are getting used to my outbursts about how something makes way more sense than usual.

By month two I’m usually anxiously glancing at the exits. The endless paper cuts of structures that don’t quite work – but still bind the everyday of workplace existence – start to chafe and rub. Instead, I'm busily learning more and making plans for what I'll do next.

I didn’t think they still made startups like this. But the more I think about it, I’m not sure they ever did.