10 Key Product Management lessons from 15 years in startups

Photo by incredible Anastasia Stashevskaya (Barcelona, Spain, 2024)

This year, I realized that I’ve spent 15 years in startups – Russian and European, early-stage and established, mainly digital – wearing multiple hats as a co-founder and in various product-related roles. Naturally, I wanted to draw a line and summarize what I’ve learned so far. Hopefully, this will help emerging product managers avoid some common mistakes and allow me to properly reflect on my journey.

Let’s dive in. Here’s what I’ve learned as a Product Manager so far:

To be clear, by execution I don’t mean project management (like moving Jira tickets around). I mean executing on a business strategy: doing what’s right for the company, prioritizing what needs to be done and making sure it’s done. It doesn’t matter if you’re a CPO, a PM in one of many squads, or the sole product person in a young startup. It doesn’t even matter if you’re a product person at all. Execution is the number one factor in achieving success.

Once you have traction and your users are somewhat happy, make sure they pay and aim to reach profitability as quickly as possible. Shit happens all the time, and the chances of a startup surviving it while being profitable and having some "fat under the skin" are much higher than the alternative.

I learned this the hard way during Covid while working in a startup with a very user-oriented culture: low commissions, loyalty programs, etc. It was tough to compete with more profit-focused players, and we felt the pain of lacking cash firsthand.

You can’t do everything alone. Even if you’re capable of doing a lot, your energy is better spent empowering and engaging your team rather than handling all the tasks yourself.

Why? Because diverse points of view and expertise lead to better outcomes. Because multiple eyes catch errors you might miss. Because when team members are involved in building the product from scratch, they treat it as their own, and their motivation grows exponentially. Because of the bus factor and scalability issues. And because no individual, no matter how skilled, can outperform a team of empowered, brilliant professionals.

Read more on how to empower a diverse team.

Remember point #1: "Execution = efficiency = getting the right thing done is the number one thing for a successful product."? To execute effectively, you first need to identify the right things to work on – and that’s impossible without a clear strategy.
Strategy is a well-defined list of problems a company needs to solve, in the right order. Spend time developing it. Involve your CEO and stakeholders in the process, ensure your team is fully aligned with it, and then stick to it.

You’ll inevitably face countless distractions and brilliant ideas to pursue, but with a solid strategy in place, managing them becomes far easier.

Feeling silly repeating the same thing over and over? Keep going—repeat more. Draw diagrams, record videos, give presentations, send Slack summaries, and discuss it in 1-on-1s until you hear your team members repeating it in their own words.

If you’re working remotely, double your efforts. Feeling 2x silly? That’s okay. It’s far better than having a misaligned team.

Embrace it – nobody does. We humans know very little about the world, but we’ve developed pretty good models that allow us to function successfully. Product management is no different. There’s no way to have all the answers upfront, but by relying on data, gut feelings, experience, and teamwork, you can build a strong foundation.

Treat everything as an experiment. This mindset helps you stay open to reality and continuously test your solutions against the real world. You will make mistakes. Not all your decisions will be correct. Customers will surprise you again and again, and that’s perfectly normal, as long as you learn and iterate.

Never let anyone convince you that you’re not good enough. If you genuinely want to work in product, you are good enough. If you don’t know something, you’ll learn – nobody is born with all the knowledge and skills.

If you don’t have someone to guide you, seek out a mentor or coach. They don’t have to be your current manager – not all managers are good mentors. If you feel pressured by authority figures at work or lack support, take the time to recognize it and make an effort to act on it.

Nothing is worse than a self-doubting product manager (or any executive). It’s destructive for both the individual and the team.

Culture is not about nationality, gender, age, education, or even shared experience. I’ve worked in all-Russian teams and felt like an outsider, and in European or American teams where I felt completely at home. I’ve worked with people my age and felt uncomfortable, while in younger or older teams, I felt perfectly aligned.

Culture is about respect and how it’s expressed. It’s about whether the pace is fast or slow, whether the mindset is growth-oriented or stagnant, whether rules are strictly followed or creativity is encouraged. It’s about transparency, responsibility, and ownership. It’s about how differences are treated, how communication is maintained, and what behaviors are valued or punished.

Culture is how people act when no one is telling them what to do – it’s the defaults and assumptions that guide them. Culture isn’t black and white, it’s not simply perfect or toxic. But it can either align with what makes you comfortable, or it won’t.

You can’t build a successful product without great analytics. You need North Star Metrics, KPIs, funnels, cohorts, and models to track changes in user activation, engagement, and retention in response to the features you build. However, if you rely solely on data, you’re effectively ignoring half of the information available to you. Chris Saad puts it best: blindly relying on data is like driving with your eyes glued to the GPS, ignoring the road ahead.

Agile is about delivering value and learning as quickly as possible. While this sounds simple, teams often fail to grasp what it truly means. I frequently hear statements like, "We’re agile" and "We need detailed specs for six months upfront before we can start development" in the same sentence.

For many, "agile" means working in sprints, having a Kanban board, and running stand-ups. I have bad news: that’s not agile. Bi-weekly deploys are not agile. Perfect code that is not deployed is not agile. Implementing a task simply because it was decided three months ago isn’t agile either.

I learned this the hard way during Covid when I saw what true agile looks like – how a non-Silicon Valley team could achieve incredible things in just two days. There’s always a faster way to deliver value or test a hypothesis.

These ten points are the most important lessons I’ve formulated during my 15-year journey. Interestingly, even though they may seem like common sense, it’s incredibly easy to forget them. We often fall into learned patterns, get caught up in daily routines, and overlook red flags like ambiguity, self-doubt, toxic culture, under-communication, and other issues. As a result, we can lose control of the situation. That’s why it’s helpful to revisit this list from time to time as a reminder of what truly matters.

I imagine someone might say, “Oh man, you forgot to mention X, and it’s the number one thing for a successful PM!” You’re probably right! Feel free to share it in the comments – I’d love to chat about it.