TWH#56: Becoming a Startup VP Engineering
On preparing yourself for the opportunity to do work that matters.
When I started my career journey back in 2003, I had no idea what a startup really was, let alone a VP of Engineering. More than a decade later, on the very first morning of 2015 I landed in gloomy Berlin, the streets littered with the remains of the fireworks the city is known for during New Year’s. All I had with me was a large suitcase, and a signed contract to work at a small startup as a backend developer.
Three and a half years later, I got another one-way plane ticket, this time to Vienna, to become the VP of Engineering at a startup there. And another couple of years down the line, I moved back to Berlin and did it again. Still, my experience as a startup VP of Engineering is limited. But I did learn a fair bit about leading engineering organizations.
Although I find there is a shortage of content on how to do the role effectively, there’s even more scarcity about how to get the role in the first place. I have helped a few people land these roles so, if being an engineering executive is somewhere on your horizon, I have a few thougths to share:
What game are you playing? Why do you want to be a VP of Engineering? What will having the job give you that you don’t have right now, or that you can’t have any other way? Personally, I had been collecting ideas about running teams for a while and wanted to have the agency (and accountability) to deploy those ideas. Later, I wanted to make a dent in creating workplaces where people felt respected, safe in trying things, able to be their best, and to keep improving themselves.
Be a polymath. Being a successful VP of Engineering is more art than science. Be ready for when the opportunity arises by reading widely, across different disciplines—neuroscience, psychology, and complexity are particularly useful. Listen to all sorts of podcasts. If you come across something that resonates with you, reach out to the author and let them know. Ask a curious question. The best candidates are both interested and interesting.
Understand the role. There is no universal definition for VP of Engineering. It’s heavily context-dependent—stage of the company, whether it’s a service or product company, the composition of the existing team… the list is long. Find other VPEs and try to meet as many as you can. By exposing yourself to many different looks, you’ll start grasping the nuances as well as the patterns and challenges of the role.
Develop your philosophy. What uniquely defines you as an engineering leader? What do you care about and value the most? What do you strongly believe about leading engineering teams? For example, through my journey I became a big believer in the idea of creating leaders, not followers, and that decentralizing decision-making is imperative to successfully scale. Or that the relationships between parts of the system are even more important than the parts themselves.
Sharpen your writing. For me, there’s nothing that comes closer to a superpower than writing well. Every email, every message, every document, every code review is an opportunity to write better. Start your own newsletter. Write short LinkedIn posts. If you take this skill seriously, that puts you in the top 1%. To improve your writing, you must improve your thinking. And, interestingly, to improve your thinking, writing is of the essence. Put in the work. It pays off.
Create your filter. Hiring processes and interview loops for VP Engineering roles can be lengthy. This makes company selection even more critical. Most often, these roles get in front of you through executive recruiters and it’s on you to help them help you. Think of your “filter” as a one-pager to share with them that clearly defines what you are and are not interested in. This clarifies your own intentions, increases your chances of finding a good fit, and saves you hours of useless interviewing. Remember: every company has challenges. The question is what challenges you’re willing to help with, and with whom. (Here’s an example filter of mine)
Focus on their problem. 100% of the companies out there are hiring to solve their problems, not to be fascinated by what you did or who you are. If you want the role, your job is to help them connect their problems to you as a solution. That requires doing all you can before, during, and in between interviews to understand the specifics of their world, so you can speak to that. Avoid spouting generic engineering leadership stuff, or simply rattling off what you did in the past. If it’s not in some way connected with their reality, it’s of questionable value.
Roman philosopher Seneca once said, “Luck is what happens when preparation meets opportunity.” The tips above are exactly about being prepared when the opportunity to land a good VP Engineering role strikes.
Always be preparing. Remember that no matter your current role, odds are it’s a playground to exercise and hone all sorts of skills that make for a great future VP Engineering. While there’s a few responsibilities that only come with the actual role (e.g. sitting on a senior leadership team, managing a budget, etc), even being an engineering manager of a single team is in many ways a smaller version of what a VPE does.
Frame it that way, and every day is a learning opportunity.
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Until next week, have a good one! 🙏