8 Career Patterns for CTOs

Whether you’re an engineering director, VP, or CTO, how can you craft your perfect career?

What is a “good” career for an engineering leader? What are some common career paths for mid-career engineering leaders?

Over the last few months, I’ve been having a lot of really interesting conversations with other engineering leaders about how they think about their careers. Once you’ve proven competence as an engineering leader, what is the right next challenge? I’ve noticed eight common approaches that I wanted to share.

1. Rinse and Repeat

I was speaking to someone a few months back who was the prototypical “Series A CTO”. Their sweet spot was turning a small, scrappy engineering team into a scalable organization. They didn’t want to waste their time on companies lacking product-market fit (lack of impact) and while they enjoyed coding, they felt that they had more leverage by managing a team. They were passionate about creating an engineering culture that cared about quality and work life-balance while still being pragmatic in terms of shipping features and solving business problems and they’d taken three teams from 5–12 engineers up to 50+. At the same time, they weren’t that excited about building a larger org. For them, it felt too bureaucratic and political and they liked putting the organizational structures in place to scale a team but had much less fun actually running such organizations for the long term.

They admitted that dealing repeatedly with the challenges of hypergrowth was exhausting, but it was also energizing, they knew where most of the pitfalls lay, and they also felt that it was their best opportunity for getting a meaningful economic return (they consistently negotiated extended exercise periods for their options) by having a (small) portfolio approach to their startup stock options.

New Adventures . . .

I also spoke with a number of engineering leaders who discussed their experiences of moving outside of their comfort zone . . .

2. Upsizing

The first had been acquired by a FAANG company while they were still running a small team and got the opportunity to have a smaller impact on a much larger code base. They enjoyed the compensation and the opportunity to build solutions that would impact many more people, but eventually they decided after three years to go back to their startup roots and build another company from scratch.

3. Downsizing

Another talked about the challenges they had faced when moving from an enterprise to an early stage startup. Both the difficulties in getting a role (I think most founders now realize that bringing enterprise executives into a pre-product-market fit company can be challenging) and the issues that they had trying to build everything from scratch without the kind of support and systems that you take for granted at a larger company.

At the same time, they also really appreciated the fact that decision making was so much faster and the team was both more engaged and more productive than the engineers they’d worked with in the past. The startup they were working for went out of business, but they ended up taking another startup role — this time at a Series B funded startup as the VP of Engineering where they could bring some more structure and discipline to the org while still having more impact and moving quicker than they could in their previous enterprise positions.

4. Lateral Moves

I also spoke to a number of people who had built up a successful engineering organization but who then made a lateral move to anything from COO to running a customer success organization. Sometimes it was a strategic move, but more often it was in response to the needs of the business. Most found it interesting to take their experiences of building an engineering team and to apply it to other domains, but a number talked about their concerns of “diluting” their career — one who had been a successful COO found it quite hard to get back to the engineering side of the house when they were looking for their next role, despite being highly technical.

5. Consulting

A common theme was that of becoming a consultant or a “fractional CTO”. For most engineering leaders it’s an “in-between” strategy to test the waters with a number of teams, broaden their experience and keep their options open while also extending their runway so they can wait for just the right full time opportunity.

That said, some also find it a great lifestyle business, being able to impact a range of companies without having to fully engage with any of them. Generally the most successful consultants were those who priced assuming 50–70% utilization (you need 1–2 days a week for business development, running the business and generally fitting in tasks that are hard to bill a client for) and were good at and committed to the sales activities required to build a pipeline of clients.

6. The Entrepreneurial Itch

A common pattern was a CTO building a team, having a modest exit and then founding something else — either their own idea or joining a very early stage business so they could be a substantial owner in their next endeavor. Most people taking that route found it exhilarating (if exhausting), but the biggest downside was that the vast majority of the new ventures failed (or even worse, turned into zombies with anaemic growth and limited impact).

7. Putting on a Show

With a combination of communication skills and technical chops, I spoke to a couple of engineering leaders who had jumped across to developer relations — whether as senior advocates or to build a team. It’s a way to build an organization with technical staff and to focus on an entirely different set of challenges while still having a substantial impact on a growing business. The happiest seemed to be those working for successful B2D companies that were growing quickly and had interesting challenges in terms of building out customer success, training and customer feedback operations.

8. Back to the Coal Face

Something that many engineering leaders consider is taking a role as a hands on technologist. For those that still have (or can acquire) the skills, it can be a great change of pace. We all work hard to create organizations that allow our individual contributors to be focused, motivated, happy and successful, and it’s the rare engineering leader who doesn’t at least occasionally consider what it’d be like to work on a team instead of having to build and protect one!

It provides an opportunity to get back to a maker rather than a manager schedule and to be primarily working on tractable problems at a sustainable pace — something that isn’t always practical for engineering leaders — especially at startups). The downside is that you’re back to working on a much smaller part of a bigger picture, limiting your ability to impact the overall org, and generally it works best when you choose to work for an engineering leader you respect so that they can focus on building the team and you can focus on building the software.

What’s Your Journey?

In 2019 I’ll be publishing a series of articles about engineering leaders and their careers. If you’ve got an interesting career path and you’d like to contribute your story, please drop me a line!