When to hire a head of engineering and what to look for

Mathilde Collin
Sep 6, 2018 · 3 min read

There comes a time in every startup’s journey when it becomes clear that engineering needs a dedicated leader. As is the case in most startups, my co-founder Laurent Perrin initially played the role of both CTO and head of engineering. But as the demands of being lead architect (his CTO responsibilities) became ever more important to scaling the business, we decided the time had come to bring in an experienced engineering leader who could manage the existing team, build the future team, implement the right processes, and so forth.

That’s why earlier this year, Shane Lowry joined Front as our Head of Engineering. With 20 years of experience in engineering leadership, Shane has the technical and management skills required to grow our complex, geographically distributed cloud service. More importantly, he brings a humble, collaborative, and creative approach to engineering that Laurent and I felt was critical to this role.

Because I know many founders struggle with when to bring in a head of engineering, I thought I’d share some insights into how Laurent and I approached this decision and the attributes we prioritized in our search.

When to hire a head of engineering

Here are some of the things we began to notice that made it clear we needed a dedicated head of engineering at Front:

  • Product lacked a single point of contact in engineering so individual engineering contributors were wasting time on process and prioritization tasks.
  • Engineers were questioning their career paths and a few were looking for new opportunities where they could make an impact without contributing code directly.
  • Coordinating work across our growing team of engineers was getting increasingly difficult.
  • A few engineers who have been with the company the longest were the only experts of the lion’s share of the core components and as a result, these usual suspects were the ones pulled into escalations and were at risk for burn out.
  • I was spending too much of my time interviewing and selling engineering candidates on Front.

What to look for

The CTO role differs a lot from company to company. Some CTOs stop coding quickly. Others want to remain in charge of key technical decisions, while not contributing to day-to-day code. Before beginning a head of engineering search, it’s important to understand the scope of your CTO’s role to ensure very little overlap between the two positions.

Regardless of where the lines are drawn, here is a short list of attributes I think all founders should look for in their first head of engineering:

  1. Is adaptable, not looking to replicate another company’s culture. An ideal head of engineering respects engineering process but isn’t pedantic about it. He or she understands engineers and teams and can come up with organic solutions for how to make them happier, more efficient, and more effective.
  2. Commands respect without actually commanding. A respected leader can galvanize an engineering team around delivering a release / product, even when it requires putting in extra time to do so. Everyone says they know how to do this, but be sure to ask for examples and when you hear them, make sure you would want to work for that person too. In general, respect is something that is very hard to assess in a few conversations or interviews so references from trusted sources are key.
  3. Understands how to interview, sell, and hire engineers. This is something else that everyone says they can do, but is actually quite rare to find. It’s even more rare if someone understands how to do this at various levels of maturity for a company.
  4. Sees both short and long term opportunities. Your head of engineering should be able to form solid arguments for both building something quickly to get it out there and building something a bit more slowly to increase stability, reduce bugs, handle more load, etc. There are pros and cons to both and it’s important that your engineering leader is able to understand when one or the other is most appropriate.
  5. Has humility. A solid head of engineering is humble about their own contributions and celebrates the accomplishments of the team. I’m wary of candidates that use too many “I” statements when results were clearly thanks to a team effort. Furthermore, a head of engineering’s humility should extend to both what your team has already accomplished as well as the challenges you have in front of you.

Mathilde Collin

Written by

LEGO builder. Co-founder & CEO @ Front (frontapp.com)

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