Backfilling an executive as a Founder

Problem

When the company was five years old with about 150 employees, our Heads of Engineering, Product, and Design resigned together to start a new company. They gave us plenty of notice, but we had to act quickly to make the necessary changes.

Actions taken

The CEO and I stepped into the Head of Product and Head of Engineering roles, and we promoted a senior designer to Head of Design. We made sure to communicate the changes quickly, filling everyone in on what was going on and reassuring them that it wasn't the end of the world. I stayed in the role and interviewed professional candidates for about a year, eventually hiring a more seasoned executive.

Lessons learned

1. "Life goes on when an executive leaves." As we built our executive team over the first few years of the company, I always feared that even one premature departure from that team would be a major, possibly fatal setback. In our case, even with multiple simultaneous departures, the day-to-day product development work continued mostly uninterrupted. Other managers and engineers rose to the occasion, taking on more responsibility. Maintaining the status quo is easier than I had realized. The real challenge for (and expectation you should have of) an executive is to aggressively take their function to the next level.
2. "Be humble about your abilities." In retrospect, I stayed in the interim role longer than ideal. I felt like I was doing a decent job and improving, and therefore decided to take my time to find the perfect candidate. Having worked with the previous Head of Engineering closely, I felt like I had a strong handle of the role and was excited to put my own philosophy into practice. On the other hand, I didn't have a ton of hands-on experience. Some of the hardest parts of people management in a large organization — firing people, adjusting scope, and hiring people better than anyone on the team — are easy to see the value of but inherently painful or unnatural to execute, and simultaneously easy to delay taking action on. After hiring a professional, I also started to become aware of my blind spots — things that never came up when growing the engineering team from 0 to 50, but that are common in a team of over 50 people. For instance, I hadn't had a clear idea of what to expect from a "director"-level manager.
3. "Level yourself up by learning from candidates." Interviews with executive candidates double as a rare, cost-effective opportunity to learn. In the process of interviewing these candidates, I absorbed some of their wisdom and tricks of the trade, and then incorporated them into my work. While I think this was a net benefit, there is a danger of feeling more and more confident in your knowledge as you do more of these interviews (without the accompanying experiences that led to those insights), which tends to increase your bar for the hire — eventually to an impractical and unnecessary level.
4. "Spend some time learning the role, but don't undervalue speed of replacement." An executive hire, as with any other hiring decision, is a two-way door. If it doesn't work out, you can always try again — usually without any permanent damage. As a founder of a blitzscaling company, you don't have the luxury of spending years becoming a world-class expert in managing a specific function at a particular stage. Your goal is to keep getting the company to the next stage as quickly as possible. However, doing the job yourself for a little while is a good way to get a sense of what to look for in professional candidates to avoid making a terrible hire.
5. "Don't be dogmatic about promoting from within." There are many benefits of promoting from within, but there are also many benefits of bringing in a new leader. Which one is better completely depends on the situation. In our case, we were four years into the company and had already more-or-less exhausted our network for experienced engineering talent. By occupying the apex of the people manager hierarchy, I was imposing an artificial ceiling on the management talent that would be interested in joining in a non-executive capacity, since people, usually with the exception of executives themselves, prefer to report to someone more experienced. When we hired a professional Head of Engineering, he was able to, within a few months, hire a wave of more experienced managers and engineers than had existed on the team. In general, someone with decades of management experience is at a huge advantage in hiring from his/her network compared to someone who hasn't even been out of college for a decade.