Scaling from Startup CTO and Entertaining the Idea of Hiring a VP of Engineering

Problem

The CTO role can mean a very broad set of responsibilities inside many organizations (managing engineers, setting a technical vision, working with customers, etc). Staying on top of it all and shifting your area of focus over time is challenging. In particular, as the company scales, there's a specific responsibility that can take huge amounts of focus and energy: performing the day to day management of the engineering organization. Attacking management problems is quite different than attacking engineering/technical problems and you may find yourself asking whether it's time to hire a VP of Engineering to take over the team, particularly if you're a co-founder/CTO and have never managed large teams before.

"Staying on top of it all and shifting your area of focus over time is challenging."

If you are looking to hire a VP of Engineering, there are some challenging questions without obvious answers for you and the rest of the executive team! In particular, should the VP of Engineering report to you as the CTO, should you be peers, or should you report to the newly hired VP of Engineering? While there are pros and cons to each option, one scenario I consider a bit of an anti-pattern is the notion that a CTO can have a VP of Engineering report to them and "handle all the people stuff" while they're off focusing on other parts of the business. This adds a layer of indirection to the problem that under-optimizes for everyone.

Actions taken

• I might consider being a peer to the VP of engineering if being "CTO" at the company means dividing my time between many different challenges: product work, pushing forward the architecture and technical vision, selling to prospects and working with customers, etc. The VP of Engineering would report to the CEO and would have the entire engineering team report to them. I might have one or more small teams reporting to me focused around specific areas of responsibility that I own.
• I might consider having a VP of Engineering report to me if I already have considerable experience managing large teams, but my responsibilities supersede just engineering management. In this scenario, I'd remain very deeply engaged in the management of the engineering team, as it will likely be the most challenging and important aspect of organization responsibilities I ultimately own.
• I might report to a new VP of Engineering especially if I'm a co-founder of the company and haven't managed people in my career previously. I'd find a VP of Engineering that I'm truly inspired to work for and that can provide significant mentorship. This scenario might also free me to focus deeply on technical work and not having to worry about people management.
• Finally, instead of hiring a VP of Engineering, I might take a baby step first in figuring out how to deal with a growing team by hiring the first set of dedicated engineering managers.

Lessons learned

• Start by asking the question: "what's truly best for the company?", and don't get trapped by your ego as you make decisions around reporting structure.
• You may be doing this for the first time, this is a really hard problem that you're going to need significant help with (everyone does!). Consider an executive coach or find other mentors. Don't wait and resist change when you know it needs to be done.