The Five Flavors of Being a CTO

Perhaps you’re the co-founder and CTO of a company that’s made it through your series-A funding round. It’s been a crazy journey so far — you coded and shipped the initial product, then convinced early employees, investors and customers of your company’s vision and future. Now the team is starting to scale and you’re bringing on people that have “done this before”. Congrats: you’ve made it further than many other startups. On the other hand, you’re likely facing the existential question: what the hell is a Chief Technology Officer actually supposed to do?

There is, quite simply, no other C-level title as variously-defined as “CTO”. Are you the person that shapes the product architecture? That espouses a technology vision to the world? That manages the engineering team? All of the above? Without a clear role and success criteria, you’ll accomplish less by spreading yourself all over the place.

Over the 15 years that I was CTO and took my company from bootstrapped startup to being public, I grappled with the role myself and passed-on what learnings I could to other entrepreneurs. I’ve seen many failures along the way — founder/CTOs that quit in frustration. It doesn’t have to be that way. Being a “CTO/Co-Founder” can in fact be an incredibly fulfilling and long-term gig.

Alright, so what exactly is the CTO role? I find it useful to break it into five flavors, split between an external and internal focus:

External

  • Evangelist: you’re the key spokesperson in promoting a technology vision to the world. You speak at conferences, talk to press, and have myriad social media followers. If your company has an Open Source community, you’re the leader; same story if your company participates in open standards.
  • Super Sales Engineer: you’re the ultimate weapon in winning over new customers: able to talk about your company’s products, technology and roadmap with a depth and vision that nobody else can match. You live to win and can light up a room.


Internal

  • Super Engineer: you’re a prolific and accomplished coder. You define the architecture and lead innovation by example. Every time you step up to a whiteboard, the team gets inspired by what you imagine and accomplish together.
  • People Leader: you manage the engineering team, and in special cases the product and design teams as well. You’re constantly recruiting new talent and mentoring existing employees. You’re focused on shipping great product, and manage the team to quality and velocity metrics. You’re either performing the VP of Engineering role yourself, or that person reports to you.
  • Innovator/Disruptor: you’re constantly on the hunt for the “next big thing”, whether it’s a new technology or a new product. You live to disrupt the industry and your existing business, and you accomplish it all with a talented but small team. 


If you were hired as CTO, your job should be fairly tightly defined as one of the above flavors or perhaps a combo. It’s when you’re a co-founder with the CTO title that things can get a bit more confusing. You probably start off as a Super Engineer, simply building as much and as fast as you can. Next, somebody needs to manage the engineers you’re hiring, so you start having sporadic 1-on-1s and lead a daily standup. As the company keeps scaling, perhaps you’re increasingly pulled into customer meetings and to speaking at tech conferences. This continues and iterates until one day you wake up and realize you’re dropping the ball on all of it and feeling miserable with all the context switching. Maybe your CEO has kicked off one of the slightly awkward “let’s talk about what’s next for you and how to make you more successful” conversations (I’ve had a few of those, for the record). So now what?  

To reset your role into something that makes more sense, I suggest the following:

  1. Use the five flavors as a framework for discussing with your CEO and the rest of the exec team what your role should encompass. 
  2. Be honest with yourself about your existing skills, what you are most passionate about learning next, and most importantly what the company needs from you.
  3. Agree to an internal vs. external balance for your version of CTO. It’s challenging to mix the two and they require very different skills, so it’s important to be clear. I even talked to TechCrunch about this topic.
  4. Make your role changes proactively vs. waiting until things break or until you’re miserable by re-assessing every two years.
  5. Ask for feedback, both inside your company as well as from other CTOs.


Perhaps all of this sounds frustrating and still a bit un-clear. The counter-point is that being “the CTO” provides an enormous amount of freedom to chart your own course while at the same time having massive positive impact on your company. As for myself: I recently hung up the CTO hat that I’ve been wearing for so long in order to begin my next startup. Good luck in your own journey

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