It Takes a Village To Become A CTO

Terminal Tech Talk Panelists Discuss Mentors and Feedback Exercises They’ve Used to Get Where They Are Today.

Terminal
Terminal Inputs
6 min readNov 26, 2018

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CTOs might be alone at the top of the technical leadership ladder, but the good ones aren’t shy about reaching out to others for advice.

Here’s something we all know, but forget to acknowledge from time to time Technical execution and operations are the foundation of every successful modern company. Period.

The bulk of the responsibility of managing these aspects of the business falls on the CTO. Yet, I bet you can’t name 5 CTOs nearly as quickly as you could name 10 CEOs. Don’t feel guilty about it — a lot of them don’t want to stand under the spotlight.

After several decades of refinement, the position of CTO is now pretty well defined. They are responsible for the company’s tech strategy, including everything from monitoring trends that could help the company to developing new opportunities to participating in management discussions. They are also asked to focus on research and development, and like any other C-level team member, they act as an evangelist for the company. It’s not a repetitive song full of power chords — it’s a complex opus.

(Left to right: Marcelo Cortes of Faire, Alex Millar of Bonfire, Mike Kirkup of Encircle)

What’s not so clear is the road one takes to become a CTO. Because each company leans on a CTO in different areas, there aren’t too many common/well-worn stories/paths that lead to the seat. Next month our Terminal Tech Talk in Kitchener will focus on what different paths to the seat look like, what it takes to get there, and finally, an insider’s perspective on the job once you do make it. Nobody understands what the role entails and how to get there better than our panelists: Alex Millar, Marcelo Cortes, and Mike Kirkup. Collectively, these three technical leaders bring decades of experience at companies like Google, Microsoft, IBM, Blackberry, Square, and most recently, as CTOs who helped scale startups from scratch. Although each of their stories is unique, there is one commonality that emerges for successful leaders — they didn’t get there on their own. Everyone seeks mentorship and guidance on their way to a C-level position. Why? Because we can learn from the successes and failures of others almost as well as we can from our own. Learning by doing is important, but anyone who is able to learn by listening and watching others will get to their desired destination much faster.

In preparation for their upcoming Tech Talk, we asked our panel members a few questions about those who mentored them as they made their way to the C-suite.

Ask any executive and they will tell you, informal meetings with mentors are vital to success.

Who is one mentor that you had on your journey to CTO and what’s something you have learned from him or her along the way?

Mike Kirkup — CTO of Encircle: I didn’t have a single mentor — I had too many to count. In fact, I don’t think it’s a single mentor for anyone. When I took the job at Encircle one of the things I did was create a CTO peer group with similar people at local tech companies where we would meet every two months. It has been very helpful! We have covered almost every topic that matters to a CTO from hiring to patents to scaling the team to culture.

Alex Millar — CTO of Bonfire: Funny enough, Marc Morin, who is the moderator for our Tech Talk. Marc has a wealth of experience as a CTO. He’s also an investor in Bonfire. Early on, there is so much to learn. The biggest takeaways from Marc were on the technical and process side for our business.

Marcelo Cortes — CTO of Faire: The CTO role is different at every company. I don’t think it is possible to have one mentor. I get advice from many people according to my current challenges. I also pay a lot of attention to how leaders in different roles operate. But there is one person I get a lot of advice from — Jesse Wilson. We meet often and we either have high-level discussions on how to handle the up and coming challenges or we spend time whiteboarding.

What’s a weekly or monthly ritual you do to make sure that you continue to learn from outside your company?

Mike: I spend a lot of time reading and one of my favorites is the First Round Review (https://firstround.com/review/) where they have amazing stories from a number of technical leaders.

Alex: There are a few, but one is I religiously follow the Getting Things Done (GTD) process, and revise it. GTD enables the learning and creative capacity via offloading memory to a different system.

Marcelo: The one thing I like to do is to step back and look at what we have already accomplished. I ask everyone at the company to do this as well. The day-to-day life of a startup is hard and intense. We have challenges to deal with all day long — it feels like everything is a priority. But, it is very energizing to forget the day-to-day work for second and think about the big picture. It is amazing to look at where we were 6 months or a year ago and see everything we have accomplished. Then I try to imagine where we will be 6 months or a year in the future and how to get there.

Who do you look to now to help validate some of the ideas you have for your company?

Mike: I have expanded the number of people I seek out for advice including a number of great contacts in the Bay Area who have been through multiple startups. Sean Byrnes (https://twitter.com/sbyrnes) and Marko Gargenta (https://twitter.com/markog) have been a great help over the past couple of years.

Alex: The most important group I learn from these days is our customers. You hear that a lot, but it’s true. You need to talk with and listen to your customers.

Marcelo: Initially, it was just my co-founders. We complement and balance each other very well and we are always bouncing ideas of each other. We talk on the phone or hangouts many times a day. Next, I usually reach out to people with domain knowledge that I already know, or I ask investors to connect me to people who have domain knowledge. As an example, when I was deciding whether we should build a React Native app, I got connected with the VP of Engineering at Airbnb since they were using React Native extensively at the time.

To read more about Mike, Marcelo, and Alex, visit our event page. Oh, and don’t forget to RSVP for the upcoming Tech Talk!

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