CTOs: They're Just Like Us!

Chief Technology Officers. They’ve battled their way through the country’s finest institutions, put in their time at companies large and small, spent countless hours writing code to fix the old and usher in the new, and rose through the engineering ranks to this place. The Mecca of the engineering world.


So when we recently held a dinner for the leading CTOs in New York City, featuring John Allspaw, founder of IT consultancy Adaptive Capacity Labs and former CTO of Etsy, we couldn’t wait to hear their thoughts on DevOps, containers, edge computing, serverless and other buzzy engineering topics. After all, John has been leading software and systems engineering teams for over 20 years, and he’s spent the last 10 years researching human factors and cognitive systems engineering. He’s certainly a guy from whom everyone can learn a thing or two.

Turns out, though, the 15 CTOs gathered around the table - from companies including Betterment, BounceX, Greenhouse.io, Peloton and Rent the Runway - didn’t want to talk tech, per se. Instead, they spent hours (five, to be exact) picking each other’s brains about the softer side of the CTO role. They wanted to explore the human side of it all: what it means to be a good manager, what it takes to build great teams of motivated and empowered employees, how to feel fulfilled in a role that often feels more isolating than they had anticipated.

So what exactly is keeping this group up at night? No matter the industry, size of company or tenure, here are the most pressing issues these CTOs are thinking about:


This issue is of utmost importance to these guys right now (and we do mean guys; a number of attendees noted that Primary’s representatives were the only females in the room!). The subject came up almost immediately at our dinner. The group is extremely uncomfortable with the lack of diversity in the engineering community, and they’re desperate to find ways of changing that. But where to start? “It starts in a company’s culture,” one attendee remarked. “You need to take a hard look at your policies and ask yourself if they’re inclusive enough. How can you remove any inkling of bias from your interview process? How can you encourage more women to apply without giving the impression that you’ve lowered the bar?” And then, of course, the question of how to get more women into management roles, which the group ultimately agreed comes down to women seeing other female role models in leadership positions within their company.


Over the last 10 years, as mobility, cloud computing and co-working spaces have made remote work a more tangible and welcome reality for many companies, managers must grapple with how to lead and motivate teams from afar. But a remote workforce isn’t for everyone, and as the rock of the tech organization, it’s up to the CTO to determine what will work best for his/her employees, what will drive product development, and what arrangement will contribute to the overall success of the company.


Not every CTO is a natural manager, but figuring out long-term employee engagement and development is really the heart of the job. Perhaps the most difficult part of this, John said, is developing upward mobility within your team and training your staff on how to be good managers. His best advice here? “You can’t teach your kid to walk at the top of the stairs.” You start out by gradually increasing your employees’ responsibilities, being careful not to give them too much at once so that they are destined for failure. By getting certain members of your team comfortable with taking on more responsibility and larger roles, you will build clear career progression within your organization, and a path toward upward mobility for your staff.


“There are no best practices for how to turn into a CTO,” John said, and coming from the highly meditative programming role, it can be an incredibly difficult transition for many. John acknowledged that this was one of the hardest parts for him when he took over the CTO seat at Etsy. He missed his days as an individual contributor, and admitted to being a bit jealous of his team. As a programmer, you get so used to shipping code and getting that dopamine rush of pushing things live and immediately seeing a difference. But as a manager, you have to shift your mindset to a different kind of exhilaration. It’s important, John explains, to view your team’s wins as your own, and to take satisfaction in managerial accomplishments, such as shepherding your team to milestone achievements and driving innovation for your company.


Perhaps more than anything, last week’s dinner highlighted the need to support our CTOs. We so often think of this group as expert engineers (which they are, of course!), forgetting that in order for them to do their job well, they also need to master the human, team-building side of the business. These are the things that are often best learned by networking with a community of like-minded peers. We at Primary are thrilled to be able to facilitate such gatherings, where these CTOs can safely articulate, brainstorm, commiserate and learn from one another.

Thank you, John, for pulling back the curtain on the CTO role, and for encouraging such an open and honest dialogue amongst this group of talented CTOs.