From Programmer to Board Seat: A 13-Year Arc at Cloudflare

After more than 13 years at Cloudflare, I am stepping away from the full-time role of CTO to join the company's board of directors. It is the culmination of a career that began in 2012 with a deliberately simple job title: Programmer.

I chose that title intentionally. After years in technical and then management roles at startups, I wanted to return to the hands-on engineering work I loved most. Cloudflare offered that chance, and I spent my early years building the systems that millions now rely on daily.

Reflecting on a tenure that saw the company grow from 25 people to more than 4,200 employees across 15 global offices, a few moments define the experience.

Defining Moments

Shipping Universal SSL. The night we finalized the launch of Universal SSL remains vivid. Our goal was to offer free SSL encryption to every site on the internet, effectively doubling the size of the encrypted web overnight in 2014. I remember Cloudflare's third co-founder, Lee Holloway, hunched over his laptop finishing the code after a weekend of effort. Late Sunday night, he simply announced, "it's done."

Handling adversity. The Cloudbleed incident in 2017 was not a moment of triumph, but it demonstrated the team's character. Under intense pressure, we came together and set a new standard for how companies disclose and discuss security problems. That period taught me that a Google Meet call can run for 24 hours straight and that sleeping in two-hour increments is possible.

Building internationally. As a UK native, I was the first employee based outside the US. I helped establish our London office and then our Lisbon office, which remains our European headquarters. When COVID forced everyone home, the team's response was remarkable. Despite facing different personal hardships, we worked to keep the internet—which everyone now depended on—running reliably and securely.

Working on real technology. Choosing a favorite product is like choosing a favorite child. But I have a soft spot for Cloudflare's WAF, DNS, and DDoS solutions because I worked on them directly. I still owe an apology to the WAF team that inherited my code, including one Perl script that shall not be named. More broadly, I am proud of our work advancing internet standards and protocols, as well as initiatives like Project Galileo, The Athenian Project, and Cloudflare for Campaigns.

The people. Every week, our all-hands meeting ends with "Shoutouts," recognizing teams that go above and beyond. The consistent theme is collaboration: teams being thanked for helping with a sale, fixing a bug, or responding to an incident. That team spirit is what makes Cloudflare special, and I've been learning from my colleagues for 13 straight years.

Passing the Baton

As the company grew, I wore many hats—running engineering, operations, security, and IT at various times. Eventually, we hired strong leaders for each of those roles, but the CTO position persisted. Now, I am giving up that title and its responsibilities for a new perspective on the board.

Dane Knecht, who served as SVP of Emerging Technology and Incubation, has stepped into the CTO role. Dane joined just months after I did and has been part of nearly every major milestone here. We worked so closely as peers for 13 years that it was often hard to distinguish our roles in meetings. He deeply understands the company and its mission, and he will make an excellent CTO. I've never seen him wear a T-shirt that doesn't say Cloudflare on it.

My plan is not to leave and start something new. I intend to remain closely involved, particularly in the company's work on AI. This is familiar territory: in 2002 I wrote a popular open-source email filtering program called POPFile, and in 2004 I explored what happens when one AI system attacks another. At Cloudflare, we've already used learning techniques to enhance security, block bots, and predict system behavior. There is much more to do.

As our co-founder Michelle likes to say, we're just getting started. And so am I.