Today, after more than 13 years at the company, I am joining Cloudflare’s board of directors and retiring from my full-time position as CTO.
Back in 2012 I wrote a short post on my personal site simply titled: Programmer. The post announced that I’d recently joined a company called CloudFlare (still sporting that capital “F”) with the job title Programmer. I’d chosen that title in part because it was the very first title I’d ever had, and because it would reflect what I’d be doing at Cloudflare.
I had spent a lot of time working at startups—in technical and then management roles—and wanted to go back to the really technical part that I loved most. Cloudflare gave me that opportunity, and I worked on a lot of systems that make up the Cloudflare that so many people around the world use today.
Looking back on my time at the company it’s really, really hard to pick my top highlights. In 2019 I wrote 6,000 words on the experience of helping build Cloudflare. But here are five that stand out:
The night we finished the preparation to launch Universal SSL sticks in my memory. We set out to offer the Industry's First Universal SSL for free, effectively doubling the size of the encrypted web overnight, a big deal in 2014. I remember Cloudflare’s third co-founder, Lee Holloway, hunched over his laptop finishing the code. The team has been working on it all weekend, and late that Sunday night Lee announced “it’s done.”
It’s easy to pick moments of great success or when things went really well and Cloudbleed in 2017 may not seem like a special moment, but it helped show who we were. It showed how a team could come together under intense stress, and how we could set the standard going forward for how companies disclose and talk about security problems. I personally discovered that a Google Meet call can be kept running for 24 hours and sleeping in two hour chunks is possible.
Being international and intentional
Originally from the UK, I was the first team member located outside the United States. I got to help build the largest offices outside the US: first, Cloudflare’s London office and then Cloudflare’s Lisbon office. These two offices are a big part of who we are today, with Lisbon being our European HQ.
When COVID halted our in-office work, I was blown away by the response from the team. As we all individually faced different difficulties because of the pandemic we continued to work together to ensure that the Internet, on which everyone was relying while confined at home, worked reliably and securely.
Truly impactful technology
Picking a favourite product would be a bit like asking someone to choose their favourite child, but I have soft spots for Cloudflare’s WAF, DNS, and DDoS solutions because I personally worked on those systems. And I still feel I need to apologize to the WAF team who took over my code and had to face that one Perl script that shall not be named!
Beyond the products there’s something much deeper: Cloudflare’s mission to help build a better Internet. I’ve been very proud of how we have supported and advanced the Internet itself through our work on the latest standards and protocols. And I’m even prouder of the role we’ve played through Project Galileo, The Athenian Project, and Cloudflare for Campaigns.
Every week Cloudflare holds an all-hands company meeting which ends with “Shoutouts,” a chance to recognize members of the team who have gone above and beyond. Curiosity and empathy are two core values at Cloudflare, and I am struck every week by how often we’re recognizing teams of people who are being thanked for helping with a sale, fixing a bug, responding to an incident, or helping build Cloudflare. That team spirit is part of what makes Cloudflare a special place to work.
One of the things I will miss about not being at Cloudflare day-to-day is the incredible strength of the individual team members. I’ve been learning from them for 13 years straight!
When I joined the company the team was a lot smaller! We were 25 people and now, we’ve grown to more than 4,200 employees and 15 locations across the globe. As we grew I wore a lot of different hats. For a time I ran engineering, operations, security, and even IT. And, of course, I wrote for, and edited, the Cloudflare Blog for many, many years. Over time, we hired many great leaders to run those teams.
But the role that persisted was CTO. And today, we are announcing that, just as I gave up the title Programmer (and the programming that went along with it), I am giving up the title CTO (and the role’s responsibilities) for a new way to help Cloudflare grow and succeed, as a member of the board of directors.
Last year when I told Matthew that I planned to retire, I had not expected to be offered a seat on the company’s board. It’s an incredible and rare honour to go from being an employee of the company (albeit one who has been there from close to the beginning) to joining the board of directors. I am absolutely thrilled to be able to continue helping Cloudflare grow and succeed from a slightly different vantage point.
At the same time, Dane Knecht, who, until today, was SVP of Emerging Technology and Incubation, has become our CTO. Dane joined just a few months after me, and is uniquely positioned and experienced to take the CTO role. We’ve worked so closely for the last 13 years as peers, that in many meetings it would’ve been hard to distinguish our roles. I’m pretty sure that Dane bleeds Cloudflare orange, and I’ve never seen him wear a T-shirt that doesn’t say Cloudflare on it. He has been part of nearly every major milestone here at Cloudflare. He cares so deeply about the company, and its success; he will make a great CTO.
My plan isn’t to go off and work somewhere else, or start a new company. I intend to remain closely involved with Cloudflare in my role on the board. I am incredibly honoured, and grateful to have been part of Cloudflare’s incredible growth and success, and I am looking forward to helping the company continue its growth.
One area I’m particularly interested in assisting with is the company’s work across the product suite on AI. Back in 2002 (23 years ago! gulp!). I wrote a very popular open source machine learning (didn’t call it AI back then) email filtering program and in 2004 worked on how to deal with what happens when one AI system is used to attack another. At Cloudflare, we’ve used learning techniques to enhance security, block bots, and predict how our systems should behave and grow. There’s much more to do.
Just as co-founder Michelle likes to say: we’re just getting started. And so am I.