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.

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.

Picki