Why I left Cloudflare

In 2017 I moved to Austin seeking more work opportunities. I felt I was outgrowing the employment options available to me as a software developer in my home metro area. The Austin area was a booming job market, so there was a lot more opportunity there for me.

Soon after making this move, I started to become really fascinated by security. During some downtime between projects, I took the Stanford course on cryptography, and this really sealed my belief that security was the place I was meant to be. It combined my technical interests with a mission to do good by protecting the world from criminals and hostile nation-states.

I started looking for an opportunity to enter the security space, but after a layoff, the pandemic hit, and it seemed unlikely I would find that opportunity. I considered putting any professional aspirations on hold until the world settled down a bit. But after a trip home to visit with family, I decided that "moving forward" was the only option. I decided Austin was a better place to find a job working in security, privacy, and related fields. My dream was to contribute to security systems using my backend engineering background as a starting point.

Then I was fortunate to have the security team at Cloudflare reach out to me in late 2020. This was at the height of the pandemic. I interviewed in November and December 2020, and accepted the offer the following January.

I started at Cloudflare with great enthusiasm. I had never worked on a project that had such impact. Most of my roles had been in smaller startup type companies. Suddenly I was managing a system that was processing a huge influx of data and where uptime really mattered. It was a great engineering challenge. I inherited a system built for much smaller volume, and had to quickly plot a course to scaling it up. I was working 10-12 hours a day most days. The plan was to eventually then hire a team that I would lead, with the timeline being around September 2021. The company was at that time also talking about re-opening the office and doing a "return to office" mandate in September 2021. If this had taken place, I would have become a senior or lead engineer on a very impactful security project working with a team of new hires in Austin – a full team building a next generation security system. I started dreaming of establishing a permanent home in Austin. I even bought furniture and gardening supplies anticipating this. I was excited and working hard to make it reality, saving money aggressively, and decking my small apartment out to resemble a proper home.

Unfortunately, as the economic environment changed, this created pressure on many companies, especially tech firms, to cut costs. So the hiring budget never really materialized. A colleague joined from another part of the company, and we were able to hire two very talented engineers in Europe to work remotely. We began some preliminary work on the project, but doing this while maintaining the legacy system was too big of a task for a small team, with a large backlog of requirements to work through. Our manager expected more budget for hiring to open up, but it never did.

A series of major leadership changes were to follow. In summer of 2023, the group was "reorganized" and all the teams that were building software within the security org were reassigned to different roles in the company. Management was let go unceremoniously. All active project work was cancelled.

After this event I was somehow responsible for two different teams. One was a new assignment. The other was my previous project, which now lacked a full-time manager, as our manager had been fired.

Now I was working on-call for two different teams, on-boarding to a new project, and also being assigned last-minute work on the supposedly cancelled project. It felt like leadership didn't really have a plan for me.

Because of the contracting job market, I didn't feel I had any choice but to accept this situation. I had a particularly dark couple of weeks in late 2023. I was not sleeping, and I felt my health declining. My life outside work was seriously affected. I tried to keep a professional demeanor and positive attitude and to support the assignments I was given.

After talking it over with family and friends, I decided that this was an unsustainable situation, and it was not likely to change in the short-term. I resigned in January 2024.

I was with the company for almost three years. The promises when I first joined were just not working out. There was no team in Austin for me to lead, that was never going to happen. In fact, the office in Austin remained 95% empty most days. Instead of taking on an important role in a growing engineering team, my job became a solitary 24/7 on-call support role. Most of my former colleagues went off to new projects and roles. I was ready to move on myself, but the company would not let me. I was still being pulled off to do unplanned work for my dissolved team.

At this point my motivation started to fail. I was working very hard to succeed in my job, make it to that next stock vesting date, and save more money. With housing prices increasing faster than I can earn, I was running on the proverbial hamster wheel. My dream of having a permanent home and an important role in an engineering team in Austin became more like a delusional fantasy than a realistic goal. It was time to let go, and seek another path.

I am honestly very grateful for the experience. I had a dream of working on security projects in a high caliber company, and for almost three years I got to do it. It didn't pan out as I would have hoped, but it was still an overall positive experience. I'm still professionally better off for my time at the company.

I still think Cloudflare is an incredible company. I use Cloudflare every day to secure my own home network, run my personal website, and manage my domains. I plan to use Cloudflare for future projects that I build. I have huge respect for my former colleagues at Cloudflare. I am still interested in security, and I hope that I can find my way back to working on security projects in the future.