Why I left Cloudflare

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 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, and managing 24/7 on-call by myself (in fact, I created the on-call rotation and most of the monitoring). It was invigorating but tough. Management knew we needed more staff, so the plan was to eventually hire a larger team with the timeline around late 2021 and into 2022. The company was at that time also talking about re-opening the office and doing a "return to office" mandate, which I was personally looking forward to.

Unfortunately, as the economic environment changed, this created pressure on many companies, especially tech firms, to cut costs. So the hiring budget we were promised never really materialized. Budget for US-based roles dried up. However, we had someone transfer from another part of the company who was thankfully in my area so we were able to work in the office together. We were also able to hire two engineers in Europe to work remotely. We had a strong team and this was enough to do preliminary work on the project and maintenance on the existing system, but not a full sized team. Our manager expected more budget for hiring to open up, but it never did.

A series of leadership changes followed. 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. All active project work was cancelled, and my manager was let go.

This was basically a layoff event for my team. The entire management structure was let go, except for the individual contributors. ICs were kept on staff and transferred to other teams, but for a month we had no idea what team we would end up on, and no manager to report to.

I found myself juggling projects for two different, unrelated teams. One was my new assignment, the other was my previous team, which now lacked a full-time manager.

Because of the contracting job market, I didn't feel I had any choice but to accept this situation, and personal circumstances made it an unusually bad time for me to lose income. I also had some hope that I would get to move on to a new team assignment, because I liked working at Cloudflare, and I didn't want to leave.

After six months I was still working on-call for two different teams, on-boarding to a new project, and also being assigned last-minute work on my old project, which was now cut down to only two engineers, including myself. Then there were some stressful events that led to me working even more hours, with no hope of the situation improving.

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 complete the assignments I was given. I often found myself thinking, "what is the plan here?" Management reassured me that change was coming, but after six months, and after talking it over with family and friends, I decided that this was an unsustainable situation, and it was not likely to change anytime soon. 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 locally based team for me to work with. My project was dead and all the work we had done for it would be deleted. The office remained 95% empty most days. Instead of taking on a role in a growing engineering team, my job became a solitary 24/7 on-call support role. I was also not allowed to move to a new project so a transfer was out of the question. I was working to onboard to my new team assignment, but I was still being pulled off to do hours of unplanned work for my previous team, yet I was still going to be evaluated based on my contributions to my new assignment, which I couldn't even focus on. It was all very confusing.

It was time to let go, and seek another path.

I am grateful for the experience. I'm professionally better off for my time at the company and 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 many future projects that I build. I have huge respect for my former colleagues. I am still interested in security, and I hope that I can find my way back to working on security projects in the future.