In 2018, I had just moved to Austin from Los Angeles. I had been working remotely for most of my career, and had moved from Simple (a fintech startup) to Product Hunt (another startup). After PH, I took what I thought would be a quick detour into professionally teaching developers.
I had been teaching developers at that point. After all, I was self-taught: I learned from Railscasts and the Rails Tutorial at the beginning of my career. A few years in, I had learned enough about a few things, like payments (using a very early version of Stripe), and tools like emmet. I reached out to Pluralsight, and started working together. A few months later, I released Getting Started with Payments on Ruby on Rails - my first course.
In early 2019, I started working on Byteconf, a series of virtual developer conferences hosted on Twitch. Many of the speakers I was working with, and often the people who were also connecting me to sponsors, had a job title I didn't know anything about: Developer Advocates.
I found that role really interesting because it played to what I perceived as two of my strengths: software development and teaching. As I continued to teach, I started to orient my search for my next full-time role towards Developer Advocacy.
And that paid off - later that year, I found a role at Cloudflare, joining as their first Developer Advocate on the Workers platform.
Seven years and three titles later, my time at Cloudflare has ended. Over that time, I moved into management - managing a few different iterations of our Developer Relations team (and going back to being an IC for a stretch, too).
It was great fun. I'm still incredibly bullish on Cloudflare's Developer Platform, and I deploy the apps I'm building post-Cloudflare on the platform. Not because I have free credits, or out of loyalty - I just like building on it. Workers is an incredibly compelling platform for deploying the kind of applications I'm building.
I'm really proud of the work I did. The definitive work I did as an IC was my Workers 101 video. As a manager, I worked with a bunch of iterations of Cloudflare's Developer Relations teams, doing my best to shepherd them through the role itself changing. And boy, did it change - I started during the heyday of devrel in the late 2010s, and watched it evolve into an oft-maligned, post-AI version of itself that, frankly speaking, is a lot less valuable than it used to be. But regardless: it was incredibly fun, I loved every iteration of my team, and I'm happy to call so many people I worked with there very close friends. That includes peers, people on my team, and so many other people. It was a huge part of my life here in Austin so far. 90% of the time I've spent in Austin has been while working at Cloudflare.
I'd like to take some more time to formally write up some of the things I've learned while I was at Cloudflare. One of my regrets is, at a really basic level, not doing this: journaling or writing down my thoughts during those 7.5 years. It's a lot easier to place yourself in the past if you have context. I had, if I remember correctly, five different managers while I was at Cloudflare. Half of them, I can barely remember their management style, what I was specifically working on during that time, and at a more basic level - was I having fun? Next time, I'll take better notes.
So what am I doing now?
In August of this year, I was casually looking for new jobs. Nothing serious, no real time pressure - I just had been at Cloudflare for a long time and I wanted to see what else was out there. I saw a role that had been posted just a few days before - Head of Product Education Engineering at Cursor. I applied, and began chatting with the team.
A few weeks later (very quickly - genuinely the quickest start-to-finish process of my career) I had an incredibly compelling offer to join SpaceXAI (their acquisition of Cursor finished during my interview process). The team is building educational and enablement content out for all of SpaceXAI's properties - Cursor, the XAI products (like the Grok models and all of the associated API products), and, my favorite - Grok Bot (more on that soon). It's a lot of the teaching and education work I enjoyed in Developer Relations, with less travel and less marketing. While I still think the best people doing devrel make it feel like it isn't marketing, the truth is that 80% of it does feel that way - it's promoting a product, even if it's genuine promotion - and I wanted a break from that.
Now I'm heads-down there, working on a backlog of content that I'm quite excited about. And, with a little less time needed thinking about marketing, about "advocacy". That excites me. I'm back to building stuff that I find interesting. I'm spending the winter not feeling the pull to post on X unless I want to. Just building stuff for the sake of building! It's great. Change is good.