The path here was not a straight line.

After the company ended, I did contracting work, building tire fitment finders, Windows desktop software with databases, and client websites. I was working directly with clients but making decisions with a purely technical lens. I moved to Europe to get an INSEAD MBA, which gave me the business vocabulary and framework to match the client instincts I had already been building on the job.

I joined BigMachines, later acquired by Oracle, working on Salesforce integrations for their quoting platform. That work led to a recruitment into Apple as a CRM Manager, where I built proof of concepts for the education and telecom units.

Steve Jobs died while I was there. Not long after, Apple finished its new campus and asked our team to relocate. I am from California originally, and did not want to move back, so I chose to leave and take on a different kind of role instead.

I became Head of Technology at Mobilize, leading an AWS migration and the iOS app work. When new investors came in, they brought their own leadership team, and my role along with it came to an end.

From there I joined dPivot, a small startup, where I worked directly with clients to translate their problems into projects and proposals, managed budgets, and then built the work myself or with a small team, including converting their legacy CodeIgniter platform to Laravel and building out image management and data systems in SQL. It was the clearest version yet of the pattern I keep coming back to: sitting between the client's problem and the delivered system, and staying hands-on through both.

After getting married, my wife, son, and I moved from the UK to Florida. I chose Harbor Compliance over another offer because it was remote, with the understanding that my level would catch up quickly once I proved myself. It didn't move as fast as expected, and the role eventually narrowed into ticket work rather than the ownership I'd been promised. The company was also, understandably, strict about AI usage given its work in government compliance, which meant I could not bring in the kind of AI-assisted workflow I was already itching to use. I left rather than stay in a role that was not using what I actually do best.

I took six months off after that, on purpose, to go deep on AI. I rebuilt four tools based on real problems I had solved before by hand: compliance research, image quality review, contract analysis, and feedback triage, to see how AI could handle work that used to take a person hours. I also put what I was learning to the test on a former colleague's platform, rebuilding their legacy Bootstrap frontend in PrimeReact, wrapped in my own custom components rather than used directly. Good thing too: PrimeReact changed its licensing right after I finished, and that wrapper let me migrate the whole thing to Mantine without a rewrite. Quoted at around 6 months of work, I delivered both versions in under 6 weeks.