Robert Entwistle

The path here was not a straight line.

I studied Mechanical Engineering at UCLA and started at Toyota as a forklift engineer. I left to co-found a company as the web was taking off. We grew it from 2 people to 20.

I was outvoted and pushed out over a disagreement about where the company should go. It was a hard way to learn that being right about the product is not the same as having the votes.

Client work, then business school

After I left the company, I did contracting work building tire fitment finders, Windows desktop software, and client websites. I was working directly with clients but still making decisions through a purely technical lens. I moved to Europe for an INSEAD MBA to build the business framework that matched the client instincts I had already developed.

Enterprise software, then Apple

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

When Apple later asked the team to relocate to the new campus, I chose to leave rather than move back to California.

Back to hands-on leadership

I became Head of Technology at Mobilize, leading an AWS migration and the iOS work. When new investors brought in their own leadership team, the role ended.

From there I joined dPivot, a small startup, where I worked directly with clients to turn their problems into projects and proposals, managed budgets, and stayed hands-on through the build. That included converting a legacy CodeIgniter platform to Laravel and building out the image management and data systems.

A step back, then a deliberate pause

After moving back to Florida, I took a remote role at Harbor Compliance. The level of ownership I expected never fully materialized, and the company’s restrictions around AI made it hard to work the way I work best. I left.

I took six months to go deep on AI. I rebuilt four tools based on real problems I had previously solved by hand: compliance research, image quality review, contract analysis, and feedback triage. During that time I also did contract work implementing roadmap items for a previous company, including updating an aging frontend. The work had been quoted at around six months. I delivered it in under six weeks.

What I am looking for now

I am looking for a full-time role with real ownership over a problem, not a queue of tickets. Across every role, the ones that went well and the ones that did not, the pattern is the same: I do my best work when I am trusted with an open problem and the room to take it from idea to shipped system.

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