Robert Entwistle

The path here was not a straight line.

I started in mechanical engineering at UCLA and Toyota, then moved into software as the web was taking off. I co-founded a technology company that grew from two people to twenty.

A disagreement about the company's direction eventually led to my departure. It was an early lesson that stayed with me: making good technology decisions requires more than understanding the technology. You also need to understand the business and bring people along.

From engineering to business

After leaving the company I co-founded, I worked independently with clients, building tire fitment tools, Windows desktop applications, and websites. I enjoyed solving technical problems, but I began to realize that understanding the business behind those problems was just as important as writing the software.

That led me to Europe and an MBA at INSEAD. I wanted to develop the business and financial judgment to complement my engineering background, particularly when evaluating investments, working with customers, and deciding what was worth building.

Enterprise technology and Apple

I joined BigMachines, later acquired by Oracle, managing enterprise SaaS implementations and helping recover projects that had fallen behind. The role combined technical problem-solving with customer relationships and delivery responsibility.

I then moved to Apple, working across business and technical teams in Europe and Cupertino. My work included developing a systems consolidation proposal for executive leadership, building an internal website for Education sales teams, and analyzing database performance for telecom reporting.

I eventually decided to return to London rather than relocate permanently to California.

Leading technology and engineering

At Mobilize, I became Head of Technology for a loyalty SaaS business. I was responsible for technical direction, architecture, and engineering delivery, while working directly with customers and leadership on product decisions. I led the migration to AWS and development of a customer self-service portal.

I subsequently joined dPivot, a data and media SaaS startup, where I again took responsibility for technology direction. I led the consolidation of eight legacy systems into one multi-tenant platform, modernized the application architecture, and developed data and reporting capabilities. The work combined architectural decisions, hands-on engineering, and understanding what clients actually needed.

These were the roles where I found the strongest fit: owning technical decisions while remaining close enough to implementation to understand the consequences.

Hands-on engineering and AI

After returning to Florida, I joined Harbor Compliance in a hands-on engineering position with an anticipated path toward broader technical leadership. I worked on database performance, cloud migration, integrations, and application security. Following a management change, the progression we had discussed was no longer available.

I returned to independent consulting, taking on SaaS architecture, performance optimization, and application modernization projects. I also invested time in applied AI, building four serverless prototypes using AWS Bedrock to explore document analysis, image assessment, contract review, and customer feedback.

One recent modernization project had been estimated at approximately six months. I completed the work in under six weeks. It reinforced something I have seen throughout my career: good architecture, clear priorities, and the right tools can make an enormous difference to delivery.

What I am looking for now

I am looking for a full-time role where I can take meaningful ownership of technology direction, architecture, and engineering delivery. I enjoy working with customers and business leadership to understand the problem, evaluating the options, and guiding development through to a working solution.

I am comfortable being hands-on, but my greatest value is bringing technical experience and business judgment together to make good decisions about what to build and how to build it.

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