Alan Williamson

I do one thing: walk into businesses and make them work better. That has meant different things across different engagements, but the pattern is consistent. I go in, I learn what is actually broken, and I fix it. Not by pointing at a whiteboard and leaving, but by getting into the trenches and showing how it is done.

The Work

What follows is a sampling. The engagements have varied considerably, but these illustrate the range.

At one portfolio company I spent two years going back and forth to India, embedding myself inside a 100+ person engineering team that had lost its focus. Adding more people had been the answer to every problem, which had made everything worse. I got to know the team personally, because they were not rows in a spreadsheet. I elevated the people who could lead, invested in those who were teachable, and made the hard calls on those who were not the right fit. The team came out smaller, sharper, and actually delivering.

At another, I migrated an in-house EHR to a commercial solution, removing $1.2 million in annual costs and freeing the business to focus on what it was actually built to do.

Across multiple engagements I have taken businesses from on-premise to cloud-native, redesigning architectures to be properly scalable, serverless where it makes sense, and built to grow without the engineering team becoming the bottleneck.

AI Experience

On AI, I have done this end to end. I have built agentic AI workflows that generate production-ready code, stood up an AI image analysis pipeline that processes millions of images a day for identification, and led the build of a full ERP system powered largely by autonomous AI agents.

Beyond that, I built an AI image and video studio for product editing at e-commerce scale, a document AI pipeline that processes invoices and purchase orders for a financial services client, and an agent assistant for patient care in healthcare. Some of this runs on infrastructure the client controls rather than a vendor’s cloud. I have set up local LLM serving for sensitive data, and local model serving for text-to-speech generation agents.

Gearing up development teams matters as much as the technology. I ran AI enablement for two cohorts of 30 engineers, publishing the internal guidelines they now use for day-to-day delivery, then embedded AI capabilities directly into the product for customers and rolled it out across business operations so the whole organization benefits, not just the engineers.

On top of that, I built MCP servers that give businesses fast, structured access to their own data and systems, including a secure MCP server for data-warehouse access, across multiple clients including HiBid. That last piece matters because most businesses are sitting on information they cannot easily get to. MCP changes that quickly.

Diligence Experience

Due diligence is another piece of this. I carry out deep technical assessments for PE firms evaluating acquisitions. Good diligence does not just flag problems. It tells you whether those problems are fixable within your thesis, or whether the gap between what the technology is and what it needs to become is a reason to walk away.

The Bridge

I work well with boards and business leadership, which is rarer than it should be in technology executives. I have been told more than once that my particular skill is taking something genuinely complex and finding the right frame for it, the analogy that makes the decision clear to people who did not go to computer science school. In PE-backed businesses, the gap between the engineering room and the deal room can be expensive. I close that gap.

Background

I grew up in Scotland and graduated from the University of Paisley with an honors degree in Computer Science. I was the first UK Java Champion, a program by Oracle recognizing the top 100 contributors to the Java ecosystem globally. I have spoken at over 30 conferences worldwide, contributed to major open source projects, and built systems that have powered some of the largest sites on the internet.

I am also an author. My latest book, Think Like a CTO, is available in English, Russian, and Japanese. It is the distillation of everything I have learned sitting in that chair across more than two decades.

What I am looking for

If you run a PE-backed (or not) business and want AI that actually works in production, that is what ThinkLikeACTO.ai does. Ryan Burch and I take on AI readiness assessments, leadership foundations, dev team enablement, and product integration work. We are deliberately small and take on a limited number of engagements per quarter so we can do the work properly. If that sounds like your situation, talk to us at thinklikeacto.ai.

This site

I have been writing here since the early 2000s. It is where I think out loud, mostly about technology, occasionally about life, and sometimes about the uncomfortable overlap between the two.

Podcasts

I have popped up on many podcasts, pontificating on a wide range of topics that hits the desk of a CTO.

Alan enjoys wood turning when he is not at the keyboard (ask about the butt-plug-candle should you get the chance) and is a huge movie buff, with an uncanny ability to quote movie lines from many an obscure title. Had he not had a fondness for computing, he would have explored a degree in Cinema and Media.