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.

I have done this across multiple PE-backed portfolios over more than two decades, through MacLaurin Group which I co-founded, as Operating Partner at New Harbor Capital, Principal at ParkerGale, running TechOps across a growing portfolio, and recently as CTO at HiBid, the world’s second largest auction platform behind eBay, where I led a complete reimagination of the core platform.

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.

On AI, I have done this end to end. That means gearing up development teams to work AI-first, embedding AI capabilities directly into the product for customers, and rolling it out across business operations so the whole organisation benefits, not just the engineers. I have also built MCP servers that give businesses fast, structured access to their own data and systems, 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.

I have also carried out deep technical due diligence 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.

I grew up in Scotland and graduated from the University of Paisley with an honours degree in Computer Science. I was the first UK Java Champion, a programme by Oracle/Sun recognising 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.

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 honours degree in Computer Science. I was the first UK Java Champion, a program by Oracle recognising 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. My latest book, Think Like a CTO, is available in English, Russian, and Japanese.

What I am looking for

I am open to CTO and operating partner roles within PE-backed businesses. I am not looking for volume. I take on engagements where I can go deep, where the problems are real, and where the leadership wants someone who will tell them the truth. If that sounds like your situation, I would like to hear from you.

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.

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.