Alan Williamson

Background

About Alan Williamson

I am a Chief Technology Officer with nearly thirty years of experience building, modernizing, and scaling technology platforms, with deep experience in private equity backed environments where speed, clarity, and execution matter.I currently serve as CTO of HiBid, one of the largest online auction marketplaces in North America. I lead platform strategy, system architecture, and engineering execution, with a focus on scaling a high volume, transaction heavy marketplace while modernizing a legacy technology foundation.A core theme of my career is legacy modernization. I specialize in transforming tightly coupled, aging systems into cloud native, API driven, microservices based platforms that scale reliably and evolve without friction. I have led multiple large scale rearchitecture efforts across PE backed companies, turning technology from a bottleneck into a growth engine.Prior to HiBid, I was a Partner at New Harbor Capital where I led technology strategy across the portfolio. I have held CTO and interim CTO roles at companies including Royall and Company, and supported private equity firms such as Chicago Growth Partners and ParkerGale Capital through MacLaurin Group. My work has consistently focused on platform rebuilds, cloud migrations, cost reduction, and building effective onshore and offshore engineering organizations.My background is deeply technical when required, from reverse engineering embedded firmware in IoT turnarounds to designing large scale distributed systems. Earlier in my career I was named the first Java Champion in the UK, an award granted by the developer community. I am also the author of multiple technical books, including Think Like a CTO, a practical guide for technology leaders.A significant part of my current work involves applied artificial intelligence. I work hands on with public and private models, including AWS Bedrock and SageMaker. I design and build agents, experiment with retrieval strategies, and apply AI where it delivers measurable business impact rather than experimentation for its own sake.Whether working with boards, executive teams, or engineers, my focus is consistent. Build clear systems, strong teams, and technology that creates real value.