Ken Dickinson

Throughout my career I’ve been drawn to periods of transformation: modernizing engineering organizations, rebuilding technology platforms, and helping executive teams navigate disruptive technology. The work I care most about isn’t implementing any particular tool. It’s building the operating models, engineering organizations, and executive alignment that let a new capability become a durable one. Most recently, that has meant building an enterprise AI function from the ground up for a century-old regulated insurer: defining strategy and governance, presenting directly to the board, and bringing production agentic systems into an environment where security, trust, and reliability are non-negotiable.

Before Jewelers Mutual, I led engineering, cloud infrastructure, and quality organizations at Pelago, SingleStore, and SAS, scaling global teams, modernizing platforms across AWS, GCP, and Azure, and carrying products from biannual releases to continuous delivery. Different industries, different technologies, but the same thread runs through all of it: technology becomes a competitive advantage when an organization changes how it works, not just what it buys. I believe AI will prove as foundational to business as the internet or the cloud, and that the lasting advantage will belong to organizations that learn faster, adapt faster, and redesign how people and technology work together.

The conversations I enjoy most are with leaders working through the same questions I work on every day: how to turn AI from a promising experiment into a real organizational capability. If that’s the conversation you’re having, I’d welcome hearing from you.