Enterprise AI & Technology Executive · Raleigh-Durham, NC

Ken Dickinson

I help organizations turn AI into durable business capability.

Vice President of Engineering, Jewelers Mutual · Constellation Research AI 150

Ken Dickinson, wearing a charcoal blazer and open-collar white shirt, photographed against a warm gray backdrop.

The system

Executive intent becomes durable capability through a system, not a project.

  1. Executive intent
  2. Operating model
  3. Governance
  4. Data and tools
  5. Agents
  6. Evaluation
  7. Production
  8. Business outcome
The path I build against, from board-level intent through to a measured business outcome.

Point of view

  • AI is not another technology wave. It is a shift in how organizations operate, decide, and create value.

  • The companies that succeed will not be the ones experimenting with the most models. They will be the ones that change how they work.

  • Resilience is not a checkbox, it is a mindset. Great engineering is not about avoiding risk, it is about knowing which risks you can afford to take.

Proof

7 to 356

users

Enterprise AI adoption Jewelers Mutual

I built the enterprise AI function for a century-old regulated insurer from the ground up: strategy, a decentralized operating model, and responsible-AI governance that let business teams move without waiting on a central queue. It scaled enterprise AI access from 7 to 356 users across 11 business units.

~200

hours a month

Agentic automation in production Jewelers Mutual

Designed a production agentic workflow that eliminated approximately 200 hours of manual work each month. It runs in a regulated environment on AWS, where explainability, evaluation, and ethical controls are engineering requirements rather than afterthoughts.

334%

Engineering delivery velocity Pelago

Improved engineering delivery velocity by 334% through platform modernization, AI-assisted development, and operating-model transformation.

47%

Cloud operating costs SingleStore

Reduced cloud operating costs by 47% through architectural modernization and operational optimization.

Focus

  • Enterprise AI strategy

    Operating models that let business teams move without losing governance.

  • Engineering transformation

    Delivery organizations where velocity is sustainable rather than episodic.

  • Agentic systems

    Production agents in regulated environments, with evaluation built in.

  • Executive and board alignment

    Emerging technology translated into investment, risk, and governance decisions.

Recognition and credentials

Recognition
Constellation Research AI 150 2026 to 2027
Speaking
Constellation AI Forum 2026
Speaking
AllDayDevOps Engineering transformation and AI-enabled delivery
Board
Board-level AI advisor Strategy, governance, risk, and adoption reporting
Patent
System and Method for Dynamically Generated Reports US20170142548A1
Education
Duke University, Fuqua School of Business Chief AI Officer executive program, in progress 2026
Education
University of New Haven Computer Science

About

I have spent my career in periods of transformation. Modernizing engineering organizations, rebuilding technology platforms, and helping executive teams navigate disruptive technology. Before Jewelers Mutual I led engineering, cloud infrastructure, and quality organizations at Pelago, SingleStore, and SAS, scaling global teams 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.

Contact

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 is the conversation you are having, I would welcome hearing from you.