Ken Dickinson Technology & AI Executive
I build and modernize engineering organizations, operationalize AI, and put the systems, teams, and operating models in place that turn emerging technology into business results.
At Jewelers Mutual, that meant giving eleven business units the ability to build with AI while governance stayed central.
Access to increasingly capable models will not create durable advantage on its own. Companies need the architecture, operating discipline, governance, and leadership systems required to absorb new technology and turn it into measurable value.
7 to 570
Across eleven business units
~200
By a production agentic workflow
334%
Through platform, AI-assisted development, and operating-model change
47%
Through architectural modernization and operational optimization
Technology changes constantly. The leadership challenge remains the same: aligning ambition, organization, architecture, and execution to create measurable outcomes.
Clarify the ambition and outcomes that matter.
Build the foundations that are secure, scalable, and built to evolve.
Deliver value continuously with speed, quality, and customer focus.
Create measurable impact that compounds over time.
Standards, guardrails, and responsible use.
Measure, learn, and improve continuously.
Executive leadership is not about choosing between obvious answers. It is about knowing which tradeoffs create lasting advantage.
01
Decision
AI adoption
Jewelers Mutual
2024 — 2026
Executive takeaway
Empower teams closest to the problem while keeping the controls that protect the enterprise.
02
Decision
AI systems
Jewelers Mutual
2024 — 2026
Executive takeaway
In regulated environments, confidence comes from building measurement into the system itself.
03
Decision
Architecture
Jewelers Mutual
2024 — 2026
Executive takeaway
Sustainable speed comes from foundations that let every future product move faster.
04
Decision
Engineering system
Pelago
2023 — 2024
Executive takeaway
Speed is not a goal. It is a capability designed into the way we build.
05
Decision
Architecture + economics
SingleStore
2021 — 2022
Executive takeaway
The most effective way to reduce cost is to change the architecture that drives it.
Technology transformation is ultimately an organizational challenge. My role is to create the environment where teams can make better decisions, move faster, and build things that matter.
My role isn’t simply implementing AI. It’s building the operating models, engineering organizations, leadership alignment, and cultural change that allow AI to become a durable business capability.
Throughout my career I’ve been drawn to periods of transformation, whether modernizing engineering organizations, rebuilding technology platforms, or helping executive teams navigate disruptive technology.
I believe AI will become as foundational to business as the internet or cloud computing. The organizations that create lasting advantage won’t necessarily have the largest budgets or the most advanced models. They’ll be the ones that learn faster, adapt faster, and redesign how people and technology work together.
Multi AZ? Good, you’ve acknowledged the value of a resilient system, but you’re still vulnerable. Active/Active Multi Region? Fantastic! But are any of your primary value streams dependent upon third party sub processors? If so, you’re only as resilient as they are.
Resilience isn’t a checkbox, it’s a mindset. Great engineering isn’t about avoiding risk, it’s about knowing which risks you can afford to take.
Jewelers Mutual
Vice President, Engineering
Pelago (formerly Quit Genius)
Vice President, Engineering
SingleStore
Vice President, Cloud Infrastructure
SAS Institute
Vice President, Enterprise Quality
SAS Institute
Director, Research & Development
Lulu Press
Director of Software Engineering
Genesys
Group Manager, Senior Software Engineer
Subway
QA Analyst
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.