John Kelly
Fractional CTO & Technology Advisor at Crinaro.AI
Based in United States · 30+ years experience
Summary
CTO / CIO | I build AI products and the teams that ship them | Agentic AI & platform engineering | Technology Advisor
About
For thirty years I’ve built next best action platforms: systems that personalize the right next action for the right person at scale. The core concepts haven’t changed. How we deliver them has, as the technology has improved. I’m a technology executive who builds the platform and the team around it.
At TravelNavigator.com, which built the Yahoo Travel portal, that meant routing a shopper to a local travel agent when they wanted to buy in person. As head of technology at WinningHabits, it was one platform personalizing activity and wellness for health clubs, YMCAs and employers. At Cigna, my team’s next best action platform supported 4,000+ nurses in behavioral and disease management coaching, and let Cigna insource from a SaaS vendor and save $60M annually. At XiFin, it brought next best action to pharmacists at national retail and grocery chains including Walmart, Walgreens and CVS.Each of those platforms taught me the same thing: it only works when the organization around it is built the same way. I look at the organization as a system. That system has to be aligned to the value the organization is trying to deliver, and each team has to own its part of it. Once that alignment is in place, AI adds velocity, and it is no longer confined to engineering; it can accelerate the entire organization. At Accela I led the migration toward spec-driven development and collaborative AI agent teams, with a few teams already working that way.
I’ve done this across four consecutive CTO and CIO seats in health insurance, healthcare and SaaS, including building Cigna’s Clinical and Individual technology organizations from early-stage initial teams to steady state. I hold a patent (US 11,514,072 B1) for row-level data lineage, and I’ve supported SOC 2, HITRUST, HIPAA, PCI DSS and GovRAMP as the technology executive, plus SOX in a public company.
Next, I want to help organizations move faster while they manage their cost structure. If that is the problem you are working on, I’d welcome a conversation. Alongside that I run Crinaro.
AI, a side project where my own agent teams test these ideas against real work.
Dual Citizenship - Irish & US
Skills
Software Architecture, Cloud & Infrastructure, M&A / Due Diligence, Platform Modernisation, Engineering Leadership, Vendor Management, DevOps, Governance & Risk, Data & AI
Regions covered
Industry experience
Government, SaaS, Healthcare
At a glance
John brings hands-on experience across Software Architecture, Cloud & Infrastructure, M&A / Due Diligence, Platform Modernisation, Engineering Leadership, Vendor Management and 3 other areas. Available for engagements across United Kingdom, United States, Ireland. Industry experience includes Government, SaaS, Healthcare.
How fractional CTO engagements with John work
John works on a fractional basis — typically one to three days a week for an agreed engagement length — so you get senior technical leadership without the cost or commitment of a full-time hire. Engagements commonly include technical due diligence, board reporting, engineering team leadership, technology strategy, architecture reviews, hiring support, and stepping in as interim CTO during a transition.