Jon Stone
BRIEF DESCRIPTION
I build AI into enterprise platforms where every output has to survive an audit. I founded RationalAI to do that work as a fractional Chief AI Officer, for healthcare operators, the private equity firms that own them, and the investors looking at buying more.
Healthcare was the proving ground. It is the most heavily regulated market in software, and getting the model right turns out to be the easy part. The hard part is everything around it… the problem statement, where the data came from, the orchestration, validation and whether any of it still holds up a year later when somebody asks. I spent 15 years as a C-suite executive in healthcare technology, learning that the hard way. I co-founded Clearwater and served as Chief Product Officer while it grew to more than 650 healthcare customers, ranked number one by KLAS for Security and Governance Software in 2026 with 98.2% customer satisfaction and number one by Black Book for eight consecutive years.
I architected IRM|Pro, Clearwater’s patented risk management platform. More than 300 enterprise clients adopted it, including over 60 Fortune 500 health systems. I put machine learning risk scoring directly into the analyst workflow, which raised analyst productivity 40% and improved retention. It was not a pilot. It ran in production, inside a regulated workflow, with auditors on the other side of it.
I am a named inventor on three U.S. patents in machine learning applied to healthcare cybersecurity (US 12,079,348, US 11,620,390, and US 10,496,827).
I have also sat on the operator side of two private equity recapitalizations, building the technology narrative through diligence, value creation planning, and the work after close. Investors who hire me get an advisor who has been on the receiving end of the questions.
I teach what I practice, as faculty at The University of Texas at Austin in Leadership in Healthcare Cyber Risk Management and at IANS, where I advise CISOs across Fortune 500 healthcare, financial services, manufacturing, and government. I hold AIGP, CRISC, HCISPP, and PMP, plus executive programs in machine learning at MIT Sloan. I still build agentic systems myself, on the theory that you cannot govern what you do not understand.
My method is deliberately unglamorous. Pilot first. Prove the return before scaling anything. Design the security and the HIPAA compliance in at the start rather than bolting them on the week the diligence team arrives.
People ask why Formula One cars go so fast. It is the brakes. Good controls are what let you take the corner at speed.
My Credentials
I help healthcare companies get real results from AI without handing an attacker a new way in.