John Bennett

Managing Director, Citrin Cooperman Digital | AI & Microsoft Growth Leader | Healthcare AI (Azure OpenAI, Epic/FHIR) | Dynamics 365, Power Platform, Copilot | Ex-Microsoft, RSM, Sutter Health

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About

John Bennett is an enterprise AI and Microsoft growth leader with deep roots in healthcare. He helps health systems and mid-market enterprises put generative AI and automation to work on the Microsoft cloud, with ROI first, phased delivery and no pilot purgatory.

At Citrin Cooperman Digital he leads engagements across Microsoft Dynamics 365, Power Platform and Azure: ERP/CRM modernization, Power BI reporting, governed data platforms, Copilot and agentic automation for professional services, manufacturing and distribution, healthcare and financial services. Because the practice sits inside a top-tier accounting and advisory firm, its technology work is tied to finance and operations results.

His career spans both sides of the table. At Microsoft he worked with healthcare organizations on Microsoft Cloud for Healthcare. At RSM he led AI and automation for major U.S. health systems alongside CIO, CMIO and CTO stakeholders. At Sutter Health he led strategy and business development. Earlier he was a P&L owner, worked at Oracle, and founded and built a software company through two exits.

Selected results

$6M / $279MDirect and related revenue at Microsoft, from 20+ customer commits with Providence, Intermountain, Cleveland Clinic, CVS, Sutter Health, Wellstar, Scripps, Inova and Yale New Haven.
60–85%Less manual processing from GPT-powered revenue cycle automation for health systems (RSM, Azure OpenAI, Epic/FHIR).
3:1–5:1 ROIFrom AI patient-messaging triage workflows for healthcare providers (RSM).
$6M + $250MA new recurring revenue stream and a $250M pipeline with $45.5M in active proposals at Sutter Health.
$6.2M raisedFounder of TransDecisions. Sold one business unit to Bentley Systems and positioned another for acquisition by Servigistics, which PTC later bought for $220M.
P&L, 25+ teamVP at Hunt Energy IQ, leading restructuring with a $10M+ budget.

Experience

  1. Managing Director, Citrin Cooperman Digital. Dynamics 365, Power Platform, Azure data and AI.
  2. Director, Artificial Intelligence & Automation, RSM. Healthcare AI strategy for major U.S. health systems.
  3. Director, Industry Solutions – Healthcare Industry Specialist, Microsoft
  4. Chief of Strategy & Business Development, Sutter Health
  5. Vice President, Hunt Energy IQ (Hunt Consolidated)
  6. Business Development – Principal Solution Engineer, Identity Management, Oracle
  7. Founder & VP Business Development, TransDecisions
  8. Solution Architect, Oracle

Education: The University of Texas at Austin (BA, Geography and Business). Studies at the University of Oxford and Universidad de Salamanca.

Expertise