Jason Cannaday

Chief Financial Architect and Founder of Ledger & Oak

Jason Cannaday is the Chief Financial Architect and founder of Ledger & Oak. A U.S. Army veteran with more than two decades of executive finance leadership in community healthcare, Jason is a recognized cost-report automation expert who pioneered statewide electronic cost-reporting initiatives for Texas healthcare providers. He specializes in helping Community Health Centers, rural hospitals and behavioral health organizations turn fragmented financial, clinical and grant data into real-time decision support through integrated data warehouses, custom BI tools and AI-driven reporting. His practical approach to service-line optimization, revenue integrity and financial resilience has enabled healthcare leadership teams to replace months of manual work with actionable, board-ready intelligence that maximizes reimbursements and strengthens organizations under evolving regulations like OBBBA.