Why I built Ledger & Oak.
Jason Cannaday, Founder and Chief Financial Architect
THE ARMY
I enlisted in 2003 as a wheeled vehicle mechanic and deployed to Iraq with Operation Iraqi Freedom III. My team inspected and tested 300 factory-built armored Humvees before they went into use. That job taught me something I still work by. You check the thing that will fail before someone depends on it.
THE HOSPITAL
After Texas Tech I joined University Medical Center in Lubbock as a financial analyst. I spent seven years inside a large hospital's Decision Support stack. I led the implementation of a new operational budgeting platform, rebuilt a $450 million operating budget in it and trained more than 200 people to use it. I also built net revenue models from commercial payer contracts. That is where I learned what good Decision Support can do when a hospital has analysts and enterprise software.
THE CFO CHAIR
In 2016 I became CFO of StarCare Specialty Health System, a 500-employee mental health, substance use and IDD provider. I led a fiscal team of more than 60 people across accounting, payroll, billing, IT, purchasing and plant operations. We replaced a dated accounting system, implemented flex budgeting and built the infrastructure to produce state cost reports and waiver forecasts on a schedule instead of in a scramble.
LEDGER & OAK
Those two jobs showed me both halves of the same problem. Large systems have the tools and the people. Rural hospitals, behavioral health centers and nonprofits carry the same decisions without either. I founded Ledger & Oak in 2025 to close that gap - senior judgment, the data infrastructure underneath it and automation for the parts that should never take weeks again.
WHAT DRIVES ME
I am a husband and a father, and our family of five is the reason behind most of what I do. Building Ledger & Oak is part of how I provide for them, and part of how I hope to show my kids what it looks like to build something worth building.
I have also never been content to stand still. I am committed to growing every year, as a leader, as a professional and as a person, and I expect this firm to keep growing in the same way.
Most of all, I want to leave a mark. God blessed me with a particular set of skills, and I believe they are meant to be used for the people and communities that need them most. Ledger & Oak is how I put them to work.