Jason Cannaday

Commander
DISC Type : D

Founder & Chief Financial Architect at Ledger & Oak

Lubbock, Texas, United States

Overview

Jason Cannaday is a service-disabled U. S. Army veteran and seasoned financial strategist who founded Ledger & Oak. With over 18 years in healthcare finance, including a key role as CFO for StarCare Specialty Health System, he now provides fractional CFO services and AI-enhanced insights to startups and healthcare providers. He holds a Master of Science in Finance from Texas Tech University.

Outside of his entrepreneurial ventures, Jason is a recognized community leader in Lubbock. He has a demonstrated passion for important local causes, including advocating for mental health initiatives through partnerships with local organizations. His background as a veteran shapes his committed and accountable approach to his work and community involvement.

Unique fact: Jason was honored as one of the "20 Under 40" by the Young Professionals of Lubbock in 2018.

Personality Overview

Decisive

Candid & Clear

Risk-Taker

They like to act fast and expect others to do the same.  They respond well to strong and respectful communication. They are very proud of what they do.

Topics They Care About

Healthcare Finance
Has over 18 years of experience in the sector, including serving as Chief Financial Officer for StarCare Specialty Health System and as a Senior Financial Analyst at UMC Health System.
Startup Growth
His current venture, Ledger & Oak, focuses on being the "Architects of Your Financial Blueprint" for startups, guiding their strategic growth and operational excellence.
Fractional CFO Services
This is the primary service offered by his firm, providing bespoke financial stewardship and systems implementation for businesses without a full-time CFO.

Media Appearances

Jason has no verified media appearances

Work History

3-2025
Founder & Chief Financial Architect at Ledger & Oak
6-2011
VP of Finance and Co-Founder at Opportunity Asia Education Services
5-2016 - 2-2025
Chief Financial Officer at StarCare Specialty Health System
1-2013 - 4-2016
Senior Financial Analyst at UMC Health System
10-2009 - 1-2013
Financial Analyst at UMC Health System

Education

2002 - 2009
Master of Science in Finance from Texas Tech University - Rawls College of Business
2002 - 2009
Master of Science from Texas Tech University - Rawls College of Business

More Information

Social Presence :

Prographics :

Exp : 16 Location : Lubbock, Texas, United States Job Level : Leadership Designation : Founder & Chief Financial Architect at Ledger & Oak
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Insights For Selling To Jason

During A Call Or A Meeting

DO's

  • When negotiating terms, help them build an impression that they are the ones calling the shots
  • Be respectful but crisp
  • Speak about competitive differentiation that your product offers

DONT's

  • Don’t take too much time in sending them information if they ask for any
  • Avoid being too verbose
  • Don’t be in a rush to invite them for a social meet and greet

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Jason is

  • Confidence in impact is paramount to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Jason

  • If they are not convinced, they will have no hesitation in telling you the same.

Insights For Deal Planning

    How fast (or slow) will Jason move?

  • They can take decisions very fast if you manage to convince them.
  • Can Jason take some risk or not?

  • The risks don’t matter much to them.

You And Jason

Personality Compatibility


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