Skip to main content
Jason Kestler

Jason Kestler, CLTC®

Executive Vice President, Head of Cross-Channel Distribution


Jason A. Kestler, CLTC® serves as Executive Vice President, Head of Cross-Channel Distribution, for Highland Capital Brokerage. Since starting in the financial services industry in 1997, Jason has employed innovation and determination in his marketing efforts. His goal is to build the organization every day, ensuring a long and prosperous future for Highland and its representatives.

Jason’s unique management style and outside-the-box thinking have been featured in magazines such as Inc., Direct Marketing, Fortune Small Business, and Senior Market Sales.

Continuing with his busy lifestyle, Jason is a founding Annexus Group partner, based in Scottsdale, Arizona, and a founding Market Synergy Group partner, based in Topeka, Kansas. In addition, he is a two-term board member with the National Association of Fixed Annuities (NAFA). In addition, he is the former Secretary of the National Association of Fixed Annuities (NAFA) Board of Directors. He is also the founding Chairman of Insurance Marketers Advisory Council (IMAC) and has served on multiple insurance carrier advisor boards.

In 2018, Jason received alumni status from Harvard Business School (HBS) after graduating from HBS’s Advanced Management Program. 

Jason lives in Purcellville, Virginia, with his wife Emily, daughter Grace, and son Tripton.

Registration Form

  • Must be at least 8 characters in length, and include three of four of the following:
    • An uppercase character
    • A lowercase character
    • A number
    • A symbol
Are you currently working with Highland?
Are you a licensed Agent?