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Jon Dingledine has a diverse work experience spanning over several companies and roles. Starting in 1990, they worked as an Account Executive at Provident Life and Accident until 1993. Jon then served as the Director of Sales at Healthsource North Carolina from 1993 to 1996. Afterwards, they joined Prudential Healthcare as the Director of Sales and Account Management until 1999. Following this, they worked as a Consultant at BB&T Insurance Services Inc. from 1999 to 2002.

In 2002, Dingledine joined UnitedHealth Group, initially as a Senior Account Executive responsible for Key Account self-funded business in Central/North Florida markets. Jon'srole expanded to include Commercial and Public Sector new business clients for the entire state of Florida. From 2006 to 2012, they held the position of Director of Sales and Account Management at UnitedHealth Group, leading the new business and renewal efforts for the company in eastern North Carolina in the Key Account segment.

In 2012, they transitioned to Hill, Chesson, & Woody, where they served as the VP of Consulting. In this role, they led the Consulting team responsible for client retention and developed and implemented new solutions and strategies for clients across all products and funding.

In 2016, Dingledine joined Aetna, a CVS Health Company, as a Vice President. Jon held this position until 2019 when they joined Banner | Aetna in the same role of Vice President. The exact end date of their tenure at Banner | Aetna is not specified. Throughout their career, Dingledine has demonstrated strong leadership skills, client management expertise, and the ability to develop and communicate innovative ideas.

Jon Dingledine received a Certificate in Innovative Healthcare Leadership from Stanford University Graduate School of Business in 2019. Prior to that, they obtained a Bachelor's degree in Finance, General from The University of Tennessee at Chattanooga from 1987 to 1989.