Our Leadership Team - Healthpocket

Millions of People Saving Billions of Dollars®

Leadership Team

The HealthPocket team came together with a passion to help healthcare consumers make sense of their options as they try to save on their out of pocket health costs. We have deep experience in technology, healthcare and insurance, and we have held executive positions in for profit and nonprofit sectors. We knew we could do better with HealthPocket.com.

Gavin Southwell

Gavin Southwell

CEO & President

Gavin Southwell was most recently Chief Operations Officer at Cooper Gay Swett & Crawford (CGSC), the largest independent global wholesale and reinsurance broking group with a network of 60+ offices across the Americas, Europe, and Asia, employing over 1,800 skilled professionals.

Gavin was responsible for the Group's operations and technology as well as establishing the commercial strategy for each region, the set-up of new offices and integration of acquired businesses, and the design and implementation of a Target Operating Model by business type.

Gavin has a detailed knowledge and experience of insurance having worked in senior executive positions for a broker, MGU, insurer and reinsurer with a proven track record of delivering enhanced performance with a customer focused approach.

Michael D. Hershberger

Michael D. Hershberger

Chief Financial Officer, Treasurer and Secretary

Michael D. Hershberger was appointed Chief Financial Officer, Treasurer and Secretary of the Company in September 2015. Prior to that, he has served in various roles at the Company including Senior Vice President of Finance and Business Development and Chief Financial Officer since 2011.

From 2005 to 2011, Mr. Hershberger served as senior manager at Baker Tilly, a full service accounting and advisory firm, where he was responsible for managing housing research. Previously, from 2002 until 2005, Mr. Hershberger served as president of Urban Solutions, Inc., a real-estate development firm. Mr. Hershberger also served as a lecturer at the University Of Wisconsin Graduate School Of Business in 2011 and 2012.

Mr. Hershberger served as chief financial officer of Health Plan Administrators, Inc. from 1992 to 2002, where he was responsible for oversight of financial reporting and financial operations.

From 1988 to 1992, Mr. Hershberger served as commercial loan officer at Draper & Kramer. He served as senior accountant at Coopers & Lybrand from 1985 to 1987. Mr. Hershberger holds a Bachelor of Science degree in accounting from Augustana College and earned his Masters of Science degree in urban land economics/finance from the University Of Wisconsin Graduate School Of Business. He is a Certified Public Accountant in the State of Illinois.

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