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Management

Gary Tolman, President & Chief Executive Officer
Gary has over 30 years of experience in the property and casualty insurance industry. Prior to joining Esurance, Gary was President of Talegen Holdings, Inc., formerly the property and casualty operations of the Xerox Corporation. Before Talegen, Gary worked at Fireman’s Fund Insurance Company for 15 years, ultimately serving as Senior Vice President.

Chris Henn, Managing Director – Chief Operating Officer
Chris has more than 20 years of insurance industry experience and leads Esurance’s product management, corporate services, internal audit, and customer service operations. Before joining the company, Chris was the Vice President of Auto Product Management with Nationwide Insurance. At Nationwide, he also served as Vice President and General Manager of Colonial Insurance. Prior to Nationwide, Chris was with Progressive Insurance Corporation for 10 years, finishing his last assignment as a Vice President in product management.

Jonathan Adkisson, Managing Director – Chief Financial Officer
Jonathan has over 15 years of insurance industry experience and is a Fellow of the Casualty Actuarial Society. He joined the company in 2000 and has served as our Chief Financial Officer since 2003. Prior to joining Esurance, Jonathan held various positions at Farmers Group in catastrophe management, corporate financial analysis, and actuarial. Jonathan started his career at X….

Esurance Ratings

  • 2.5
    coverage
  • 2.3
    cost
  • 1.9
    service
  • 1.7
    claims
  • 2.1
    overall rating

Based on 114 review – 1 is lowest, 5 is highest

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Phil Swift, Managing Director – Chief Information Officer
Phil has over 30 years of experience in engineering and information services. Before joining Esurance, he was Vice President of Engineering with eSubscriber. Prior to that, Phil was Vice President of Information Services with QRS, a business-to-business electronic commerce service for the retail industry. Phil has also held management roles at Visa International, Matson Navigation Company, and Fireman’s Fund Insurance Company.

John Swigart, Managing Director – Chief Marketing Officer
John has more than 10 years of insurance industry experience. He joined the company in 2000 and served as the Vice President of Finance for three years before becoming the Chief Marketing Officer in 2003. Before joining Esurance, John worked at Swiss Re, in both the Reinsurance and Capital Partners Divisions. Prior to that, he was a consultant at A.T. Kearney in the Financial Institutions Group. John began his insurance career at Mutual Benefit Insurance Company.

Wayne Sharrah, Managing Director – Claims
Wayne has more than 18 years of experience in the property and casualty insurance business, all in claims. He previously worked at Esurance’s sister company, OneBeacon, where he was Vice President of the commercial claims division. Wayne began his career at Progressive, where he spent 13 years in a variety of claims leadership positions.