Bridger has its roots in providing California auto insurance since 1974, and grew to become one of the state’s largest providers. When Bridger took over in 2017, it did so with the intent of continuing to build on a successful legacy.


Quite simply, we are bridging the past to the future through innovative insurance products and technology, designed for a new generation of users. Simplifying the transactional process of insurance and speed through which claims are filed is one of Bridger’s main goals.


With a broker network exceeding 1,500 locations, California auto insurance with Bridger is just around any corner. The company holds licenses in Arizona and Texas and is planning further expansion beginning in 2020.

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Our Team

Kimo Winterbottom

Chief Executive Officer

Gary “Kimo” Winterbottom is responsible for the strategic direction of the company, managing all of Bridger’s operating subsidiaries and all business development and capital raising activities. Kimo has acquired or launched 4 insurance companies and MGAs in the last 10 years, raising $80 million and producing an exited IRR of 37% between 2009 and 2017. Kimo holds a Bachelor of Arts in Economics from Santa Clara University and enjoys golf, skiing, contract bridge and rooting for his beloved San Francisco Giants.

Deane Silke


Deane brings over 30 years of insurance industry experience to Bridger with a specific focus in non-standard automobile insurance having spent 8 years at Bristol West (a carrier in the Farmers Insurance Group) in a marketing roleand prior to this Deane worked as a private passenger auto and commercial underwriter at Robert Moreno and Associates.Deane is a Chartered Property and Casualty Underwriter (CPCU) and in his 12years at Fiesta in a critical role helped steer the company through an unprecedented growth path in moving from one state and 7 offices to 5 states and over 200 offices using the Fiesta franchise model...

Matt Reznicek


Matt is jointly responsible for Bridger MGA’s product management, underwriting and claims operations. Prior to Bridger, Matt was Head of Product/Pricing at a regional auto insurance underwriting company through a period of topline growth from $100M to $300M. He also held Product Manager and Director, Emerging Markets roles at a publicly traded insurance company, leading efforts in Hispanic market expansion and direct to consumer sales. Matt earned a BA, Economics at Harvard College. Outside of work, Matt enjoys punting a football to his kids, chatting about Alabama football, and learning more about the universe..

Gerald Gruska


Gerry brings over 30 years of successful sales, marketing, and agency operations knowledge to the ever-changing Insurance industry. His understanding and expertise in building strong and profitable business relationships is well respected and acknowledged throughout many states in the insurance community. Gerry’s entrepreneurial spirit and understanding of the insurance market allows him to strategically support agents and companies with an enthusiastic and genuinely friendly attitude, that radiates a sincere passion for delivering value and benefits to his clients and coworkers. His drive to continually helping agents accomplish goals and benchmarks both personally and professionally best define his leadership abilities.

DeeDee Engel

Chief Administration Officer

DeeDee organizes and coordinates departmental operations, implements policies, develops process improvements and leads Human Resources that includes benefits administration, employee development, HR compliance and retention initiatives. DeeDee is also the Corporate Secretary and is responsible for all corporate matter that include managing all Board communication and logistics, maintaining the corporate records and ensuring that the corporation is complaint with all laws and regulations. Prior to Bridger, DeeDee was with SCJ insurance Services for 22 years as SCJ’s Director of HR and Corporate Administration.

Musa Elshiek

Senior Software Developer

Musa has over 30 years’ experience in the information Technology field, big part of it in the insurance industry. Musa has led efforts in designing, programming and implementing a highly efficient Policy Processing System, generating over 1.6 billion Dollars in revenue. With Bridger passion for technology and innovation, Musa has teamed up with its IT staff in bringing forth leading edge technologies to help support and enhance our insurance platform. With the goal of making interacting, and doing business with Bridger, an effortlessness experience.