Meet the Herd

Meet the Herd

Kevin Chidwick, Chief Executive Officer

Kevin joined Elephant Auto Insurance as CEO in January 2012. He lives in Richmond and is married with 2 children.

Kevin is a UK citizen, and was based there until the beginning of 2012 when he moved to Virginia to join Elephant. He is a Group Board Director of Admiral Group Plc., a UK listed insurance company, the parent company of Elephant.

Immediately prior to joining Elephant, Kevin was the CEO of, a UK subsidiary of Admiral Group. is a leading online insurance intermediary with a significant share of UK auto insurance distribution.

Kevin joined Admiral Group in 2005, becoming Chief Financial Officer in September 2006. Prior to Admiral, Kevin has been in financial services for over 25 years. He has held a number of senior roles in other insurance organizations including Finance Director positions within Cigna Healthcare and National Australia Bank. He is a fellow of the Chartered Institute of Certified Accountants and has an MBA from the London Business School.

Tim MacAleese, Chief Financial Officer

Tim is a founding member of Elephant Auto Insurance. In late 2008, he helped build the business case for Elephant—a startup direct-to-consumer auto insurance company based in Richmond, VA. In January 2009, Elephant launched its insurance product in the US. Since that date, Tim has helped lead the growth of the Elephant “herd” from 3 employees to over 250 today, while also building the infrastructure and operations required to support (ultimately) millions of US auto insurance customers. On October 2, 2009, Elephant officially launched and began selling and providing auto insurance coverage in the Commonwealth of Virginia.

Prior to joining Elephant, Tim led the US consulting practice for the high-tech & telecom vertical at Gartner, Inc. Collectively, Tim has over 10 years consulting experience advising business clients across numerous industries, on sales and marketing strategy as well as general business operations. Tim began his career as a CPA, with four years of public accounting experience at Coles & Bodoin, LLP—a Boston-based regional firm. Tim holds a Bachelors of Science degree in Accounting, with honors, from Babson College in Wellesley, MA and a Masters of Business Administration degree from the Darden Business School at the University of Virginia. Tim and his wife are residents of Glen Allen, Virginia where they busily raise four children. Tim is an avid Red Sox fan and enjoys coaching youth lacrosse and field hockey in his free time.

Greg Minkler, Marketing and Sales Director

Greg is the Head of Marketing at Elephant Auto Insurance—the US division of Admiral Group Plc. Since joining Elephant in April 2010, Greg has helped to develop and execute the company’s marketing strategy.

Greg began his career as a Business Analyst at Capital One in 1997, working on various projects including cross-sell strategy, inbound and outbound marketing, and affiliate partnership development. He then moved to San Diego in 2003 to join Fair Isaac to manage product marketing for several financial service enterprise software products. Looking to return to Richmond in 2006, Greg took a position as the Director of Product Marketing with Affinion Loyalty Group, overseeing a team of product managers responsible for the product development and management in support of multiple loyalty clients. After 4 years at Affinion, Greg had the chance to join a dynamic new company in Richmond called Elephant. And after several meetings with the existing Elephant team, it was clear to him that this was a rare and exciting opportunity to be part of something great.

Greg brings a combination of direct response experience, analytical skill, and creativity to the marketing function at Elephant.

Greg received his undergraduate degree from Cornell University and his MBA from the Krannert School of Management at Purdue University. He is married and has two children.

Brian Wakefield, Vice President/ Head of Claims

Joining Elephant Auto Insurance in March 2009, Brian was charged with creating the Claims department. With him, Brian brings 15 years of prior automobile insurance claims leadership to Elephant. In addition to serving as the head of the Claims department, Brian leads Elephant Auto Insurance’s Risk Management Committee, as well as serving on the company’s Pricing Committee.

Brian earned his B.S. in Biology from Christopher Newport University in 1991. After working as an Environmental Tech, and Quality Control Chemist, he joined Progressive and entered the world of automobile insurance claims in 1994. During his 15 year tenure at Progressive, Brian led multiple business units and was selected for Progressive’s National Claims Strategic Steering Team. The Team twice re-engineered Progressive’s approach to processing claims. In 2000, Brian created the prototype design and workflow for Progressive’s Concierge Claims Service.

Kevin Whitehouse, Information Technology Director

Joining Elephant Auto Insurance in February 2012, Kevin was charged with leading the Information Technology department. Kevin brings over 20 years of experience in Information technology to Elephant. In addition to serving as the head of the IT department, Kevin leads Elephant’s Business Continuity Committee, as well as serving on the company’s Risk Management Committee.

Kevin earned his B.S. in Computer Science from the University of Evansville in 1989. After working in software development for 10 years with Heilig-Meyers, he joined RoomStore.  Kevin would spend 11 years with RoomStore where he led their Information Technology organization, as well as served on the leadership team that led RoomStore out of Chapter 11 Bankruptcy Protection. During his tenure at RoomStore he launched their e-commerce operation and managed the technology integration of a 70 store acquisition.

Kevin resides in Mechanicsville, Virginia with his wife and two children.

Colleen Benzin, Director of Product

Colleen is Head of Product at Elephant Auto Insurance – the US division of Admiral Group PLC. Colleen joined Elephant in 2013 and is currently responsible for Elephant’s product development and retention strategies.

Colleen has 24 years of financial services industry experience. She began her career with GE Capital as a member of the Financial Management Program. Colleen held a variety of financial roles in GE Capital’s Retailer Financial Services and Global Consumer Finance businesses, including spending five years living and working in Asia and Europe.

In 2000, Colleen moved to Richmond, VA with GE Capital Financial Assurance, which later became Genworth Financial. Her insurance industry experience spans multiple product lines and distribution channels including commercial leadership roles in Business Development, Distribution, Product, and Marketing.

Colleen graduated from Black Hills State University in Spearfish, SD. She recently served eight terms on the Alzheimer’s Association’s National Board of Directors. Colleen lives in Richmond with her husband and son.