Meet the Herd

Meet the Herd

Alberto Schiavon, Chief Executive Officer


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.

Brian Wakefield, Head of Texas Operations

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.