Executive Management

Richard McCathron is our CEO and President and has served as a member of the Board of Directors since February 2017. Prior to Hippo, Mr. McCathron held senior executive positions at various insurance companies including First Connect Insurance as its President & Chief Executive Officer from October 2012 to February 2017, Superior Access Insurance as its President & Chief Executive Officer from June 2007 to October 2010 and Mercury Insurance Group as its Regional Vice President from April 2004 to June 2007. Mr. McCathron is both a Chartered Property & Casualty Underwriter and a Certified Insurance Counselor and sits on the board of directors of Spinnaker Insurance Company and First Connect Insurance. He is an advisor for several other InsurTech companies and holds a BS in Finance from Oregon State University.

Assaf Wand is a co-founder of Hippo, serves as Executive Chairman of our board of directors and was our Chief Executive Officer from October 2015 to June 2022. Prior to Hippo, Mr. Wand was the founder and Chief Executive Officer of Sabi Inc., a consumer goods company, from May 2009 to October 2015. Mr. Wand also served as a consultant with McKinsey & Company from August 2005 to December 2006. Mr. Wand holds an MBA from the University of Chicago Booth School of Business and a dual degree from the Interdisciplinary Center Herzliya in Israel for a B.A. in finance and an LL.B in law.

Stewart Ellis serves as Chief Financial Officer and oversees all financial functions of Hippo. Prior to joining Hippo, Mr. Ellis served as Chief Financial Officer at Activehours (d/b/a Earnin), a mobile fintech company, from April 2017 to February 2019. From July 2012 to April 2017, Mr. Ellis was employed by BloomReach, Inc., an enterprise software company where he served as Chief Financial Officer. Mr. Ellis also served as Vice President, Finance, and other roles, of 23andMe, Inc. where he was employed from September 2008 to July 2012. Mr. Ellis holds a Bachelor’s degree with a concentration in Economics from Harvard College and an MBA from Harvard Business School.

Simon Fleming-Wood has served as our Chief Marketing Officer since October 2020. Prior to Hippo, Mr. Fleming-Wood served as Chief Experience Officer of Tile, Inc. from February 2018 to April 2020 and as their Chief Marketing Officer from November 2016 to February 2018. Mr. Fleming-Wood served as the Chief Marketing Officer of Pandora Media, LLC from October 2011 to April 2016. Mr. Fleming-Wood holds a B.A. from Stanford University.

Lukasz Strozek serves as Chief Technology Officer at Hippo. He joined Hippo in December 2020 from ecommerce payments firm Bolt, where he was Vice President, Engineering. Prior to that, he co-founded Clara Lending, an online lender with a mission of making homeownership a reality, which was acquired by SoFi. At SoFi, he co-headed Engineering and was responsible for several of the company’s new products. Earlier, at Bridgewater, he partnered directly with founder Ray Dalio, translating his vision into technology products. He is a Harvard graduate and holds a Stanford MBA. Lukasz calls Oakland home, together with his wife, daughter and two pandemic cats.