Vice President of Customer Success, Castlight Health

Gary Alpert has over 20 years of leadership, general management, marketing, sales, venture fundraising, M&A, and business development experience at mission-driven entrepreneurial organizations. Gary is currently an executive at Castlight Health, the leading provider of healthcare transparency solutions for employers and payers. Previously, he was Vice President of Business Development at, the leading consumer website focused on eldercare, where he was responsible for Caring’s extensive partnership and content licensing programs, working with organizations including MSN, Yahoo!, AOL, the Alzheimer’s Association and others to drive new revenue opportunities. Prior to Caring, Gary was the CEO and co-founder of WetFeet, Inc., a leading provider of recruitment software and management services to corporations, universities, and job seekers worldwide, from its founding in 1994 until its acquisition by a global employer branding consultancy in 2006. Gary earned an MBA and Certificate in Public Management from Stanford University’s Graduate School of Business and a BA in Human Biology from Stanford University.