Sheila has always been passionate about business and family. She graduated from Mount Holyoke College while juggling an Economics major and raising her oldest son. In her son's toddler years, she pursued dual degrees from Harvard Business School and Harvard Law School and was still able to work part-time as a consultant for Monitor Group. At Harvard, Sheila graduated with honors, and received two prestigious awards: the Dean's Award for overall leadership and contributions to Harvard Business School; and the Fitzie Foundation Award, given by the Margaret Fitzgerald Grogan Petersmeyer Foundation, which honors the most outstanding female students.

From there, Sheila went on to serve as an executive at several successful Internet companies—most notably: Upromise.com, an online service helping families save money for college; and TheLadders.com, an online service helping people find jobs. Care.com is a continuation of Sheila's pursuits to prioritize community involvement and helping people through successful Internet business strategy.

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