Rob Sadow

Vp, Head Of Operations & Strategy

Rob Sadow is a seasoned executive and angel investor with a diverse background in operations, strategy, and entrepreneurship. Currently serving as the VP and Head of Operations & Strategy at Headway since February 2025, Rob contributes to building an accessible mental healthcare system. Previous leadership roles include CEO and Co-Founder of Flex Index, the top global insight platform on flexible work, and CEO and Co-Founder of Scoop Commute, which became the leading enterprise carpool solution. Rob's experience also includes a fractional COO role at Seso Inc. and extensive consulting at Bain & Company. An active angel investor since August 2020, Rob supports innovative startups across various sectors. Rob's educational background includes a BSE in Management, Legal Studies & Business Ethics from The Wharton School.

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