Jai Shekhawat is a Partner at Chicago Ventures and an active angel investor who previously founded and served as CEO. See portfolio and contact routes.
Jai Shekhawat is a Partner at Chicago Ventures and an active angel investor who previously founded and served as CEO of Fieldglass, a cloud vendor management platform he scaled to a $1 billion sale to SAP in 2014[1][2][6]. Before entrepreneurship, he worked as a strategy consultant at McKinsey & Company and holds an MBA from Northwestern’s Kellogg School[2][6]. His investment thesis focuses on early-stage enterprise software, SaaS, and B2B healthcare technology startups, primarily within the Midwest and Chicago region[1][6]. He typically invests between $100,000 and $5 million, with a sweet spot around $1.5 million, and often serves as a board member or advisor rather than just a passive follower[3][2]. Notable portfolio companies include FourKites, Signal, Xaptum, Semantify, Fleet Complete, and the quantum computing startup Verve Romance[1][2][4]. Shekhawat is a founding member of the Firestarter Fund, which mentors and invests in Chicago startups, and he is recognized as one of Chicago’s busiest startup mentors with over 50 investments since leaving Fieldglass[1][2]. He emphasizes digging deeply into whether a problem is significant and whether the entrepreneur has a unique “righ
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