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Northwestern University - Kellogg School of Management, MBA 1996
Strategy, Finance, Decision Sciences
Birla Institute of Technology and Science, MMS 1984

Current Companies

CEO and Co-Founder
Co-Founder & Board Member

Former Companies

Engagement Manager

Former Financial Organizations

Head of Business Operations

Web Presences


Jai Shekhawat

Jai is the CEO and Co-founder of Fieldglass, which makes the world’s most widely used Cloud platform for the procurement of contract labor and services. Under his leadership, the Fieldglass platform has grown globally with users in 70+ countries, multiple languages and currencies and over $20 billion in annual spend. He is Ernst & Young’s 2012 Midwest “Entrepreneur of the Year” as well as the current recipient of the Peter Yessne Staffing Innovator Award, recognized for pioneering the Vendor Management Software (VMS) space. In 2010, Madison Dearborn Partners made a significant investment in Fieldglass, valuing the firm in excess of $220m.

Jai previously co-founded Quinnox, an application outsourcing firm in Naperville, Ill., with development and sales operations in multiple countries. Formerly, he was a strategy consultant with McKinsey & Co. in Chicago where he served clients in various industries in the areas of corporate strategy, technology and cross-border alliances. He also worked as a senior executive at Syntel, a software services firm in Michigan.

Jai has held various civic and board positions including serving on the Mayor’s Council of Technology Advisors (MCTA) for the City of Chicago, the Membership Committee of the Economic Club of Chicago and the board of TiE Midwest. He currently serves on the Board of Trustees of the Field Museum of Chicago, is a Board Member of Metrosquash and is a founding member of the Firestarter Fund, which mentors and invests in Chicago start-ups.

Jai holds an MBA with specializations in finance and strategy from the J.L. Kellogg School of Management at Northwestern University in Evanston, IL, and a bachelor’s degree in management science from the Birla Institute of Technology and Science in Pilani, India.

Recent Milestones


Company Date Round Size Participants
Retrofit 3/2012Venture Round$2.7M23



  1. Fitness startup Retrofit raises $2.7M from Chicago investors ( [edit]
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