Jai Shekhawat founded Fieldglass, which makes cloud-based software to manage the hiring of a flexible workforce, in 1999. The dot-com bubble burst, but Fieldglass survived: The company was sold for $1 billion in 2014.
“The main thing that helped us is that our conception of the original problem has never changed,” he told Blue Sky. “We’ve always framed it as helping firms manage a large contingent workforce. Our approach to solving it has evolved as the space has become more complex — say around compliance issues, cost control or workforce quality.”
Shekhawat previously founded application outsourcing firm Quinnox in Naperville. He has worked as a strategy consultant with McKinsey and as a senior executive at Syntel, a software services firm.
He earned his MBA with specializations in finance and strategy from the Kellogg School of Management at Northwestern University. He holds a master’s degree in management from the Birla Institute of Technology and Science in Pilani, India.
Ernst & Young named Shekhawat the 2012 Midwest “Entrepreneur of the Year” and he currently serves on the Board of Trustees of the Field Museum of Natural History. He is a founding member of the FireStarter Fund.
Shekhawat was named to the board of the Chicagoland Entrepreneurial Center, which runs 1871, in early 2015.