Head down, grades up: Making it big in Chicago

Jai Shekhawat stood out from the other MBA students in Howard Tullman’s class at Kellogg School of Management 22 years ago. He sat in the back row, never raised his voice, and kept a low profile. Rather than talk about his aspirations or accomplishments, he came to class prepared, and it quickly became evident that he was putting in the work behind the scenes to make big things happen.

“Jai is just as kind and self-effacing today as he was then,” Howard confides.

So how has Jai changed? Far from sitting in the back row today, he has successfully founded and sold a business for $1 billion, and is considered one of Chicago’s most successful entrepreneurs. In 2012, Jai was named Ernst & Young’s 2012 Midwest “Entrepreneur of the Year”, and has been recognized as an innovator in the Vendor Management Software (VMS) space.

In 1999, Jai took what he had learned from Howard and others and channeled it into a project that addressed a problem he was deeply familiar with. He started Fieldglass, a company that offers the world’s most widely used Cloud platform for the procurement of contract labor and services.

Over the past two decades, Jai and Howard have kept in touch and maintained a student/mentor relationship that has blossomed into a friendship. Howard credits Chicago’s unique business culture in part for helping to make Jai a success.

I know of few people with more enthusiasm, and being in his class gave me the confidence to eventually find my own path as an entrepreneur.

— Jai Shekhawat

“Chicago is different,” says Howard. “People here are loyal in a way that perhaps you don’t see on the coasts — we’re in it for the long haul. Loyalty is a competitive midwestern advantage, and we also have an economy that is good for entrepreneurs who have diverse interests.”

Chicago can’t take all the credit, though. Howard taught Jai early on that it takes five things to be successful as an entrepreneur: passion, preparation, perspiration, perseverance, and principles. These “5 Ps” are instilled in many of the young, hopeful entrepreneurs that come to Howard’s prestigious startup incubation program, 1871 Chicago. And Jai gives credit where it’s due.

“Back then and right up to today, I thought of Howard as half teacher and half preacher. He’s always spreading the gospel and excitement of innovation and entrepreneurship. I know of few people with more enthusiasm, and being in his class gave me the confidence to eventually find my own path as an entrepreneur.”

Always the teacher, Howard deflects with more praise of Jai’s work ethic.

“Of course everybody wants to be the next Jobs, but with Jai, we sensed that he had the determination to be really successful. Perhaps more important than talent or anything else is the ability to keep your head down and stay focused. Half the battle is keeping your butt in the chair. Jai’s got that.”

What does one do after selling a company for $1 billion? In Jai’s case, he’s staying active in the city’s entrepreneurial scene with Howard at 1871, but he’s also focused on making Chicago the best city it can be by way of social activism and community service. He is heavily involved with an inner city academic program called MetroSquash, which helps to teach underprivileged urban youth how to play the unlikely game of squash while devoting an equal amount of time to academics. In doing so, MetroSquash mentors teach them dedication and discipline,two traits that Jai discovered are crucial to making it in his much-loved city.


Howard Tullman is the former CEO of 1871 and the General Managing Partner for the Chicago High Tech Investment Partners, LLC and for G2T3V, LLC – both Chicago-based early-stage venture capital funds which has invested in more than 25 Chicago-based startups in the last two years. He is also the Chairman of the Endowment Committee of Anshe Emet Synagogue, a member of the National Advisory Council on Innovation and Entrepreneurship (NACIE); a member of Mayor Emanuel’s ChicagoNEXT and Cultural Affairs Councils; a member of the boards of the Innovate Illinois and Illinois Arts Councils; a member of President Preckwinkle’s New Media Council, an Advisory Board member of HighTower Associates, Built in Chicago, and Imerman Angels, and an Adjunct Professor at Northwestern’s Kellogg School, as well as a regular guest lecturer at the Northwestern University School of Law. Mr. Tullman is a graduate with Honors of Northwestern University (B.A., 1967) and of its School of Law (J.D., 1970), where he also graduated with Honors.

Jai Shekhawat is the founder of Fieldglass, now part of SAP. Fieldglass provides the world’s most widely used cloud platform for the procurement of contract labor and services. Under his leadership, the Fieldglass platform grew globally with users in 100+ countries. He is a former strategy consultant with McKinsey & Company where he served clients in areas of corporate strategy, technology and cross-border alliances, as well as a former senior executive at Syntel, a software services firm in Michigan. He is also a co-founder of Quinnox, an application outsourcing firm in Naperville, Illinois. 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, the Board of TiE Midwest and the Board of Metrosquash. He currently serves on the Board of Trustees of the Field Museum of Chicago 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. Read Jai’s full bio here.


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