Video: Meet the founder of Chicago’s Fastest Growing Cloud Software Company

by Pat Ryan
August 14, 2013

(This was originally posted on Pat's blog:

Fieldglass founder, Jai Shekhawat, shared his journey and lessons at July’s Chicago Founders’ Stories @ 1871. We had another sold out crowd join us @ 1871 for pizza, beer, and to hear Jai share his story and the incredible wisdom he has gained in building Fieldglass.

This is the eleventh installment of Founders’ Stories. If you would like to check out any of the prior videos from past events, you can see them here: Braintree Founder Bryan Johnson, Open Table Founder Chuck Templeton, Grub Hub Founders Matt Maloney and Mike Evans, Belly Founder Logan LaHive, Context Media Founders Rishi and Shradha, Siri Founder Dag Kittlaus, Starter League Founders Neal Sales-Griffin and Mike McGee, Centro Founder Shawn Riegsecker, or SAVO Founder John Aiello, or Trunk Club Founder Brian Spaly 

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.

My INCISENT Labs teammates and I have really enjoyed partnering and sponsoring all of the Chicago Founders’ Stories @ 1871. Since the event sold out, we recorded it and are putting it online for those who couldn’t make it. In the video, Jai shares the importance is first about the problem, not the product, how to pitch the problem, the difficulties of discovering a market fit in the B2B industry, and the challenges and lessons learned of scaling a business.


We hope you enjoyed this interview with Jai, and look forward to the next Chicago Founders’ Stories @1871.

Pat Ryan is a business and social entrepreneur who has created several high growth software companies as well as several innovative urban education initiatives as a social entrepreneur. Pat’s first company, FirstLook, was recognized by Inc Magazine in 2008 as the #4 fastest growing software company in the U.S. in its Inc 500 rankings – the highest ranking ever for a Chicago based software company. Pat is also the Founder of MAX as well as the Founder and CEO of INCISENT Labs, a platform and incubator for innovative, industry-changing technologies that spin out into high growth companies. MAX was created in INCISENT Labs where Pat and a team are currently incubating their latest start-up. Pat blogs at and can be reached on Twitter @INCISENTLabs

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