SG Chicago: From "Ultra Dull Business" to $1B Exit, The Fieldglass Story

Unlike many unicorns - companies with $1 billion exits - reported by the media, Fieldglass was not a few years in the making. The sale in 2014 to SAP for $1 billion occurred a decade and a half after Jai Shekhawat founded the company. Today, Fieldglass is one of the most recent and biggest success stories in the Chicago tech community. Startup Grind Chicago proudly hosted and learned from Jai this last month.

Watch the video interview of Jai Shekhawat of Fieldglass in Chicago now!

It took six years for Fieldglass to even become profitable, and the company also had to overcome two financial recessions as well as September 11th just to survive. The journey to get there is what Jai describes as “serendipitous”, a word he points out comes from a Persian fairy tale, "The Three Princes of Serendip," whose heroes were always making discoveries by accident.

Early Life & Education

Jai was raised in India in a military family. His dad was a submarine captain and moved Jai around the world. His journeys weren't all cities and sunshine: he remembers traveling to an eastern Russia town where temperature dipped to 20 degrees below zero. After college, Jai was on the move again to Georgia when a transfer with a tech company unexpectedly presented itself. After a few years, Jai pursued an MBA from Kellogg.

Starting the Perfect Dull Business

At this point he didn’t know what starting a company even meant and had not considered it. However, after business school and management consulting at McKinsey, Jai discovered that there was this “perfect ultra dull business” of vendor cost management as a service that was where he would stake his claim.

Over the course of fifteen years, Jai has amassed experiences on building a startup that could take up a whole book. 

Don't wait for the book: jump into his Startup Grind video! 

You'll hear how he endured rejection after rejection in Silicon Valley but years later received 18 investment offers for Fieldglass. Or you might enjoy how he, as the fifth entrant into a space, became successful by turning competitors into collaborators.