What does it take to build a billion-dollar company in an industry nobody was paying attention to?

In this episode of Inside the Spark, host Luke Tanen, CEO of Chicago Innovation, sits down with Jai Shekhawat, founder and former CEO of Fieldglass—the company behind the world’s largest platform for managing contract labor before its $1 billion acquisition by SAP.

Jai shares how he identified an overlooked market opportunity, scaled Fieldglass to serve customers in more than 100 countries, and built a company that transformed an entire industry.

The conversation also explores why he’s dedicated his post-exit career to investing in and mentoring Chicago’s next generation of founders, and what he looks for in today’s early-stage startups.

Whether you’re launching a startup, growing a business, or curious about what it really takes to build and sell a billion-dollar company, this episode is packed with lessons and insights you won’t want to miss.