Josh Gray

Venture Partner

Phone: 312-520-1053


Assistant: Jessica Burgos

Josh Gray joined Insight in 2015 as a Venture Partner. He works closely with CEOs and their executive teams to drive growth, scale operations, and achieve better and faster results.  Josh currently serves on the boards of Unitrends, Ensighten and CloudCraze, and he works closely with others like Workforce Software and Achieve3000.

In 2013, Josh joined Oracle via its acquisition of BigMachines, where he served as General Manager of the BigMachines Express business. Josh started and grew BigMachines Express to a multi-million dollar business. He previously led BigMachines’ Customer Success team and served as Director of Business Strategy, managing growth and operational initiatives across the organization.

Previously, Josh held roles in both the public & private sectors. He worked for the Chicago Public Schools, served as Assistant COO for Obama for America, and consulted for the Boston Consulting Group (BCG). Prior to BCG, Josh spent four years as a venture capital and private equity investor with Lehman Brothers Venture Capital Group and Svoboda Capital Partners.

Josh holds an MBA from Harvard Business School and an MPA from Harvard Kennedy School, where he was selected as a Zuckerman Fellow. He graduated Phi Beta Kappa from the University of Michigan with a BA in Political Science.