Rob Chesney

Rob is an experienced Internet entrepreneur and operator with more than 17 years experience building and leading startup organizations. He is a Partner and member of the Investment Committee at Chicago Ventures, where he supports the overall management of the fund and is responsible for deal sourcing, diligence and investment, and working directly with portfolio companies.

He has deep consumer and e-commerce experience and expertise having led multiple businesses through periods of hyper-growth. Most recently, Rob served as COO of Trunk Club where he played a central role in the general management of the company; overseeing customer acquisition, leading innovation of the technology platform and managing the build-out of the company’s operations. The company was sold to Nordstrom Inc. in 2015. In previous roles, Rob was an Executive in Residence at Greylock Partners and spent 8 years at eBay where he served in various roles, including Vice President of eBay Motors and Vice President Buyer Experience & Verticals for North America.

Rob grew up in Toronto and now lives in Winnetka with his wife Erica and their three children. Rob holds an MBA from Kellogg and a BA from McGill University.