Rob Chesney

Venture Partner

Rob is an experienced Internet entrepreneur and operator with more than 17 years experience building and leading startup organizations.  He recently joined Chicago Ventures as a Partner 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.

Rob Chesney