Partner, Chicago Ventures
Rob Chesney 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 and verticals for North America. Rob holds a BA from McGill University and an MBA from Kellogg.