Rob Chesney
General Partner at Chicago Ventures
Rob is an experienced operator and investor with more than 25 years of experience building, leading, and investing in startup organizations. He is currently a general partner 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 serves on the board of multiple early-stage companies including PreFix Inc., NOCD, and GreenLite Technologies.
As an operator, he has deep consumer and e-commerce expertise having led multiple businesses through periods of hyper-growth. Previously, 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 of Buyer Experience & Verticals for North America.
