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Rob Chesney is a seasoned businessman, entrepreneur, and investor, currently serving as a Partner at Chicago Ventures.
Rob Chesney joined Chicago Ventures as a partner, where he supports the overall management of the fund and is responsible for deal sourcing, diligence and associated activities. He also serves as General Partner and Entrepreneur Partner & Advisor.
Rob Chesney was the Chief Operating Officer at Trunk Club starting in December 2011. Most recently, he ran the company's Buyer Experience team. Trunk Club was sold to Nordstrom for more than $350 million.
Rob Chesney is a former Executive in Residence at Greylock Partners.
Rob Chesney is a Partner at Chicago Ventures, a venture capital firm. In this role, he contributes to the overall management of the fund, including deal sourcing and diligence processes. Before joining Chicago Ventures, Chesney held a significant leadership position at Trunk Club, a personal styling service acquired by Nordstrom. He notably ran the company’s Buyer Experience team, overseeing one of its largest business segments. Trunk Club was eventually sold to Nordstrom for over $350 million.
Chesney’s career also includes a tenure as the Chief Operating Officer at Trunk Club, a position he held starting in December 2011. Prior to this, he gained experience as an Executive in Residence at Greylock Partners, a venture capital firm known for investing in technology companies. His background also includes an entrepreneurial partner and advisory role at Chicago Ventures, indicating a long-standing involvement with the firm. His career trajectory demonstrates a consistent focus on technology startups, venture capital, and operational leadership.
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