Rob Chesney is a seasoned businessman, entrepreneur, and investor, currently serving as a Partner at Chicago Ventures. After joining Trunk Club as Chief Operating Officer in December 2011, Rob Chesney quickly established himself as a pivotal leader in the fast-growing personal styling service. In this critical role, he oversaw the company’s Buyer Experience team, which represented one of its largest and most vital business segments. Chesney’s operational leadership was instrumental in scaling the company, contributing significantly to its eventual acquisition by Nordstrom for over $350 million.

Currently, Rob Chesney serves as a Partner at Chicago Ventures, a leading venture capital firm. In this significant capacity, he plays a key role in the overall management of the fund, actively contributing to deal sourcing, comprehensive diligence processes, and strategic portfolio development. His work at Chicago Ventures continues to leverage his extensive background in operational leadership and entrepreneurial ventures, focusing on identifying and investing in the next generation of innovative technology startups. Chesney’s career trajectory showcases a consistent and successful dedication to the intersection of technology, entrepreneurship, and venture capital.

As a seasoned businessman, entrepreneur, and investor, his insights are highly sought after, reflecting his proven ability to guide companies from startup phase through major growth and acquisition. His strategic vision and hands-on operational experience make him a formidable asset in the venture capital landscape, continually driving value for portfolio companies and the fund alike.