Rob Chesney

Rob Chesney is a seasoned businessman, entrepreneur, and investor with a remarkable career spanning over 17 years in the dynamic landscape of investment and tech startups. As a founding partner at Chicago Ventures, a venture capital firm specializing in early-stage investments in tech startups, Chesney has played a pivotal role in shaping the success stories of numerous companies.

Notably, Chesney served as the Chief Operating Officer of Trunk Club, a trailblazing clothing subscription service. During his tenure, he orchestrated the expansion of the company’s online platform, demonstrating his strategic prowess in customer acquisition and operational efficiency. His impactful leadership contributed significantly to Trunk Club’s exponential growth.

Beyond his role at Trunk Club, Chesney has further solidified his influence in the business community by serving on the Board of Directors for several notable companies, including MAX Digital, LandscapeHub, Cameo, and CoPilot. Through these diverse roles, he has become recognized as a leader in the tech startup ecosystem, guiding companies towards prosperity.

Since 2018, as a founding partner at Chicago Ventures, Chesney has continued to make waves in the venture capital scene. Managing a portfolio of high-profile clients, he and his experienced team actively invest in and nurture the growth of promising tech startups in their early stages. Chesney’s dedication to fostering a thriving entrepreneurial community in the Chicago area reflects his commitment to shaping the future of technology.

With his wealth of experience and a track record of success, Rob Chesney stands as an inspiration to aspiring entrepreneurs worldwide, showcasing the transformative power of strategic leadership in the ever-evolving tech industry.