Rob Chesney

Former Entrepreneur in Residence



Rob is a former EIR at Greylock Partners. In that role he advised entrepreneurs who were looking to scale their early stage startups and turn them into thriving, independent companies. His particular interest was in consumer-focused businesses with e-commerce, marketplace or payments-related business models. Rob has led small and large teams through periods of hyper growth, intense change and fierce industry competition. He is now COO of Trunk Club, joining the mission to re-invent the way men buy clothes

Prior to joining Greylock Rob was a Vice President at eBay. Most recently he ran the Company’s Buyer Experience team where he oversaw the Company’s largest business verticals including fashion, technology, media, collectibles and home. These verticals represent more than half of eBay’s $2 billion North America business. Prior to running eBay’s Buyer Experience team Rob was VP and GM of eBay Motors, which he joined shortly after it launched in 2001. When he left the group it was eBay’s largest stand-alone vertical. eBay Motors receives more than thirteen million unique visitors a month, ranking it in the top 10 for e-commerce properties.

During his eight-year tenure as a General Manager at eBay, Rob managed teams across sales, business development, product management, engineering and customer service, as well as brokered partnerships and led acquisitions. He launched eBay’s first local classified offering, executed the company’s first social media integration and initiated eBay’s first private sale.

Rob graduated from the Kellogg School of Management at Northwestern University and earned his bachelor’s in economics at McGill University. Rob was born and raised in Toronto.