Rob Chesney

eCommerce-focused business builder

TaskRabbit, OneKingsLane, AirBnB

Getting ahead of yourself (strategically, hiring, expansion). It might feel like a sprint but it is definitely not a sprint, marathon is probably not the right frame of reference either.... think 10K.

Need to have the right attitude... be positive, be humble about what you know and be passionate

Prior to joining Trunk Club as COO, Rob was an EIR in Greylock Partners’ Silicon Valley office. In this role he advises entrepreneurs who are looking to scale their early stage startups and turn them into thriving, independent companies. He has a particular interest 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.
Prior to 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.