Rob Chesney
COO, Trunk Club
Rob Chesney currently serves on the Board of Directors for multiple companies: MAX, Cameo, and LandscapeHub. Rob was previously the Chief Operating Officer for Trunk Club. He was previously an EIR in Greylock Partners’ Silicon Valley office. Prior to joining Greylock, Rob was a Vice President at eBay, having worked at the leading ecommerce company for eight years. 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. 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.
Content & Articles by Rob Chesney
Stop Hiding Behind Your Screen: In-Person Events Are How You Win in 2026
2026 is shaping up to be the year businesses rediscover the power of shaking hands, clinking glasses, and actually meeting their prospects in person. Don’t take my word for it...
Build Alignment Before You Burn Out
Everything Feels Urgent At early-stage companies, everything feels urgent: shipping product, closing customers, raising money. In that environment, planning can feel like a luxury, or even a liability. In my...
How To Use Reddit To Scale Organic Growth For Your Startup
In this Mucker Growth Series session, Colin Belyea, founder of Karmic and an expert in Reddit organic growth, breaks down how Reddit has become one of the most influential discovery...
Sales Comp Kick Start: Keys to Getting It Right as You Begin to Build Your Sales Team
Webinar Recap featuring Donya Rose, Managing Principal from The Cygnal Group Sales compensation is one of the most critical aspects of building a successful sales organization. Many early-stage founders stumble...
Austin Tech Week 2025 Recap
Mucker Capital hosted two powerful days of programming during Austin Tech Week, bringing together founders, operators, and growth leaders to share real-world insights from the startup trenches. Across four sessions,...
LA Tech Week 2025 Day 3 Recap: AI Search – Wednesday Oct 15
After two packed days exploring AI startup building and go-to-market growth, Day 3 of LA Tech Week shifted focus to the evolving world of AI Search, how new AI technologies...