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.

Articles by Rob Chesney

LA Tech Week 2025 Day 2 Recap: Startup Growth – Tuesday Oct 14

After a packed AI Building Day, we continued LA Tech Week with Startup Growth Day, a full schedule of sessions focused on go-to-market strategy, founder journeys, and scaling startups in...

LA Tech Week 2025 Day 1 Recap: AI Building – Monday Oct 13

We hosted three full days of events during LA Tech Week, each one focused on helping founders learn, connect, and build with the latest in AI and startup growth. Day...

Using Customer Feedback to Build a Product that Customers Will Love

Customer feedback is the lifeblood of successful product development, but many startups struggle with collecting, validating, and prioritizing the constant stream of input from users, advisors, and internal teams. In...

Shaun Merritt Vibe-Coded Karrot.ai

How Shaun Merritt Vibe-Coded Karrot.ai As A Solo Builder

I recently had the opportunity to chat with Shaun Merritt, cofounder and CTO of Karrot.ai, a LinkedIn ABM tool. Shaun was kind enough to share a comprehensive breakdown of how...

7 Steps to Build a Product That Sells Itself

Learn the 7 steps to product-led growth (PLG) to build a product that sells itself. Drive activation, boost conversions, and scale efficiently with Wes Bush from ProductLed....
Balancing self-care and startup pressure as a founder

The Founder’s Mental Health Playbook: What I Learned After Nearly Burning Out

A hard-won guide to staying mentally healthy while building a startup I founded Stitcher, the podcast platform, in 2007 and ran it for seven years until we sold in 2014....

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