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

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....

Answer Engine Optimization (AEO) for Early Stage Companies

In our latest session from the Mucker Growth Series featuring Ethan Smith from Graphite, we explored AEO, a significant new approach for optimizing visibility in AI-driven search, particularly relevant as...

Startup Guide to AI Visibility: Be the Brand ChatGPT Recommends

Introduction Today, users aren’t just searching on Google. They’re asking ChatGPT, Claude, Google’s Gemini, Perplexity, and other AI systems for advice. AI visibility is the new frontier of brand awareness....

Practical Uses of AI & Automation for Startup Operations

In a recent Mucker Growth Series session, we invited Rock Vitale, Founder & CEO of Easie, to share how he’s helped early-stage teams move from manual, fragmented workflows to streamlined,...

2025 New York Tech Week Recap Of Mucker Sessions

Last week during New York Tech Week 2025, we joined more than 1,000 events hosted by founders, investors, and VCs. This post is a full Mucker recap of the three...

How to Build a Customer Support Function for Startups Using AI Tools with Alex Velinov

Delivering high-quality customer support can be one of the most resource-draining parts of a startup. The good news: we’re at a turning point where founders can use AI tools to...