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

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...

Zero → 100: The Exact Steps We Took to Close Our First 100 Paying Customers

Going from zero customers to 100 in just four months sounds impossible—unless you’re a founder willing to roll up your sleeves and hustle relentlessly. I’m Gaurav Bhattacharya, co-founder of Jeeva.ai,...

Unblocking Startup Growth: Best Practices for Sales Discovery & Qualification with Richard Harris

Startups are in a constant race against time and resources, navigating complex sales environments with lean teams and limited margins for error. In a recent session from the Mucker Growth...

The LinkedIn Playbook: How Startup Founders Can Stand Out & Scale

This LinkedIn Playbook is based on insights from a recent one-time Mucker Growth Session webinar featuring LinkedIn growth experts Alec Paul (Founder of SalesBrand) and Kyle Williams (Founder of Brickstack)....

DeepSeek vs OpenAI: Comparison Breakdown and What It Means For Your Tech Startup With Dan Cleary

In this recent webinar of our Mucker Growth Series, we discussed the evolving AI landscape with Dan Cleary, founder of PromptHub. He provided an in-depth breakdown of DeepSeek vs. OpenAI,...