Rob Chesney is a partner at Chicago Ventures. He previously held leadership roles at Trunk Club and eBay.
What Rob can write
Career
- Greylock Partners · executive in residence
- Trunk Club · COO
- Chicago Ventures · PartnerNow
Focus
Education
Also at Chicago Ventures
Alert me when Chicago Ventures is active
One email when Rob's firm raises a fund, adds a partner or shows new activity.
Send Mode VC your deck
Raising a pre-seed or seed round? We write $1M to $5M first checks and help founders with distribution. A partner reads every deck.
Send your deckQuestions
Who is Rob Chesney?
Rob Chesney is a partner at Chicago Ventures. He previously held leadership roles at Trunk Club and eBay.
How much does Rob Chesney invest?
Chicago Ventures has not reported a check size. It invests at seed.
How do I pitch Rob Chesney?
Email [email protected], the firm's inbox for founders, and name Rob in the subject. A warm intro from a founder Chicago Ventures backed works better.
What did Rob Chesney do before Chicago Ventures?
executive in residence at Greylock Partners; COO at Trunk Club.
Last updated 2026-10-15. Is this you? Ask for a correction.