Rob Chesney
Partner @ Chicago Ventures
Chicago, United States
Rob Chesney is a the Chief Operating Officer at Trunk Club since December 2011. Rob is a former Executive in Residence at Greylock Partners. In that role Rob advised entrepreneurs who were looking to scale their early stage startups and turn them into thriving, independent companies. Rob's particular interest was in consumer-focusedbusinesses with e-commerce, marketplace or payments-related business models. Rob has led small and large teams through periods of hyper growth, intense change and fierce industry competition. Prior to joining Greylock Rob was a Vice President at eBay. Most recently Rob 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 Vice President and General Manager of eBay Motors, which he joined shortly after it launched in 2001. When Rob left the group it was eBay’s largest stand-alone vertical. eBay Motors receives more than thirteen million unique visitors a month, ranking it in the top 10 for e-commerce properties. During his eight-year tenure as a General Manager at eBay, Rob managed teams across sales, business development, product management, engineering and customer service, as well as brokered partnerships and led acquisitions. Rob launched eBay’s first local classified offering, executed the company’s first social media integration and initiated eBay’s first private sale. Rob graduated from the Kellogg School of Management at Northwestern University and earned his Bachelor’s degree in Economics at McGill University. Rob was born and raised in Toronto.
- Total investments:
- 10
- Last investment:
- Lead investor:
- 50%
Last updated:
For AI agents: llms.txt
Industries Rob Chesney invests in
Stages Rob Chesney invests in
Countries Rob Chesney invests in
Investment Focus
Industry
- E-Commerce 3 (30%)
- Apps 1 (10%)
- Beauty 1 (10%)
- Gaming 1 (10%)
- Social 1 (10%)
Stage
- Seed 7 (70%)
- Pre-Seed 1 (10%)
- Series A 1 (10%)
- Convertible Note 1 (10%)
Investments
| Company | Description | Round | Links |
|---|---|---|---|
Guthrie AI
|
Guthrie AI uses AI to structure RFPs and project information, helping teams quickly understand jobs and bid more effectively. | $4M / Seed / Jul 13, 2026 | |
Ender
|
We believe portfolios are the future. We're a venture-backed startup based in Austin, TX on a mission to help every kid build one by creating a competition platform where kids can win cash prizes for building apps, games, websites, and other real-world projects. We're a team of game developers, educators, engineers, and designerspioneering the first learn-to-earn education model and are funded by some of the best investors in the education and gaming space. | $5.5M / Seed / Apr 01, 2022 | |
CoPilot
|
CoPilot is pioneering Assisted Commerce for big-ticket purchases – starting with cars. You are the one spending the money - shouldn't you have an expert on your side? We founded CoPilot to make that a reality. For the average car buyer, who is not a car expert or enthusiast, car shopping can be a time consuming, frustrating process that leavespeople feeling alone and disadvantaged. CoPilot is changing this dynamic. Like a trusted friend who is knowledgeable about cars, knows where to look and what to buy, CoPilot provides car shoppers with an expert partner who empowers them to discover the perfect car at the best possible price with ease and confidence. | $10M / Series A / Aug 19, 2020 | |
Hallow
|
Hallow is a Catholic prayer and meditation app that hopes to help folks grow closer to God. It helps in finding peace, deepen the relationship with God, and sleep soundly every night. It was founded in 2018 and is based in Chicago, Illinois. | $3M / Seed / Nov 01, 2019 | |
Tso Chinese Takeout & Delivery
|
Tso Chinese Delivery is a Chinese-American delivery and take-out digital restaurant - dishes are prepared and delivered from a central kitchen and customers use an e-commerce menu ordering platform. Kitchens are location agnostic, thus inherently scalable. The front-end and back-end software platform is designed to handle everything from thecustomer experience to the kitchen order management to the delivery tracking. It allows for multiple locations and is opened ended to adapt to future different cuisine concepts.There are currently 2 locations in Austin:Arboretum Crossing9333 Research Blvd Bldg E, Ste 402 Austin, TX 78759Cherrywood3909 N Interstate 35, Ste E-5 Austin, TX 78722 | $2.2M / Seed / May 26, 2019 | |
|
Tso Chinese Takeout & Delivery
|
Tso Chinese Delivery is a Chinese-American delivery and take-out digital restaurant - dishes are prepared and delivered from a central kitchen and customers use an e-commerce menu ordering platform. Kitchens are location agnostic, thus inherently scalable. The front-end and back-end software platform is designed to handle everything from thecustomer experience to the kitchen order management to the delivery tracking. It allows for multiple locations and is opened ended to adapt to future different cuisine concepts.There are currently 2 locations in Austin:Arboretum Crossing9333 Research Blvd Bldg E, Ste 402 Austin, TX 78759Cherrywood3909 N Interstate 35, Ste E-5 Austin, TX 78722 | $2.2M / Pre-Seed / May 26, 2019 | |
LandscapeHub
|
LandscapeHub is dedicated to streamlining the B2B procurement process in the Landscaping Industry. Buyers and suppliers increase efficiency, expand their networks and gain valuable market knowledge and insights by using LandscapeHub.LandscapeHub is a digital, B2B marketplace connecting buyers and suppliers within a central onlineplatform.LandscapeHub represents quality suppliers across the country, aggregating their available inventory and pricing, empowering buyers with a “one stop shop” buying experience. | $4.4M / Seed / Mar 14, 2018 | |
Beauty By Design
|
Beauty By Design is a modern technology-led retail called prescriptive commerce, which can prescribe the solution faster and more accurately using digital technology. Beauty By Design is a vertically integrated, personalized skincare platform that solves the well-known problem of selecting and buying the right skincare products for skin types. | $2.2M / Seed / Feb 06, 2018 | |
|
CoPilot
|
CoPilot is pioneering Assisted Commerce for big-ticket purchases – starting with cars. You are the one spending the money - shouldn't you have an expert on your side? We founded CoPilot to make that a reality. For the average car buyer, who is not a car expert or enthusiast, car shopping can be a time consuming, frustrating process that leavespeople feeling alone and disadvantaged. CoPilot is changing this dynamic. Like a trusted friend who is knowledgeable about cars, knows where to look and what to buy, CoPilot provides car shoppers with an expert partner who empowers them to discover the perfect car at the best possible price with ease and confidence. | $4M / Seed | |
|
CoPilot
|
CoPilot is pioneering Assisted Commerce for big-ticket purchases – starting with cars. You are the one spending the money - shouldn't you have an expert on your side? We founded CoPilot to make that a reality. For the average car buyer, who is not a car expert or enthusiast, car shopping can be a time consuming, frustrating process that leavespeople feeling alone and disadvantaged. CoPilot is changing this dynamic. Like a trusted friend who is knowledgeable about cars, knows where to look and what to buy, CoPilot provides car shoppers with an expert partner who empowers them to discover the perfect car at the best possible price with ease and confidence. | $3M / Convertible Note |
Co-Investors
About Chicago Ventures
Chicago Ventures partners closely with exceptional entrepreneurs building companies in undercapitalized high-potential ecosystems.
Chicago Ventures Contacts
| Name | Phone | Socials | |
|---|---|---|---|
Kevin Willer
Partner
|
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Lindsay Knight
Partner
|
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Peter Christman
Partner
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Rob Chesney
Partner
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Stuart Larkins
Co-Founder and Partner
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FAQ
What does Rob Chesney invest in?
Rob Chesney invests primarily in E-Commerce, Apps and Beauty startups, most often at Seed and Pre-Seed stage. Most of the 10 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.
When did Rob Chesney last invest?
The most recent investment recorded for Rob Chesney closed in Jul 2026. Shizune tracks 10 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.
Is Shizune's investor data accurate?
Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Aug 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.
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