Benchmark taps ex-Stubhub president as new entrepreneur-in-residence

Early-stage venture capital firm Benchmark announced the appointment of Chris Tsakalakis as its newest Entrepreneur-In-Residence. Tsakalakis, who served as president of StubHub after leading eBay‘s acquisition of the company, plans to pursue new opportunities in e-commerce, marketplaces and health tech.

Press Release

Benchmark, the early-stage venture capital firm, today announced Chris Tsakalakis as its newest Entrepreneur-In-Residence. Tsakalakis is an entrepreneur and CEO with more than 25 years of experience developing and leading consumer and technology businesses, including leadership roles at StubHub and eBay.

“I’ve been following the Benchmark partners for more than 20 years, starting with Bill’s Above the Crowd newsletter in the early days of the internet,” Tsakalakis said. “I’m excited to be working closely with a team I highly respect to launch this next phase of my career.”

In this role, Tsakalakis plans to explore new business opportunities in the areas of e-commerce, marketplaces and health tech.

Previous entrepreneurs-in-residence at Benchmark include New Relic founder Lew Cirne, Nextdoor cofounders Nirav Tolia and Sarah Leary, current HackerOne and former Eucalyptus and MySQL CEO Marten Mickos, and Quip cofounder and former Facebook CTO Bret Taylor, among others.

“Great entrepreneurs are the lifeblood of what we do, and we’re looking forward to working shoulder-to-shoulder with an entrepreneur of Chris’ caliber on his next great venture,” said Benchmark General Partner Bill Gurley.

Prior to this role, Tsakalakis served for nearly eight years as President of StubHub, the world’s largest online ticket marketplace. He came to StubHub after leading eBay’s acquisition of the company in 2007. At eBay, he served as a Marketplaces executive for more than a decade, from 2003 to 2014.

Earlier in his career, Tsakalakis held management positions at two e-commerce startups, and was also a consultant with Bain & Company for six years. Today, Tsakalakis also serves as an advisor to startups including ZIRX, Diana Labs, and WineSimple.

About Benchmark

Benchmark invests in and works alongside entrepreneurs building startups into transformational companies. We focus on early-stage venture investing in mobile, marketplaces, social, and infrastructure and enterprise software. Benchmark is comprised of six equal general partners who take board seats and a hands-on approach to every entrepreneur and company. Benchmark’s current portfolio of early-stage venture investments includes private market leaders such as Uber, Snapchat, Tinder, Nextdoor, Stitch Fix, Docker and Cyanogen; recent IPOs and acquisitions such as Twitter, Instagram, Yelp, League of Legends, OpenTable, New Relic, Hortonworks, GrubHub, Zendesk and Zillow; and franchise companies from Juniper to eBay to Red Hat. Benchmark’s offices are in San Francisco and Woodside.


for Benchmark
Emmalee Kremer, 530-521-0466