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Core Member Turned Investor: FinTech Entrepreneur Chris Gardner is Underscore VC’s Newest Partner

The global pandemic has introduced all sorts of new headwinds and tailwinds. But one thing that hasn’t waned is the passion, drive, and innovation within the Boston startup community. Even TechCrunch noticed, calling this past season Boston’s scorching VC summer. At Underscore VC, we had our busiest period yet. We’ve made 16 new investments, 11 follow-on financings, added 15 new Core Partners to our portfolio companies, held 60+ Core events, and engaged 800+ Core Members.

To keep up with this powerful demand, we’re proactively building a new virtual venturing model, and it’s only natural that our investment team evolve with it. Today, we’re delighted to announce that FinTech entrepreneur and Boston native Chris Gardner has joined Underscore as our newest investing Partner.

The Underscore team first got to know Chris as a Core Member, and later as a Core Partner to Hi Marley. Over the past year, as an incredibly active Core Partner, Chris became a natural extension of our team, working with us to source, select, and build early-stage B2B SaaS companies in Boston. As Chris’s connection with the team and portfolio increased, we mutually realized it would be crazy to not make him an official Underscore Partner.

Boston Skyline

Aside from being a Bostonian through and through, which we naturally gravitated towards, Chris is a proven FinTech entrepreneur, having co-founded Paydiant, which was acquired by PayPal in 2015. (In fact, Underscore Founding Partner Michael Skok first met Chris when North Bridge, Michael’s previous firm, backed Paydiant.) Chris most recently led PayPal’s P2P, PayPal Here, and In-Store payments products, and previously led product diligence and integration on PayPal’s $2.2B acquisition of iZettle.

Prior to Paydiant / PayPal, Chris was CMO and Head of Products at ExtendMedia, a video content delivery and commerce platform that was acquired by Cisco in 2010. Additionally, Chris served as SVP of Products and Marketing at m-Qube, North America’s leading premium SMS mobile payments provider that was acquired by Verisign in 2006. He was also VP of Products and Marketing at edocs, Inc., an e-billing, payments, and customer self-service company that was acquired by Siebel Systems. Chris had an early start in mobile when he joined the founders of OmniBrowse, Inc. as VP of Marketing, and helped launch one of the first mobile data service providers in the US. OmniBrowse was acquired by Microsoft in 1999.

Chris’s last five roles all resulted in exits that created good outcomes for both employees and investors. You can dig into his career, passion for entrepreneurship, and lovable dry-humor in his blog post about why he went into venture with Underscore.

While Chris’ wealth of experience and know-how in business building will be invaluable, it is his proven good judgement and genuine appreciation for founders that make him a perfect addition to the Underscore team.

“I couldn’t be more excited to have Chris join the partnership,” said Underscore Partner, Lily Lyman. “Through his work as a Core Partner to Hi Marley, I saw the immediate value Chris brings to the table, especially around product and marketing. His deep experience and humble, unassuming nature enable him to quickly connect and build trust with founders.”

“Chris’ wisdom, compassion, and authentic founder-first attitude are highly coveted traits that founders look for in their investment partners,” said Mike Greene, Co-Founder & CEO of Hi Marley. “I also value his dedication to bringing together the best people to build the best companies. Chris is the perfect addition to the Underscore team.”

Mike isn’t alone in this regard. Other founders that we’ve recently backed alongside Chris (but haven’t yet announced) have described similar experiences when working with him.

Beyond his business expertise and superb people skills, Chris is a self-professed nerd and tech omnivore. And though he’s also dabbled in speech recognition, video streaming, mobile marketing, mobile messaging, e-billing, and document management, he’s best known as a FinTech entrepreneur.

While no investor at Underscore is focused solely on a single segment (we are people-first investors, after all), Chris will spend a good bit of time digging into the FinTech startup ecosystem. So if you’re passionate about exploring or building in the FinTech space, get in touch with him!

Now Hiring

And finally, since you’ve read all the way here, we’ve got one more piece of firm news for you. At Underscore, we believe entrepreneurship is a powerful source for good. That’s why we’re creating a virtuous cycle of investing, building, learning, and sharing lessons to enable future entrepreneurs. And while we’re beyond excited to have Chris on the team, we’re searching for an additional investing partner to join Underscore.

As First Round succinctly summarized, venture recruiting is typically run privately, with investors tapping into their existing networks for talent. This old system is problematic. It causes firms to miss out on incredible, diverse talent—while limiting equal opportunity for all. So, we’re following First Round’s example by opening up the search to anyone. Reach out to our search partner to learn more about the role here.

To learn more about Chris and the areas he’s already investing in, follow him on Twitter and connect with him on LinkedIn. And, as always, subscribe to the Underscore Core Bulletin for monthly investment updates and Core event opportunities!