Underscore VC
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Here's the deal with Underscore: they've built something genuinely different with their 'Core Community' model where they profit-share with 100+ operators who actually help their portfolio companies. It's not just intro-making - these advisors have skin in the game because they get paid when companies succeed. The catch? You're basically getting a Boston-centric fund that's going through a major generational transition after co-founder John Pearce passed away and Michael Skok stepped back. New managing partner Lily Lyman has a reputation for extreme founder dedication (literally rerouting flights mid-vacation to meet founders), but the jury's still out on whether the community model scales as they grow. Their unicorns (Salsify, Project44) prove the model works, but expect heavy Boston bias and a very hands-on, relationship-intensive approach that some founders love and others find overwhelming.
- —Best for: Boston-area B2B SaaS founders who want hands-on support and extensive operator network
- —Watch out for: Heavy Boston bias and very relationship-intensive approach during leadership transition
- —Known for: Unique profit-sharing community model that actually puts advisors' money where their mouth is
Underscore invests in companies at the early stages of a multi-hundred billion dollar Trusted Cloud Intelligence transformation, partnering with exceptional entrepreneurs supported by the Underscore VC community and specific Core groups focused around everything from Blockchain, to AI/ML and Applications like Commerce. They back bold, brave entrepreneurs who have their own vision formed from understanding problems deeply, challenging the status quo and thinking big about the impact they are going to make when they execute persistently.
Pre-Seed check sizes between $500K-$1M, while Seed stage check sizes fall between $1M-$3M. Primarily a B2B software investor with about 50% of investments in B2B vertical SaaS and 50% in Fintech and Emerging Technology companies. Portfolio includes 2 unicorns (Salsify and Project44) and 12 acquisitions, with 60 active investments including key companies like Coda, Project44 and Salsify.
Founding Partner Emeritus at Underscore VC, previously built businesses from Enterprise Big Data & Analytics (AlphaBlox – acquired by IBM) to Security & Consumer products (Symantec UK), then joined North Bridge Venture Partners before co-founding Underscore VC in 2015 to help founders create enduring companies through the power of community. Now serves as a Founding Partner Emeritus, continuing to serve as a trusted resource to the Underscore team and portfolio.
FinTech entrepreneur and Boston native who co-founded Paydiant, which was acquired by PayPal in 2015 (Michael Skok's previous firm North Bridge had backed Paydiant). Praised by partners for his proven good judgement and genuine appreciation for founders, with deep experience in product and marketing and an authentic founder-first attitude.
Managing partner who has hard-pivoted international travel plans while pregnant and en route to a wedding to meet a founder, diverted a vacation to stop in London for one founder, and gone from Mexico to San Francisco to get in front of another. Known for a zen, self-effacing quality combined with determination - she once even offered to coach a kids' lacrosse team to get a deal done.
Recently promoted to Partner as part of Underscore's multi-generational team building approach. Named to EVCA's top 25 rising stars in venture capital list, recognized as one of the top emerging VCs.
General Partner and CFO who started as an operator over 25 years ago as an FPNA professional, worked at American Tower and became CFO of two venture-backed companies before joining Underscore in a dynamic role supporting both the fund back office and helping all portfolio companies build and grow.
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