Underscore VC

The partnership group — Michael Skok, John Pearce, Richard Dulude, and Lily Lyman — holds investment committee authority on all deals. Skok's profile as the founding partner and former North Bridge GP is the most externally recognized, but decisions are made collectively within the small partner team. The Core community influences sourcing and diligence but does not sit on the investment committee.

The Core community is a curated network of roughly 200 enterprise technology executives and operators who serve three functions: sourcing potential deals through their own professional networks, conducting technical and market diligence on prospective investments, and co-investing their personal capital alongside the fund. This is structurally distinct from a typical advisory board because Core members have meaningful financial exposure to portfolio companies through SPVs. The model borrows from larger multi-stage firms' scout programs but is unusual among dedicated seed funds in making the network a formalized part of the capital structure.

Underscore typically leads or co-leads seed rounds, writing first-check sizes that allow it to take meaningful ownership in portfolio companies. The firm reserves capital for pro-rata follow-on investments into Series A rounds, but its primary function is as an institutional seed lead, not a passive participant in syndicates. In its ecosystem, Underscore often syndicates with other Boston-area early-stage firms like .406 Ventures and Flybridge Capital Partners.

The firm is deeply embedded in Boston's enterprise software scene, with Michael Skok having co-founded the Future of Cloud Computing series and having held teaching roles at Harvard Business School on entrepreneurial finance. Through the Core community, Underscore maintains active ties to alumni networks from HubSpot, Akamai, and other Boston-area public enterprise companies. The firm often acts as a connective node between Boston-based technical founders and coastal venture capital, functioning as a local anchor rather than a remote participant.

Underscore concentrates exclusively on B2B enterprise technology and does not invest in consumer internet, hardware, biotech, or deep science startups. Within enterprise, the firm avoids vertical SaaS applications that lack a clear horizontal infrastructure component. The stated focus on 'cloud intelligence' — spanning SaaS applications, cloud infrastructure, and edge computing — functions as an explicit negative screen against anything outside enterprise software.

Underscore differs from generalist Boston seed funds by its tight B2B cloud and infrastructure focus, whereas peers like NextView Ventures invest across consumer and enterprise, and Founder Collective covers a wider stage range. Underscore's Core community model also creates a structural difference — most seed funds in Boston operate with traditional partner-driven sourcing, not a formalized 200-person co-investor network embedded in the capital stack.

Michael Skok was a three-time enterprise software entrepreneur before becoming a General Partner at North Bridge Venture Partners, where he invested in companies like Acquia, Demandware, and Mautic. His operator background means the firm emphasizes product-market fit frameworks and go-to-market structure in its diligence, rather than purely financial metrics. This founding story reinforces the Core community's operating-executive composition — the firm is built to assess technical and commercial viability through practitioner eyes, not just investor metrics.