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Underscore VC functions as a Boston-based venture capital firm, dedicated to supporting early-stage B2B software entrepreneurs. The firm focuses its investments at the Pre-Seed and Seed rounds, aiming to provide more than just capital by actively partnering with founders. Its core approach involves a deeply collaborative model, designed to nurture portfolio companies through critical initial development phases.
Richard Dulude co-founded Underscore VC, establishing the firm based on a conviction regarding the specific requirements of nascent B2B software enterprises. The firm was built on the insight that early-stage businesses thrive with committed investor engagement, extending beyond financial transactions to include strategic support and operational guidance. This founding principle underscores their founder-first philosophy.
The primary beneficiaries of Underscore VC's model are ambitious B2B software innovators seeking foundational capital and experienced mentorship. The firm's long-term vision is to serve as a steadfast ally, empowering these entrepreneurs to transform innovative concepts into sustainable, market-leading companies. They aim to contribute significantly to the future landscape of business technology by fostering successful ventures.
Key people at Underscore VC.
# Underscore VC: Boston-Based B2B Software Investor
Underscore VC is a Boston-based venture capital firm founded in 2015 that focuses on early-stage B2B software entrepreneurs at the pre-Seed and Seed stages.[4][6] The firm operates with a distinctive mission to support bold entrepreneurs building iconic companies while creating a more sustainable and inclusive global financial system, as evidenced by its status as a Principles for Responsible Investment signatory.[1][2]
The firm's investment philosophy centers on a balanced portfolio approach, with approximately 50% of capital deployed into B2B vertical SaaS companies and 50% into Fintech and Emerging Technology ventures.[3] Underscore deliberately avoids biotech and FDA-regulated sectors, though it maintains strategic interest in healthcare and life sciences companies that operate at the intersection of SaaS and healthtech.[3] This focused thesis allows the firm to develop deep expertise while maintaining flexibility across high-growth software markets.
Underscore VC's most distinctive feature is its "open-source" investing approach centered around the Underscore Core—a curated community of top entrepreneurs, seasoned executives, rising stars, and domain experts.[2][3] Rather than simply maintaining a passive expert network like traditional venture firms, Underscore financially incentivizes Core Community members through profit-sharing arrangements, creating genuine alignment between advisors and portfolio success.[3] This model emerged from the firm's founding listening tour, where hundreds of entrepreneurs identified access to the right people at the right time as the critical success factor for scaling companies.
The firm goes beyond capital deployment by embedding experienced operators into its portfolio. Notable Core Limited Partners include Meghan Verena Joyce (former Uber and Oscar Health executive, now CEO of Duckbill), Steve Fredette (co-founder of Toast), Andy Palmer (co-founder of Tamr with 30+ years of scaling experience), and Amy Villeneuve (former COO and President of Amazon Robotics).[2] This depth of operational expertise translates into hands-on support for portfolio companies navigating product development, go-to-market strategy, and organizational scaling.
As a Boston-based firm, Underscore leverages proximity to one of the world's premier innovation ecosystems, providing portfolio companies with access to talent, capital, and institutional knowledge concentrated in the region.[2] This geographic focus enables deeper relationship-building and more frequent engagement with founders compared to distributed venture models.
Underscore's portfolio spans diverse B2B software verticals, including commerce experience management (Salsify), payment infrastructure (Pagos), vertical marketplaces (Mable), digital events platforms (Goldcast), AI-powered data protection (Orion Security), and healthcare technology (Quilt Health).[1] The firm has also backed companies like H1 and TetraScience at the healthtech-SaaS intersection, demonstrating its ability to identify emerging category leaders.[3]
The diversity of portfolio companies reflects Underscore's thesis-agnostic approach within its core B2B software focus—the firm prioritizes founder quality and market timing over rigid vertical specialization, allowing it to capture opportunities across multiple high-growth segments.
Underscore VC represents a meaningful evolution in venture capital structure, addressing a fundamental founder pain point: the gap between capital availability and actionable operational guidance. The firm's profit-sharing model with its Core Community challenges the traditional VC incentive structure where limited partners and GPs capture returns while expert networks remain undercompensated. This approach aligns with broader industry trends toward transparency, founder-friendly terms, and value-add beyond capital.
The firm's emphasis on diversity, equity, and inclusion—with firm-wide DEI goals reviewed bi-annually—positions it within the growing cohort of venture firms recognizing that diverse founding teams and inclusive investment practices drive both better outcomes and broader economic impact.[3] As institutional capital increasingly scrutinizes ESG alignment and responsible investing practices, Underscore's PRI signatory status and explicit commitment to sustainable finance provide competitive differentiation.
The Boston positioning also matters strategically. While Silicon Valley remains venture capital's traditional epicenter, the concentration of life sciences, healthcare technology, and enterprise software talent in Boston creates natural advantages for a firm focused on B2B SaaS and healthtech. Underscore effectively positions Boston as a credible alternative hub for ambitious founders seeking capital with operational depth.
Underscore VC has built a defensible model that addresses real founder needs through financial incentive alignment and operational depth. As the venture market matures and founders increasingly demand more than capital—seeking mentorship, network access, and strategic guidance—the firm's community-driven approach becomes increasingly valuable.
The firm's future trajectory will likely depend on several factors: (1) whether the Underscore Core model scales effectively as the portfolio grows, (2) how successfully portfolio companies leverage the advisor network to achieve outsized outcomes, and (3) whether the Boston hub thesis continues to produce category-defining companies competitive with coastal alternatives.
Looking ahead, expect Underscore to deepen its focus on B2B vertical SaaS and fintech while potentially expanding its healthtech thesis as regulatory environments evolve. The firm's commitment to responsible investing positions it well for an era where founder-investor alignment and sustainable business practices become table stakes rather than differentiators. For founders seeking capital paired with genuine operational partnership, Underscore represents a meaningful alternative to traditional venture models—one where the incentives genuinely align toward shared success.
Key people at Underscore VC.
