Proofpoint Capital

Co-Founders Dan Goldsmith, Jonathan Brassington, and Matt Wallach oversee investment decisions. The firm’s Principal, Jon Gulardo, leads deal origination, diligence, and execution. The partnership model relies on all three co-founders engaging directly with portfolio companies as active board members and operational advisors, drawing on their respective histories as CEOs and Presidents at scaled vertical SaaS companies.

The firm sources through the founders' 25-year networks in vertical software, especially former Veeva, Instructure, and Capgemini executives. Its 'Activated Operator Network' is described as a community of former operators who refer founders, provide diligence, and actively work alongside portfolio companies. The partners' personal track records — and endorsements from CEOs of portfolio companies like Veho and Artera — act as a founder-facing sourcing funnel.

Proofpoint Capital is structured as a venture firm, not a single family office. All three co-founders are active operators and investors, not stewards of a single-family pool of capital. The firm hires dedicated investment and operational staff, including a Principal and a Head of Finance & Operations, signaling a traditional fund management structure.

From its stated model, Proofpoint Capital focuses on direct early-stage investments. The partners invest their own capital and raise external funds, concentrating on high-conviction bets rather than primary fund commitments or secondaries. The team's prior experience at FFO Capital and Osage Venture Partners included fund-of-funds and secondary transactions, but Proofpoint’s public positioning centers on direct company building.

Proofpoint targets early-stage companies, described by the firm as partnering at the seed stage through early growth. The co-founders frame their support around scaling from startup to enterprise, covering initial product-market fit, senior team hiring, and board construction, rather than late-stage pre-IPO checks. Their most publicized endorsements come from founders they backed at the earliest stages of their ventures.

The firm concentrates on Vertical AI with declared core focuses on healthcare, life sciences, and financial services. Proofpoint’s website frames these as industries where domain expertise, proprietary data, and deep workflow ownership create competitive moats. While the partners’ experience covers broader vertical software, their current investment thesis narrows to these regulated, data-rich sectors.

Proofpoint Capital is a venture firm run by Dan Goldsmith, Jonathan Brassington, and Matt Wallach. It shares a name but has no corporate relationship to Proofpoint, Inc., the publicly traded cybersecurity company. The firm’s domain name and branding are distinct, and all of the partners' prior operating experience is in vertical software, not security infrastructure.