Winter Street Ventures

Chris Palmieri, the firm's Founder and General Partner, leads all investment decisions. He previously served as CEO of Commonwealth Care Alliance, a Massachusetts managed-care organization focused on dual-eligible populations. His operating experience in care delivery and health plan administration directly shapes the firm's investment thesis and diligence process.

Winter Street Ventures originally operated as the venture investment arm of Commonwealth Care Alliance under Chris Palmieri's leadership. When CareSource acquired CCA in 2025, Winter Street Ventures was separated and became an independent entity with Palmieri retaining full control. The firm no longer has a structural or financial tie to CCA or CareSource.

The firm invests at the earliest stages — seed and startup rounds — across healthtech and healthcare services. Its strategy reflects a generalist venture approach applied entirely within healthcare, with an emphasis on companies that can navigate Medicaid, Medicare, and dual-eligible reimbursement environments. There is no disclosed interest in growth equity or buyout transactions.

Palmieri ran a health plan that managed full-risk capitation contracts for patients with complex medical and social needs. That experience gives him direct insight into the operational pain points and regulatory constraints that determine whether a healthtech startup can actually contract with payers. The firm's strategy is built around identifying founders whose solutions align with the economic realities of value-based care, rather than pursuing pure technology plays.

The firm deploys capital through Winter Street Ventures Fund I LP, a traditional venture fund vehicle. Fund size and limited partner composition have not been publicly disclosed. Given the firm's recent spinout, Fund I likely represents the first independent vehicle raised after separation from CCA.