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Winter Street Ventures (WSV) is a Boston-based venture capital firm and healthcare innovation accelerator founded in 2016 by Chris Palmieri. Initially established as an internal venture arm of Commonwealth Care Alliance, WSV became independent in April 2025. The firm focuses on reengineering healthcare through innovation, technology, and artificial intelligence, aiming to transform healthcare delivery.
As of 2025, WSV manages a fund targeting $100 million, with a portfolio strategy that includes 10 to 15 companies per fund. The firm emphasizes operational support and governance rights, leveraging its extensive network in the healthcare sector. WSV's team comprises experienced professionals with deep industry knowledge, particularly in navigating the complexities of healthcare delivery.
WSV invests primarily in tech-enabled healthcare solutions, with a specific focus on Series A funding stages. The firm targets companies with revenues between $0 to $10 million that are approaching breakeven, ideally with a pre-money valuation under $30 million. Their investment strategy emphasizes board and governance rights, aiming for top-quartile returns.
WSV's investment thesis centers on tech-enabled healthcare, particularly in artificial intelligence and predictive analytics, to enhance care delivery and operational efficiency. The firm is particularly interested in patient-centered innovations that address the needs of underserved populations, including low-income and complex care patients.
WSV's portfolio includes several notable companies:
These companies exemplify WSV's commitment to investing in innovative solutions that improve healthcare delivery and patient outcomes.
Chris Palmieri: Founder and General Partner. Chris previously served as the CEO of Commonwealth Care Alliance, a complex-needs health insurer with over $2 billion in revenue. He established WSV as CCA's internal VC arm before leading its independence in 2025.
Jennifer Bell: Partner. Jennifer brings extensive experience in healthcare investments and operational strategy, contributing to WSV's focus on tech-enabled solutions.
Jack Santacroce: Partner. Jack has a strong background in venture capital and healthcare, focusing on identifying innovative startups that align with WSV's investment thesis.
Jason Helgerson: Advisor. Jason has significant experience in healthcare policy and management, providing strategic insights to WSV's portfolio companies.
Geoff Meyerson: Advisor. Geoff's expertise in healthcare technology and innovation supports WSV's mission to transform healthcare delivery.
To pitch Winter Street Ventures, founders should visit their website at winterstreetventures.com or email info@winterstreetventures.com. A comprehensive pitch deck is essential, including details about the business model, market opportunity, and team. WSV prefers pitches that highlight tech-enabled solutions in healthcare, particularly those targeting underserved populations.
Response times may vary, but founders should expect to hear back within a few weeks. Warm introductions can enhance the chances of a successful pitch.
In April 2025, Winter Street Ventures became an independent venture capital firm, having previously operated as an internal arm of Commonwealth Care Alliance. This transition marked a significant milestone for the firm, allowing it to broaden its investment focus.
In September 2025, WSV launched its inaugural fund, targeting $100 million to invest in tech-enabled healthcare solutions. The firm aims to support 10 to 15 companies per fund, emphasizing operational support and governance rights.
WSV has been featured in various media outlets, including the Boston Globe and Modern Healthcare, highlighting its commitment to transforming healthcare delivery through innovation.
What are Winter Street Ventures' investment criteria?
WSV primarily invests in tech-enabled healthcare solutions at the Series A stage. They look for companies with revenues between $0 to $10 million that are nearing breakeven, with a pre-money valuation ideally under $30 million.
How can I pitch to Winter Street Ventures?
Founders can pitch WSV through their website at winterstreetventures.com or via email at info@winterstreetventures.com. A detailed pitch deck should include information about the business model, market opportunity, and team.
What makes Winter Street Ventures different from other investors?
WSV emphasizes active governance and operational support, leveraging its extensive healthcare network to assist portfolio companies. Their focus on underserved populations sets them apart in the venture capital landscape.
What is the typical check size for investments?
WSV typically invests between $2 million and $8 million per deal, with reserves allocated for follow-on investments in successful portfolio companies.
What is the geographic focus of Winter Street Ventures?
WSV primarily invests in North America, concentrating on healthcare innovations that can significantly impact the region's healthcare delivery.
What kind of post-investment involvement can founders expect?
WSV provides active governance and strategic guidance, drawing on the team's deep industry experience to help portfolio companies navigate the complexities of healthcare delivery.
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