Winter Street Ventures (WSV) has a proven history of scaling transformative healthcare companies. Founded and relaunched as an independent fund by Chris Palmieri—a seasoned operator who has successfully guided multiple billion-dollar organizations through growth, turnarounds, and acquisitions—WSV is uniquely positioned at the intersection of healthcare delivery, technology, and public policy. Backed by a deep bench of partners and advisors with expertise spanning venture capital, federal health policy, and healthcare innovation, WSV is focused on identifying high-potential opportunities, engineering successful exits, and delivering top-quartile returns. With a differentiated focus on technology and AI-driven enablement, WSV combines operational know-how with strategic relationships across payors, providers, and health systems to capitalize on some of the most needed areas for healthcare innovation and disruption.
Investment Strategy
- Focus areas. Tech-enabled healthcare across three thematic buckets:
- ◦ Care Delivery — in-home care, value-based care enablement, care coordination, social care, specialty care
- ◦ Clinical AI — diagnostics, clinical decision support, predictive analytics for patient outcomes
- ◦ Operational AI — revenue cycle automation, prior authorization, workforce operations, process automation
- Stage. Series A focus (approximately 80%) with selective Seed investments (approximately 20%). Check sizes of $2M–$8M with capital reserved for follow-on rounds.
- Ownership. Target meaningful minority positions with board and governance rights. Pre-money valuation discipline at or below $30M — preserving multiple expansion at exit.
- Return objective. Top-quartile by Cambridge Associates and Preqin vintage benchmarks. Underwritten target: 4–5x at Series A and 7–10x at Seed.
Our Experience
- Track record. 10 healthcare investments generating a 5.2x gross multiple on invested capital, including a 4.7x unrealized return on an API-connected fintech-as-a-service platform for healthcare and a 2.1x realized return on a SaaS data management platform for risk adjustment.
- Proprietary sourcing. 10K+ companies in the WSV CRM, 100+ health system partners, 50+ payer organizations, and 150+ private equity, venture capital, and consulting relationships. 100% of investments come through WSV’s direct sourcing network.
- Value creation. Active portfolio engagement, board and governance support, commercialization guidance through WSV’s payer and provider relationships, and access to a deep talent and advisor network.
Our Approach
Winter Street Ventures is uniquely positioned to be at the frontlines of healthcare and the ongoing challenges and opportunities coming from both sides of the aisle. Our exclusive focus and value is harnessing this position to connect early stage companies and incumbents to transform healthcare.
Industry
Healthcare — tech-enabled services and AI-driven platforms
Size
$0–$10M,
approaching breakeven
Type
Tech-enabled services and
software businesses
Ownership
Meaningful minority position with board and governance rights
Customer
Care delivery, payers, and
government program partner
Stage
Series A focus (~80%);
selective Seed (~20%)
Check Size
$2M–$8M with reserves
for follow-on
Valuation
At or below $30M pre-money — disciplined entry pricing
Founder
Proven entrepreneurs with
experienced leadership teams
Our Team
Chris Palmieri
Chris has spent over 30 years within the healthcare industry from C-suite executive to healthcare-oriented Venture Capital investor. The top-quartile returns led by him at Winter Street Ventures lay homage to the healthcare industry and patients that it humbly serves.
Jennifer Bell
Jennifer Bell is a leading voice at the intersection of healthcare, federal policy, and strategic growth. As a founding partner of Chamber Hill Strategies — a certified women-owned, bipartisan public
Mentorship and Academic Engagement
Jason Helgerson
Jason Helgerson is the Founder and CEO of Helgerson Solutions Group (HSG), where he leads venture capital and private equity advising and drives international projects to transform health and social care. A nationally recognized healthcare reform leader, he previously served as New York State’s Medicaid Director, overseeing a $68 billion program and spearheading groundbreaking reforms that saved billions and advanced value-based care. He also held leadership roles in Wisconsin and remains active as a board member, advisor, and Aspen Institute Health Innovators Fellow.
Geoff Meyerson
Geoff Meyerson is the CEO and Co-Founder of Locust Walk, a global investment bank dedicated to advancing innovation in the life sciences. With deep expertise spanning investment banking, venture capital, and biotech business development, he has led more than 60 strategic transactions. He is also the Founder and President of BioBreak and an active leader in the life sciences community through board service, thought leadership, and industry networks.
Our Network
Our Approach
- Frontline thesis driven approach stemming from strategic relationships that are solving the pain points of healthcare today.
- Investing in companies that are looking to take on the status quo and challenge the existing assets in place.
- Clear opportunity to reduce systemic fragmentation and unnecessary gaps in care.
- Significantly de-risk traction and growth through our strategic customer relationships.
- Support portfolio companies to grow customer and revenue base.
- Differentiated service and technology models that can scale efficiently.
- Reputation as healthcare executive, founder, and investor that drive access to the best opportunities within our mandate.
- 100% of all investments come through our own direct deal sourcing network.
- Relationships with 150+ Private Equity, Venture Capital, and Consulting Firms across the US.
- Partnership with over 100+ health systems and 50+ payor organizations.
- Large network of entrepreneurs and founders
- Support management teams and co-investors with ability to serve on and lead boards.
- Leverage key stakeholders within healthcare that can provide expertise and commercialization opportunities.
- Network of C-Suite executives and former founders that provide advisory support.
- Access to a deep talent network across various industries in healthcare, finance, and operations.
- Network of financial sponsors and strategics that can provide robust exit opportunities.
- Access to a variety of back-office capabilities that can support the day-to-day management of any business.
- Relationship with multiple investment institutions looking to gain access to early-stage deals.
- Multiple approaches to exits and partial return realizations (venture engineering).
- Proven follow-on strategy that results in doubling down on winners and structured pro-rata rights.
- Non-cyclical