Winter Street Ventures is a healthcare-focused venture capital firm founded in 2016 by Chris Palmieri. Originally created as the venture capital affiliate of Commonwealth Care Alliance, the firm transitioned into an independent investment platform in April 2025 following the acquisition of CCA by CareSource. Headquartered in Boston, Winter Street Ventures builds on Palmieri’s deep healthcare industry experience to back companies that improve outcomes, lower costs, and enhance the patient experience.
The firm invests in tech-enabled healthcare companies, with particular emphasis on artificial intelligence and predictive analytics. Its portfolio themes include improving healthcare delivery, enhancing efficiency in systems, and driving patient-centered innovation.
Winter Street Ventures typically backs companies operating at the intersection of healthcare services, technology, and data, where measurable impact can be demonstrated.
In September 2025, Winter Street Ventures announced the launch of its inaugural independent vehicle, Winter Street Ventures Fund I LP. The firm is targeting $100 million in commitments for this fund.
Fund I is structured to invest in early-stage healthcare technology companies that use AI, data, and predictive analytics to modernize the delivery of care. The fund is designed to capitalize on the growing convergence of healthcare and technology, building on the prior track record achieved when the firm was affiliated with CCA.
Palmieri’s prior investments through Winter Street Ventures yielded a reported 520% total return, or 5.2x multiple on invested capital. These results provide the foundation for Fund I’s strategy and positioning, which aims to back healthcare innovations that are scalable and defensible while offering measurable improvements for patients and providers.
Leadership
The firm is led by founder and General Partner Chris Palmieri. Palmieri has over 30 years of leadership experience in healthcare, having served as chief executive officer at six healthcare organizations, several generating revenues exceeding $2 billion annually. In addition to his executive roles, he has held board positions at major trade organizations including the Association of Community Affiliated Plans (ACAP), where he was a long-standing chair, and America’s Health Insurance Plans (AHIP). His reputation as both an operator and investor positions him to bring strategic insight and deep networks to the companies Winter Street Ventures supports.
Investment Strategy
Winter Street Ventures seeks to identify and support companies at the early stages of development, focusing on innovations that leverage technology to solve systemic inefficiencies in healthcare. The firm looks for opportunities where AI and predictive analytics can improve patient outcomes, lower operating costs, and enhance accessibility. It aims to partner closely with founders, providing not only capital but also industry expertise, regulatory insight, and access to networks of providers and payers. The strategy builds on Palmieri’s track record of identifying differentiated healthcare models with both financial return potential and measurable patient benefit.
Notable Investments
Prior to its independence, Winter Street Ventures invested in 10 healthcare companies under Palmieri’s leadership. Examples include a tech-enabled provider of healthcare and social services for low-income populations that generated a 55.1x realized return, an API-connected fintech-as-a-service platform for healthcare infrastructure with an unrealized 4.7x return, and a SaaS data management platform for risk adjustment that delivered a 2.1x realized return. These investments highlight the firm’s focus on highly specialized, technology-forward healthcare solutions with strong market adoption.
Notable Exits
Exits to date include the realized investments mentioned above, such as the tech-enabled provider for low-income and diverse populations and the SaaS platform for risk adjustment. These outcomes underline the firm’s ability to identify scalable business models that achieve both financial success and meaningful healthcare impact.
Other
Founders should note that Winter Street Ventures is newly independent and currently building its first standalone portfolio under Fund I. This means its investment activity is ramping, and portfolio companies may benefit from heightened attention and resources as the firm establishes its brand in the venture ecosystem. Palmieri’s operating background and board leadership at national health insurance associations provide portfolio companies with unique strategic access to payer networks and policy insight. Given the fund’s thematic focus, startups applying cutting-edge AI and analytics to healthcare delivery are likely to align most closely with the firm’s mandate.
