Chris Palmieri has spent more than 30 years in healthcare, building and leading mission-driven organizations that serve patients across payers, providers, and government programs. He has served as Chief Executive Officer of six $1B+ healthcare companies, two of which he grew to $3B in revenue.

Most recently, Chris served as CEO of Commonwealth Care Alliance from 2015 to 2025, guiding the organization through a successful exit valued at over $800M to CareSource. He led Remedy Partners through its scaling from 4 to 40 states and its $405M acquisition by Signify Health (later acquired by CVS Health for $8B). He founded the health insurance division at VNS Health, driving $2.5B in topline revenue and returning $1B in surplus dividends over a decade. His earlier C-suite roles include leadership positions at Amerigroup Corporation, HomeFirst at MJHS, and Senior Network Health at Faxton St. Luke’s Healthcare.

Beyond his C-suite roles, Chris has served on the boards of leading health insurance trade organizations, including the Association of Community Affiliated Plans (ACAP), where he served as Chair for six years, and America’s Health Insurance Plans (AHIP) — organizations representing coverage for more than 200 million Americans.

At Winter Street Ventures, Chris has invested in 10 healthcare companies generating a 5.2x gross multiple on invested capital, including early-stage positions in Cityblock Health, Lynx, and instED. He brings the operator perspective to venture — sourcing through warm relationships built over three decades, underwriting with the conviction of someone who has run the businesses being evaluated, and engineering exits from the inside out.