Upside Appoints Chuck Hector as Chief Revenue Officer to Accelerate National Expansion in Housing-First Health Care
Hector brings more than 25 years of experience scaling revenue organizations across Medicare Advantage, Managed Medicaid, and commercial payer markets.
FORT LAUDERDALE, FL — Upside, the only housing stability platform purpose-built for healthcare, today announced the appointment of Chuck Hector as Chief Revenue Officer. Hector will lead Upside’s go-to-market strategy and enterprise expansion across a wide range of payer segments, including Medicare Advantage, Managed Medicaid, commercial plans, employer-sponsored coverage, group Medicare, ACOs, and health systems.
Hector brings more than 25 years of experience building commercially successful companies in value-based care. As a founding executive at Circadian Health, he helped launch the first virtual-first specialty care platform for chronic cardiometabolic conditions, integrating diagnosis, remote monitoring, and specialty treatment to close care gaps and reduce avoidable hospitalizations. Prior to Circadian, he served as Chief Revenue Officer at Papa, scaling the senior care startup to a $95M+ revenue run rate while supporting over 75 health plans nationwide. He also spent eight years at MDLIVE, overseeing sales, implementation, and client success — contributing to the platform’s growth to 35 million covered lives and positioning it for acquisition by Evernorth.
Across his career, Hector has participated in raising over $1 billion in capital, scaled organizations from $0 to over $2 billion in enterprise value, and built commercial teams that drive sustained, diversified growth across public and private payer markets.
“Chuck has a rare track record of building high-performing, multi-threaded revenue engines in healthcare,” said Jake Rothstein, Co-Founder and CEO of Upside. “He’s scaled sales and service teams across government and commercial lines of business while maintaining a relentless focus on outcomes. With housing now at the center of how health care organizations approach social determinants of health, Chuck’s leadership will help position Upside as the definitive infrastructure partner in this space.”
In his new role, Hector will be responsible for advancing Upside’s payer strategy, revenue operations, national accounts, and growth partnerships. His arrival marks a strategic inflection point for the company as demand accelerates for scalable, accountable housing solutions that directly support clinical performance and member retention.
“Housing is the most underleveraged social determinant of health, and Upside is reimagining it as a care delivery asset,” said Chuck Hector, Chief Revenue Officer of Upside. “This is a company poised to lead a systemic shift in how payers care for their most vulnerable populations. I’m excited to help scale a model that delivers both human impact and bottom-line results.”
Hector holds a BA in English from the University of Illinois and an MBA in Healthcare Administration from the Lake Forest Graduate School of Management. He will continue to reside in Fort Lauderdale, FL.
About Upside
Getting housed takes knowledge, time, and money. Most people are short at least two. Upside is a housing stability platform that brings all three — partnering with health plans and employers to find members and employees facing housing instability and work the problem to completion. Dedicated Care Guides, housing specialists trained in behavioral health engagement, own each case from first call to signed lease, supported by AI-assisted housing orchestration built to make them faster, not replace them. Upside serves Medicaid, Medicare Advantage, D-SNP, commercial, and employer-sponsored populations across the full housing continuum, from crisis to long-term tenancy support. Founded in 2020 and headquartered in Fort Lauderdale, Florida.