Michael Monson Joins Upside's Executive Advisory Board

The former Altarum CEO and Centene Medicaid executive will advise Upside on dual eligibles, long-term services and supports (LTSS), and the health plans serving the country's most complex populations.

FORT LAUDERDALE, Fla., Oct. 21, 2026 /PRNewswire/ -- Upside, a nationally scalable housing stability platform purpose-built for healthcare, today announced that Michael Monson has joined its Executive Advisory Board. Monson has spent two decades building and running Medicaid, Medicare, and LTSS businesses at national scale, most recently as Chief Executive Officer and President of Altarum and before that as Senior Vice President of Medicaid and Complex Care at Centene Corporation. At Upside, he will advise on dual eligibles, LTSS, and how housing stability fits into the programs built for the highest-need members in the country.

For members eligible for both Medicare and Medicaid, and for members receiving LTSS, where someone lives is a critical variable that impacts their health outcomes. It decides whether a discharge plan holds, whether a personal attendant can be scheduled, and whether a member stays in the community instead of a facility. Plans screen for housing instability and document it. Far fewer have a way to resolve it. That gap between identification and a signed lease is the one Monson will help Upside close for the populations where it costs the most.

"Michael has seen this problem from every side: a national Medicaid product line, a nonprofit running state programs, a decade serving on a board focused on LTSS quality, and the founding chair of the national association for MLTSS plans," said Jake Rothstein, Co-Founder and CEO of Upside. "He knows what a plan can operationalize and what dies in committee. Our dual eligible and LTSS work is growing faster than any other part of the business. He is the right person to pressure-test it and help it scale further."

"I have spent more than twenty years in Medicaid and Medicare, and I have seen how critical the social determinants of health (SDOH) are to ensuring people can live their best lives," said Monson. "Housing is the most critical SDOH — when it is solved, everything else starts to become possible for a person's independence and health. There's a lot of talk about solving this problem, but Upside is the only company actually doing it. They get people into a home and help keep them there. I'm excited to help them continue to expand their reach and improve countless more lives."

Monson's career spans payers, providers, and the public sector. He began in management consulting at McKinsey & Company, then moved to health care, first working at the Visiting Nurse Service of New York as Senior Vice President for strategy, innovation, and operational improvement, and then as Chief Administrative Officer and Vice President of Residential Services at VillageCare of New York.

At Centene, Monson held national product management responsibility for Medicaid and complex care lines covering more than 12.5 million members across 30 states. He also served as Chief Executive Officer of Social Health Bridge Trust, Centene's social determinants of health initiative.

As CEO and President of Altarum, he led a successful turnaround of the organization and deepened its work with state government.

A national leader in LTSS, Monson founded the National MLTSS Health Plan Association and served as its Chair for four years. He also served on the board of the Long-Term Quality Alliance for a decade and as its Chair for two years. A member of the National Academy of Social Insurance, Monson holds a Master of Public Policy from the Harvard Kennedy School and a BA in communications from the University of Pennsylvania.

Monson joins a board and advisory group drawn from health plans, state Medicaid leadership, employer benefits, and venture capital. Upside serves Medicaid, Medicare Advantage, D-SNP, commercial, and employer-sponsored populations, supporting members in 15 states across the full housing continuum, from crisis placement through long-term tenancy support.

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.

SOURCE Upside