Upside Taps Former Altarum CEO Michael Monson for Executive Advisory Board

Michael Monson, former Chief Executive Officer and President of Altarum and a former Centene Medicaid executive, has joined Upside's Executive Advisory Board, the company said on October 21, 2026. Upside announced the appointment in a PR Newswire release.

Monson's Role on the Upside Advisory Board

Monson will advise Upside on dual eligibles, long-term services and supports, and how housing stability fits into programs built for high-need members. He spent two decades building and running Medicaid, Medicare, and LTSS businesses at national scale, most recently as CEO and President of Altarum and before that as Senior Vice President of Medicaid and Complex Care at Centene Corporation.

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 CEO of Social Health Bridge Trust, Centene's social determinants of health initiative. He founded the National MLTSS Health Plan Association and served as its Chair for four years, and served on the board of the Long-Term Quality Alliance for a decade and as its Chair for two years.

Jake Rothstein, Co-Founder and CEO of Upside, said: "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." Rothstein added that Upside's dual eligible and LTSS work is growing faster than any other part of the business.

Monson said: "Housing is the most critical SDOH — when it is solved, everything else starts to become possible for a person's independence and health."

Upside's Funding and Employer Expansion

According to akta.pro company records, Upside has raised six funding rounds, including a $20 million Series A in June 2026 led by Aquiline Capital Partners and Flare Capital Partners. The company launched its Employer Solutions line of business in June 2026 with Brad Cillian as General Manager, opening a third core customer segment beyond Medicaid and Medicare Advantage.

Earlier Upside Board and Funding Moves

In September 2026, Liz Fowler, former CMS Innovation Center director, joined Upside's board of directors, PR Newswire reported. The company said at the time it was expanding its Medicaid, Medicare Advantage, and employer housing benefit business.

In July 2026, Seniorhousingnews reported that Upside closed a $20 million Series A funding round in late June, led by Aquiline and Flare Capital Partners, and had pivoted from deconstructed senior living to housing for healthcare. In June 2026, Refresh Miami reported the round was co-led by Aquiline and Flare Capital Partners, with participation from 645 Ventures, Freestyle Capital, Triple Impact Capital, and Techstars.

Monson's Advisory Board Start

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