Upside, a scalable housing stability platform, has raised $20 million in a Series A funding round to continue addressing the U.S. housing crisis from a healthcare perspective.
Aquiline led the round, with participation from Flare Capital Partners and support from existing investors 645 Ventures, Freestyle Capital, Triple Impact Capital, and Techstars.
Housing instability is “one of the most persistent drivers of avoidable health care costs,” Dante La Ruffa, partner and head of venture and growth strategy at Aquiline, said in a statement.
“Upside has the model, team, and infrastructure to address that, and we’re excited to partner with them in their next chapter,” said La Ruffa. “We believe there is a significant opportunity to accelerate upside momentum through Aquiline’s strategic connectivity across health plan, payer and broker channels, and product adjacencies that further expand the company’s value proposition to all key stakeholders.”
The company plans to use the funds simultaneously in the Medicaid, Medicare Advantage and employer-sponsored markets. The company also plans to hire leaders and expand its operational capabilities.
Launched in 2020, Upside was founded by Jake Rothstein and Peter Badgley. CEO Rothstein previously co-founded Papa, which connects seniors and their families with Papa Pals. The company says it is the only nationally scalable housing stability platform purpose-built for healthcare. The organization works across 10 states, partnering with health plans and employers to identify and stabilize individuals experiencing housing instability before their situation becomes a medical crisis.
Upward executives say the company’s care model leads to employee benefits that cover housing guidance, rental and mortgage support, senior citizen transition planning, and savings assistance.
According to the company, Upside combines qualified social workers and housing experts called “care guides” with “housing orchestration” powered by artificial intelligence to provide housing options, case summaries, risk notifications, and more.
“AI is not replacing care guides; it is liberating care guides,” co-founder and chief operating officer Peter Badgley said in a statement. “With repeatable tasks running in the background, our teams can do more of what only humans can do: attend to people in crisis and get them to safety.”
Company executives argue that housing insecurity is one of the most expensive and most-addressed gaps in health care, spanning both the government and commercial sectors. In medical insurance, this is reflected in insurance claims. Despite $9.3 billion in inpatient costs nationwide, most insurance plans still value activity over outcome. Employers know this from their workforce data. Workers who lose their homes are 11 to 22 percentage points more likely to lose their jobs.
The company says its care model has an enrollment rate of over 90%, more than half of members stabilize within 90 days, and a return on investment of up to 4x over 12 months. The platform has expanded rapidly over the past 18 months, partnering with more than 17 state and local health plans and encompassing four of the nation’s largest payers.
The Series A round will fund leadership recruitment and operational depth, including care guide capabilities, partner operations and care model oversight, executives said. Upside also continues to invest in a technology platform that combines proprietary AI workflows for severity stratification, housing matching, and case management with a human-first delivery model.
