Upside, a scalable housing stability platform, banked a $20 million series A funding round to continuing addressing the U.S. housing crisis from a healthcare lens.Â
Aquiline led the round, with participation from Flare Capital Partners and support from existing investors 645 Ventures, Freestyle Capital, Triple Impact Capital and Techstars.
Aquiline Venture and Growth Strategy Head and partner Dante La Ruffa said in a statement housing instability is “one of the most persistent drivers of avoidable healthcare spend.”
“Upside has the model, team, and infrastructure to address it, and we're excited to partner with the company in its next chapter,” said La Ruffa. “We see significant opportunities to accelerate Upside's momentum through Aquiline's strategic connectivity across health plan, payer, and broker channels, as well as through product adjacencies that further expand the company's value proposition for all key stakeholders.’
The company plans to use the funding simultaneously across Medicaid, Medicare Advantage and employer-sponsored markets. It also plans to hire leadership and expand its operational capabilities.
Launched in 2020, Upside was founded by Jake Rothstein and Peter Badgley. Rothstein, who serves as CEO, previously co-founded Papa, which pairs older adults and families with “Papa Pals” for companionship. The company says it is the sole nationally scalable housing stability platform purpose-built for healthcare. It works across 10 states and partners with health plans and employers to identify and stabilize individuals experiencing housing instability—before the situation becomes a medical crisis.
Upside executives say the company's care model translates into a workforce benefit covering housing navigation, rental and mortgage support, elder transition planning and deposit assistance.
Upside pairs licensed social workers and housing specialists—called "care guides"—with artificial intelligence-driven “housing orchestration,” the company says, which includes housing options, summarizing cases and flagging risk.Â
“AI does not replace a Care Guide. It frees one up,” said Peter Badgley, co-founder and COO, in a statement. “When the repeatable work runs in the background, our team can do more of what only people can do, which is sit with someone in crisis and get them somewhere safe.”
Company executives assert that housing instability is one of healthcare's most expensive and most addressable gaps, and it spans both government and commercial lines of business. Health plans see it in claims: $9.3 billion in inpatient costs nationally, yet most still measure activity over outcomes. Employers see it in workforce data: workers who lose their homes are 11 to 22 percentage points more likely to lose their jobs.
The company says its model of care delivers 90+% enrollment, sees more than half of members stabilized within 90 days and delivers up to 4x return on investment in 12 months. The platform has seen rapid expansion over the past 18 months and has partnered with more than 17 state and regional health plans—with four of the largest national payers under its belt.
The series A round will fund leadership hires and operational depth, including care guide capacity, partner operations and care model oversight, executives said. Upside also will continue investing in its technology platform, which combines proprietary AI workflows for acuity stratification, housing matching and case management with a human-first delivery model.