June 26, 2026, 5:02 PM IST

Upside Bags $20M Series A to Solve the U.S. Housing Crisis for Healthcare

Upside, a housing stability platform partnering with health insurers, raised $20 million in Series A funding. Aquiline and Flare Capital Partners co-led the investment round with support from existing investors including 645 Ventures, Freestyle Capital, Triple Impact Capital and Techstars.

Including the latest round, Upside has raised $30 million to date.

Upside offers an AI-powered platform that helps payers and employers identify members experiencing housing instability and pairs them with social workers and housing specialists. The company can then support them in finding housing, which helps reduce emergency medicine utilization. It serves Medicaid, Medicare Advantage, Dual Eligible Special Needs Plans, commercial and employer-sponsored populations.

The financing will support national expansion, according to the press statement. In addition, it will help scale its government healthcare and self-insured employer lines of business, as well as support investment in its AI infrastructure, said Jake Rothstein, Co-Founder and CEO of Upside.

Currently, housing instability leads to $9.3 billion in inpatient costs nationally, and workers who lose housing are 11 to 22 percentage points more likely to lose their jobs, the announcement stated. This is what Upside ultimately hopes to change.

“Housing is the highest-cost social problem in healthcare, and most solutions stop at the referral,” said Jake Rothstein, Co-Founder and CEO of Upside. “We go beyond that. Upside places people into stable housing and keeps them there. This growth capital means we get to do that for more people, in more markets, more quickly.”

“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 Dante La Ruffa, Partner and Head of Aquiline’s Venture & Growth Strategy. “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.”

As part of the investment, Aquiline’s Avery Klinger will join Upside’s Board of Directors along with Dan Gebremedhin of Flare Capital Partners.

Digital health companies have secured more than $180 billion in funding to date, according to our recent Funding Database. More recently, Connie Health, a provider of an AI-powered Medicare navigation platform, secured $40 million in Series B financing, bringing its total funding to date to $85 million.