Upside announced that it raised $20 million in Series A funding to scale its housing stability platform for healthcare. The round was co-led by Aquiline and Flare Capital Partners, with participation from existing investors including 645 Ventures, Freestyle Capital, Triple Impact Capital, and Techstars.
Upside plans to use the funding to accelerate national expansion, build out go-to-market capabilities across health plans and employers, and deepen investment in its AI-supported delivery platform.
The company is focused on addressing housing instability as a major driver of healthcare costs and workforce disruption. Upside said housing instability contributes to $9.3 billion in inpatient costs nationally, while workers who lose their homes are 11 to 22 percentage points more likely to lose their jobs.
Upside was built as a nationally scalable housing stability platform purpose-built for healthcare. The company operates across 10 states and pairs dedicated Care Guides with AI-supported housing orchestration.
The platform is powered by a proprietary affordable housing inventory database that includes public and non-public data. Upside uses this system to identify, engage, and stabilize members before housing challenges become medical crises.
Upside said its care model delivers more than 90% enrollment, stabilizes more than half of members within 90 days, and can generate up to 4x ROI in 12 months.
Over the past 18 months, the company has expanded rapidly, securing partnerships with more than 17 national, state, and regional health plans. Upside is also now supporting four of the largest national payers.
The Series A funding will support Upside’s expansion across Medicaid, Medicare Advantage, and employer-sponsored markets. The company said its employer benefit model can support housing navigation, rental and mortgage support, elder transition planning, and deposit assistance.
Upside also plans to use the funding for leadership hires and operational expansion, including Care Guide capacity, partner operations, and care model oversight.
The company will continue investing in AI workflows for acuity stratification, housing matching, and case management. Upside said its model uses AI to handle repeatable tasks such as surfacing housing options, summarizing cases, and flagging risk, while Care Guides focus on complex relationship-driven work.
Since 2020, Upside has stabilized members across major healthcare lines of business, including D-SNP, Medicaid, commercial, and employer-sponsored populations.
As part of the investment, Aquiline’s Avery Klinger will join Upside’s Board of Directors along with Dan Gebremedhin of Flare Capital Partners.
KEY QUOTES:
“Housing is the highest-cost social problem in healthcare, and most solutions stop at the referral. 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.”
Jake Rothstein, Co-Founder and CEO of Upside
“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. 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.”
Dante La Ruffa, Partner and Head of Aquiline’s Venture & Growth Strategy
“The Health Related Social Needs solutions market is approaching the mid-innings of maturity. The first wave saw companies find success with population-wide screening and solutions directories, but stopped short of driving or guaranteeing outcomes. What drew us to Upside was the rapid cycle time of referral to engagement to success in closing key needs gaps, starting with housing, in a matter of months. We look forward to partnering with the company to further deploy AI technologies to ensure this valuable service is cost-effective and can be deployed to more populations with proven medical and benefit design ROI.”
Dan Gebremedhin, MD, Partner at Flare Capital Partners
“AI does not replace a Care Guide. It frees one up. 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.”
Peter Badgley, Co-Founder and COO of Upside
