Upside Raises $20M in Series A Funding Led by Aquiline 

The round also saw participation from Flare Capital Partners, 645 Ventures, Freestyle Capital, Triple Impact Capital and Techstars. As part of the investment, Aquiline’s Avery Klinger will join Upside’s Board of Directors along with Dan Gebremedhin of Flare Capital Partners.

The company plans to use the funding to speed up its expansion across the country, strengthen its sales and go-to-market efforts with health plans and employers, and further develop its AI-powered platform.

Upside’s care model is designed as an employee benefit that supports housing needs, including finding housing, help with rent or mortgage payments, planning for elder care transitions, and assistance with deposits.

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Upside operates across 10 states, combining dedicated Care Guides with AI-powered housing support. It uses a proprietary housing database that includes both public and private listings to help identify, engage, and stabilize members before housing issues become health crises.

The model has strong results, including over 90% enrollment, more than half of members stabilized within 90 days, and up to 4x ROI within a year. It also reports high member satisfaction.

In the past 18 months, Upside has expanded quickly, partnering with more than 17 health plans and now working with four of the largest national payers. Co-founder and CEO Jake Rothstein said the company goes beyond referrals by placing people into stable housing and helping them stay housed, and that new funding will help scale this impact more broadly.

Housing instability is one of the most costly and solvable problems in healthcare, affecting both government programs and private employers.

Health plans see the impact through claims, with $9.3 billion in inpatient costs nationwide, but many still focus on tracking activity instead of outcomes. Employers see it in workforce data, where employees who lose housing are 11–22% more likely to lose their jobs, and high healthcare costs often come from the same individuals facing housing issues. Both are dealing with the same underlying problem and need a single partner to address it fully.

"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."

"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," said Dan Gebremedhin, MD, Partner at Flare Capital Partners.

"AI does not replace a Care Guide. It frees one up," said Peter Badgley, Co-Founder and COO of Upside. "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."

About Upside

Founded in 2020 by Jake Rothstein and Peter Badgley, Upside is a housing stability platform built for healthcare. The company works with health plans and employers to help people facing housing instability find and keep stable housing while improving health outcomes and reducing avoidable healthcare costs. Upside combines dedicated Care Guides, including licensed social workers and housing specialist's with an AI powered housing platform to deliver personalized support at scale.

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