Upside, a nationally scalable housing stability platform built for healthcare, raised a $20 million Series A led by Aquiline Capital Partners, with participation from Flare Capital Partners and existing investors. The capital will support Upside's expansion across Medicaid, Medicare Advantage, and employer-sponsored benefits markets, and its continued investment in an AI-supported platform for housing matching and case management.

Exbo Group provided strategic financial diligence on the deal, focusing on revenue quality, gross profit margins, and future cash flow and run rate.

Dante La Ruffa, Partner and Head of Aquiline's Venture & Growth Strategy, said, "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."