Aquiline led the round with Flare Capital Partners and continued support from existing investors including 645 Ventures, Freestyle Capital, Triple Impact Capital and Techstars. The capital accelerates Upside's national expansion, builds out go-to-market capabilities across health plans and employers, and deepens investment in the company's AI-supported delivery platform. Upside is led by industry veterans who previously built category-defining healthcare companies, including MDLive, Papa, and Virta Health.

Upside is the only nationally scalable housing stability platform purpose-built for healthcare. The company partners with health plans and employers to identify and stabilize members and employees experiencing housing instability, connecting them to safe, supportive housing while reducing avoidable emergency utilization and improving health outcomes. Upside pairs dedicated Care Guides (licensed social workers and housing specialists) with AI-supported housing orchestration to deliver measurable results at scale. The platform serves Medicaid, Medicare Advantage, D-SNP, commercial, and employer-sponsored populations across the full housing continuum, from crisis intervention to long-term tenancy support. Founded in 2020 and headquartered in Fort Lauderdale, FL, Upside is redefining how healthcare addresses housing as a foundation of care.