Upside
United States, Fort Lauderdale, Florida
About Upside
Upside is a nationally scalable housing-stability platform built for healthcare, partnering with health plans and employers to identify and stabilize members and employees facing housing instability while reducing avoidable emergency utilization. The company pairs dedicated Care Guides (licensed social workers and housing specialists) with AI-supported housing orchestration and a proprietary affordable-housing inventory database, serving Medicaid, Medicare Advantage, D-SNP, commercial, and employer-sponsored populations. Founded in 2020 and based in Fort Lauderdale, Florida, Upside operates across 10 states and works with more than 17 national, state, and regional health plans.
Latest Funding
Series AAnnounced 2026-06-25
Buying Signals
Where the capital is going, and whether it's already started moving.
Spend Intent
4 signals · where the capital is going
Accelerating national expansion, deploying capital simultaneously across Medicaid, Medicare Advantage, and employer-sponsored markets, including a new push into…
prnewswire.com
Funding leadership hires and operational depth, including Care Guide capacity, partner operations, and care-model oversight to scale delivery without compromise…
prnewswire.com
+2 more capital deployment signals · confidence ratings · source articles
Sign up freeHiring Signals
5 open roles · capital meeting headcount
Funding round explicitly earmarked for talent acquisition
R&D spend declared but no engineering hires; possibly outsourcing or tooling
+3 more hiring signals · full department matrix · role-by-role drill-down
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Investors
Freestyle VC
Lead investor · Series A
Tech Stack
HSTS
MySQL
Cloudflare Bot Management
Key Highlights
AI Insights$20M Series A co-led by Aquiline and Flare Capital Partners, with participation from existing investors 645 Ventures, Freestyle Capital, Triple Impact Capital, and Techstars.
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