Open roles at Upside
Latest Upside Signals
What they do
Upside has raised $20 million in Series A financing led by Aquiline, with participation from Flare Capital Partners and others. The funding will be used to expand its AI-enabled housing support platform and enhance partnerships in Medicaid, Medicare Advantage, and employer-sponsored health markets.
Why it matters
Upside has developed a housing stability platform that combines licensed social workers and housing specialists, known as Care Guides, with an AI-supported technology platform. This approach helps identify and stabilize individuals experiencing housing insecurity, addressing a critical social determinant of health.
Traction
Upside has achieved over 90% enrollment rates, with more than half of its members stabilizing their housing within 90 days. The company currently operates in 10 states and has established partnerships with over 17 health plans, including four of the largest payers in the nation.
Where the market is going
Housing instability is a significant driver of avoidable healthcare costs, and Upside's model directly addresses this issue by providing a comprehensive solution that goes beyond mere referrals. By integrating human care coordination with AI-driven operational efficiencies, Upside is poised to disrupt traditional healthcare models that overlook the importance of stable housing.
Why Upside is hiring
Upside closed a $20M funding round in June 2026, with investors including Aquiline, Flare Capital Partners, 645 Ventures and others. It currently has 21 open roles, 7 of them posted in the last 30 days, with hiring concentrated in Austin, DC and New York.
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Upside jobs: common questions
Is Upside hiring?
Yes. Upside has 21 open roles on SuperAIJobs right now, including 7 posted in the last 30 days. The list is refreshed daily from Upside’s own careers site.
Where are Upside jobs located?
Most open roles at Upside are in Austin, DC, New York and NYC. 4 roles are listed as remote or remote-friendly.
Does Upside hire remotely?
Yes — 4 of Upside’s 21 open roles mention remote work. Check each listing for the countries or time zones it covers.
How much has Upside raised?
The latest round we track is a $20M funding round in June 2026. Investors include Aquiline, Flare Capital Partners, 645 Ventures and others. See the full deal history on MapCo.
What does Upside do?
Upside has developed a housing stability platform that combines licensed social workers and housing specialists, known as Care Guides, with an AI-supported technology platform.
How do I apply for a job at Upside?
Every role on this page links straight to Upside’s own application page, so you apply directly — SuperAIJobs never sits in between.