Flare Capital Partners is excited to share our investment in Upside’s $20 million Series A financing. Upside is a technology-enabled housing platform that partners with payers, providers, and employers (“risk-bearing entities”) to identify, engage, and stabilize housing-insecure members. We believe Upside is building the infrastructure that transforms one of the most basic needs into a measurable, contractible lever for member engagement, benefit optimization, and medical cost management.
Why We Are Excited
Housing instability is one of the most well-documented root causes of preventable medical spending in the United States. Individuals facing housing insecurity often experience higher rates of emergency department use, preventable inpatient admissions, and gaps in care that compound over time. This impacts both Medicaid and Medicare programs and remains highly relevant for health plans, health systems, and employers. These risk-bearing entities, however, have historically lacked a scalable technology-enabled way to meet housing-insecure patients where they are.
Despite all the national attention that housing issues receive around affordability, housing has often been treated as a social issue that sits outside of the medical system rather than as a measurable cost driver. Once housing is stabilized, however, downstream health-related social needs can be addressed, utilizing housing as a foundational pillar for addressing the Health Related Social Needs (HRSN) market, which is expected to grow to $44.0 billion by 2032.
Peer-reviewed studies continue to signal the size of the opportunity. A recent study published in Health Affairs found that housing support saved $3,260 (roughly $271 per member per month) over a 12-month period, which represents a sizeable opportunity for companies like Upside that can execute on achieving key outcomes.
Why Now
Flare Capital has been investing in healthcare technology companies for over a decade, and we have increasingly built conviction that the intersection between HRSN and healthcare is real, and there is a pressing need to build solutions to fill this poorly understood and opaque gap. We first met the Upside team, and CEO Jake Rothstein, in 2023 and were immediately impressed with their vision to define a new benefit category. We stayed close to Jake as the business matured from an early concept into a scaled operating platform with national and regional health plans contracted across the country. As the posture towards Medicaid funding changed in the 2024 election, there was significant doubt that HRSN solutions and businesses serving the Medicaid market could flourish. Jake and team have grown the business despite perceived headwinds, which speak to the unmet need in this market space and the identification of product-market fit.
Several structural forces are converging in today’s market that are moving housing-based interventions beyond isolated pilots:
- Adoption is cutting through regulatory headwinds: The important signal is that plans are adopting housing navigation services and expanding beyond traditional navigation into downstream drivers of health. Despite perceived regulatory headwinds and temporary funding requirements that require two- or four-year renewals (e.g., HR1, 1115 waivers), demand persists outside of waivers and through Medicaid budget pressure, with health plans anchoring adoption in need and ROI rather than policy tailwinds
- Overwhelming market and member engagement: Engagement in housing-related initiatives across large markets is already exceeding budget. Demand for Upside services in multiple markets is already outstripping their assigned budgets, making this an important time to double down on ROI that drives staff efficiency and can meaningfully reduce total cost of care
- Increasing cost pressures: As medical costs rise and administrative budgets tighten, especially across government programs, risk-bearing entities are under growing pressure to manage total cost of care and optimize existing admin spend. Prevention strategies with measurable ROI that drive engagement for hard-to-reach populations and improve the efficiency of internal case managers are moving up the priority list
- Capital is following suit: Major national health plans and health systems, including UnitedHealth Group, CVS Health Aetna, Kaiser Permanente, and Centene most recently announced housing-related commitments totaling over $1.0 billion in aggregate, reflecting a broader shift toward investment in housing as part of the medical cost equation
- AI workflow makes the model scalable: Intake, eligibility routing, housing matching, and follow-up are all well suited AI use cases within historically labor-intensive workflows. Advancements in artificial intelligence that automate and accelerate these steps while preserving the human relationships that drive trust and engagement are a critical tool for risk-bearing entities
Why Upside
In only 18 months of live commercialization, the company has achieved significant proof points and has experienced broad adoption. The company is live in 10 states and has signed 20 health plans, including four of the largest national managed care organizations in the country. The company delivers several solutions for their health plan partners including member outreach and engagement, housing resource navigation, stabilization support, flex fund account management, and measurement and reporting of outcomes back to healthcare teams.
The platform is designed as a closed-loop, AI-enabled operating system for case managers, combining AI-enabled workflows with humans in the loop to maintain the trust, judgment, and documentation required for complex cases. Upside leverages proprietary data assets that enable better placement rates and stronger adherence to each member’s housing needs.
Upside’s early operating metrics are impressive and suggest the company is performing best-in-class across risk-bearing vendors: Upside connects with over 90% of eligible members, enrolls over 85% of connected members, and drives housing stabilization of roughly 50% of eligible members. Across Medicaid programs specifically, the company reports that more than 80% of members are successfully stabilized.
The Purpose-Built Team
HRSN facing healthcare is a difficult category to build in. It requires navigating complex regulatory landscapes, operational depth and credibility, and fluency across Medicaid and Medicare Advantage economics, all while delivering measurable outcomes across local markets.
Upside’s team is purpose-built for this combination. Together they represent a rare combination of payer social care experience, operational rigor, and deep industry knowledge.
CEO and Co-Founder Jake Rothstein spikes at the intersection of social care, payer-funded services, and large-scale healthcare operations. Jake previously co-founded Papa, the companion care and social support platform that scaled across Medicaid and Medicare Advantage, giving him firsthand experience with the economics of payer-funded social care, the sales cycles required to land and expand within national health plans, and the operational discipline needed to manage a distributed care workforce.
COO and Co-Founder Peter Badgley brings the operational backbone, drawing on his prior experience across operations, real estate, and capital markets. The team also includes seasoned operators, such as Chuck Hector, Chief Revenue Officer, whose deep expertise in partnering with large healthcare enterprises was honed at companies such as MD Live, Papa, and Welltok. The company also has a deep and growing advisor bench that includes regulatory, technology, and real estate expertise.
Looking Ahead
Upside Health is deepening health plan, health system, and employer relationships while extending its platform to serve a broad set of health-related social needs. At Flare Capital Partners, we believe the next era of healthcare infrastructure will be defined by the ability to turn social and behavioral drivers of health into measurable, manageable medical outcomes. Upside exemplifies that shift, and we could not be prouder to partner with Jake and the Upside team as they build it.
For those interested in learning more about its housing stabilization and broader cost management tools, Jake and the Upside team can be
To learn more about Upside: reach out to Dan Gebremedhin (dan@flarecapital.com), Jon George (jon@flarecapital.com) or any member of the Flare Capital Partners team. We would love to hear from you.
Read the original announcement here.
The Upside team is growing! Please see open roles here.
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About Flare Capital Partners
Flare Capital Partners is the leading healthcare technology venture capital firm advancing innovation-driven companies to improve positive health outcomes, broaden care access, and lower healthcare costs. We partner with exceptional founders solving healthcare’s hardest challenges, supporting each with our deep sector expertise, unparalleled industry resources, and proven access to commercial opportunities. Our team of established investors and senior operating executives has invested in 80+ companies and has nearly $1 billion in assets under management. Learn more at www.flarecapital.com.
