Upside exists to solve one problem well: housing instability that disrupts health, care, and outcomes at scale.
Upside began after our founder watched a family member’s housing become unsafe — not because of medical need, but because the environment no longer fit her life. The challenge wasn’t clinical. It was practical, local, and hard to navigate.
That experience revealed something bigger: housing instability was widespread, deeply tied to outcomes, and addressed through fragmented efforts that rarely carried cases to resolution.
There was no infrastructure designed to handle housing the way complex needs are handled elsewhere. So we built it.
Upside is built to do the housing work most organizations can’t staff for. We accept referrals or outreach, assess housing needs, execute stabilization or transitions, and stay involved until the issue is resolved. That includes navigating local constraints, coordinating with community partners, managing logistics, and documenting outcomes plans can stand behind.
We don’t stop at identification or referral. We carry housing cases to resolution.
Jake is a seasoned entrepreneur focused on building mission-driven companies that solve complex social challenges. As CEO of Upside, he leads strategy and growth to deliver scalable housing solutions that improve health outcomes and reduce healthcare costs. His work bridges innovation, housing, and healthcare to drive measurable impact for payers and their members.
Peter drives operations at Upside, building the systems and processes that enable scale, efficiency, and high-quality service delivery. He leads with a focus on team development, operational excellence, and a culture rooted in trust and continuous improvement. As a co-founder, he is passionate about creating housing solutions that advance health equity nationwide.
Chuck leads Upside’s go-to-market strategy, connecting health plans with scalable housing solutions that address one of healthcare’s toughest challenges: housing instability. He helps payers support members in crisis through a national housing network and hands-on case management services.
Todd leads technology and platform strategy at Upside, ensuring the infrastructure, data, and systems behind the product can scale to meet the complexity of housing at a national level. He brings deep experience building high-performing teams and delivering user-centered solutions that operate reliably in real-world environments.
Brian leads technology strategy and innovation at Upside, bringing more than two decades of experience building and scaling healthcare technology platforms. He previously served as CTO of MDLIVE, which he helped grow into a market-leading telehealth platform prior to its acquisition by Cigna, and founded Medappz, acquired by Greenway Health. His expertise spans AI-driven solutions, interoperability, and value-based care infrastructure.
Megan leads partner operations at Upside with a sharp focus on efficiency, scalability, and long-term success. She brings deep experience launching and optimizing programs for health plans, ensuring seamless service delivery and strong partner outcomes.
Dr. Arora brings a physician’s perspective to the design and delivery of Upside’s housing stability programs, ensuring they are grounded in real-world patient needs and operational excellence. With a background in digital health, product strategy, and program management, she leads clinical care operations with a focus on scalable, patient-centered systems.
Austin leads operations across the full member journey at Upside — from referral and engagement through housing stabilization and ongoing support. He ensures the program delivers timely, coordinated, and high-quality experiences at scale, translating strategy into execution.
Patrick brings 18 years of B2B experience to his role leading enterprise healthcare sales at Upside, with a strong record of driving revenue and building client partnerships. His personal connection to housing challenges fuels his passion for delivering solutions that improve lives.
Ryan leads Upside’s health plan partnerships, forging strategic collaborations that help health plans address housing as a critical driver of health. Drawing on his background as a licensed attorney and years of experience building innovative partnerships across healthcare, he helps organizations navigate complexity, align incentives, and ensure more people have the stability of a home—the foundation upon which better health is built.
Spencer leads Upside’s marketing strategy, positioning the company as a trusted partner for health plans tackling housing instability. He drives awareness, adoption, and national distribution by highlighting the platform’s impact and human stories.
Larry is a veteran healthcare leader and investor with over 40 years of experience shaping the future of managed care, health technology, and employer health innovation. He is Co-Founder and Managing Partner of Chicago Pacific Founders and has co-founded multiple healthcare platforms, including Healthspottr and the Employer Health Innovation Roundtable. His career includes senior leadership roles at Accenture and Kleiner Perkins.
Advisor
Barbara is a nationally respected employer health leader with more than 25 years of experience designing high-impact healthcare strategies for large, complex workforces. She previously led Benefits Strategy and Engagement at The Walt Disney Company, overseeing a multibillion-dollar healthcare budget and pioneering one of the largest full-risk, direct-to-health-system arrangements in the country.
Daniel is a proven healthcare leader with more than 30 years of experience driving growth and transformation across commercial and government health plans. He brings deep expertise in value-based care, provider contracting, and benefit design.
Jason is a nationally recognized leader in employer health strategy, with more than 25 years shaping benefits design, well-being programs, and large-scale partnerships. As SVP of Growth and Partnerships at Vida Health and former head of Healthcare & Well Being Strategy at Boeing, he has guided some of the country’s largest employers.
Dr. Kozlov is an NIH-funded researcher and assistant professor at Rutgers School of Public Health, where she directs the Population Aging Concentration. Her work focuses on improving healthcare outcomes for older adults and people with serious illnesses.
Aaron is co-founder and Managing Partner of 645 Ventures, where he leads investment strategy and has backed breakout startups like Goldbelly, Iterable, and FiscalNote. A former software engineer at Goldman Sachs, he serves on the Cornell Tech governing board.
Upside is a housing partner that takes ownership of housing stabilization work end to end. We’re not a referral directory, a technology add-on, or a general social services provider.
Upside works alongside internal teams and community partners. We don’t replace care management, benefits teams, or CBOs. We take on the time-intensive housing work they aren’t designed to carry, while keeping all stakeholders informed.
Individuals whose housing situations are complex, unstable, or no longer appropriate — and where that instability disrupts health, care, or work. This includes members and employees across Medicaid, Medicare, and employer settings.
By whether housing situations move toward stability: stabilized housing, completed moves, safer living environments, or appropriate transitions. We focus on outcomes and resolution — not just activity.
Typically through referrals or targeted engagement. Once involved, we take responsibility for coordinating housing work through completion, with clear visibility into progress.
Plans that partner with Upside see measurable reductions in medical costs, improved engagement, higher retention, and stronger satisfaction scores.
Let's talk about how Upside can help your plan reduce spend, improve outcomes, and deliver real stability to the members who need it most. Whether you're exploring a pilot or looking to scale, we're ready to build a solution that fits.
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