A practical housing partner for health plans and employers.
Upside began with a personal experience that many families know well. Jake Rothstein, our founder, watched his grandmother Margarita struggle to remain safely housed as she aged. She didn’t need institutional care. She needed the right living situation — one that fit her mobility, health, and independence. What was missing wasn’t care. It was housing support that actually worked.
As we tried to help families like hers directly, a larger pattern became clear: housing instability wasn’t an edge case. It was everywhere. And there was no system built to handle it. So we built one.
Upside is a housing-first organization focused entirely on stabilization, transitions, and long-term housing fit. We work alongside health plans and employers when housing becomes the barrier — blocking engagement, driving utilization, or disrupting work and care. Once engaged, we take responsibility for the housing work itself, so internal teams don’t have to manage the time-intensive, local complexity. This includes everything from assessment to coordination to follow-through, with clear visibility and accountability throughout.
We help you lead with housing—and prove it works.
We understand the pressures health plans face: to lower costs, improve performance metrics, and serve members better. Upside supports those goals by making housing a measurable, scalable part of your strategy—built to flex across Medicaid, Medicare Advantage, C-SNP and D-SNP populations.
Not a vendor. A housing partner.
Upside isn’t a tech layer or a case management add-on—we’re a fully operational housing infrastructure partner. With flexible contracting, tailored eligibility criteria, real-time vacancy tracking, and fully accountable Care Guides, we embed directly into your plan’s operations to make housing seamless and strategic. We’ve built the processes, relationships, and systems to move fast—without sacrificing personalization or performance.
We help you lead with housing—and prove it works.
We understand the pressures health plans face: to lower costs, improve performance metrics, and serve members better. Upside supports those goals by making housing a measurable, scalable part of your strategy—built to flex across Medicaid, Medicare Advantage, and D-SNP populations.
Jake Rothstein
Co-Founder & CEO
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 Badgley
Co- Founder & COO
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’s passionate about creating housing solutions that advance health equity nationwide.
Chuck Hector
Chief Revenue Officer
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. His work ensures vulnerable populations can stabilize their living situations and refocus on health, family, and recovery.
Julie Isaacs
Vice President of Care Operations
Julie is a licensed clinical social worker and healthcare leader with over a decade of experience improving care systems and scaling behavioral health operations. At Upside, she leads care delivery with a focus on clinical excellence, team development, and human-centered design. Julie brings empathy, structure, and strategic vision to ensure both patients and staff thrive.
Patrick Regan
Executive Vice President of Sales
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. Patrick is a collaborative leader focused on growth, innovation, and long-term impact.
Megan Wagner
Vice President of Partner Operations
Megan leads partner operations at Upside with a sharp focus on efficiency, scalability, and long-term success. She brings deep experience in launching and optimizing programs for health plans, ensuring seamless service delivery and strong partner outcomes. Known for her clear communication and problem-solving skills, Megan is a key driver of Upside’s mission to make housing stability accessible and effective.
Todd Michalik
Vice President of Technology
Todd leads product and technology at Upside, guiding innovation from concept to launch with a focus on real-world impact. He brings deep experience in building high-performing teams and delivering scalable, user-centered solutions. Todd’s leadership ensures Upside’s platform remains at the forefront of housing stability innovation.
Spencer Smith
Vice President of Marketing
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. His work bridges strategy and storytelling to elevate Upside’s mission and market presence.
Lawrence Leisure
Advisor
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 the Co-Founder and Managing Partner of Chicago Pacific Founders and has guided organizations ranging from global consulting firms to high-growth startups toward better care delivery at lower cost. Larry has co-founded multiple influential healthcare platforms, including Healthspottr and the Employer Health Innovation Roundtable, and served as Co-Founder and Chairman of ADVI’s Reimbursement and Health Policy Advisory Services. His career includes senior leadership roles at Accenture, Kleiner Perkins, and other industry-defining organizations, where he has consistently brought together top talent, transformative ideas, and strategic capital to drive lasting impact in healthcare.
Daniel Hoemke
Advisor
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—skills that help Upside position housing as a lever for both cost containment and improved member outcomes. Known for his ability to turn around underperforming organizations and build high-performing teams, Daniel has guided health plans through complex market shifts while keeping focus on what matters most: better health for members. At Upside, he advises on growth strategy and payer engagement, ensuring our housing solutions align with the operational, financial, and regulatory realities health plans face today.
Jason Parrott
Advisor
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 in adopting innovative approaches to improve workforce health and manage costs. Jason also brings deep governance experience as a board member and advisor to leading health and benefits organizations, including the Employer Health Innovation Roundtable. At Upside, he advises on employer and payer engagement strategies, helping position housing stability as a core component of health and workforce resilience.
Dr. Elissa Kozlov
Advisor
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 through research, education, and advocacy. With a Ph.D. in clinical and aging psychology and a Beeson K76 Award, she brings critical expertise to Upside’s mission.
Aaron Holiday
Board Member
Aaron is the 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 brings deep expertise in technology, finance, and high-growth company building. He also serves on the Cornell Tech governing board and was named to the Midas Brink List for his track record of early-stage investment success.
What is a Housing Stability Program?
A Housing Stability Program is a structured, outcomes-focused approach to identifying, addressing, and resolving housing-related risks for vulnerable members. Upside delivers the first national platform built specifically for health plans—combining proactive screening, rapid placement, and ongoing support to improve outcomes and reduce avoidable spend.
How is Upside different from Community-Based Organizations (CBOs)?
CBOs do important work—but they’re often hyperlocal, fragmented, and stretched thin. Upside offers a fully managed, nationwide solution that replaces fragmented referrals with real placements. Our Care Guides don’t hand off—they handle. And our network includes everything from affordable housing to class A units, tailored by need and geography. We integrate, we scale, and we deliver outcomes.
Can Upside support multiple populations?
Absolutely. Upside is built to serve diverse member groups—across Medicaid, Medicare Advantage, D-SNP, and beyond. Our approach flexes to meet different needs, eligibility criteria, and geographies. Whether it’s a high-touch senior or a younger member facing a housing crisis, we have the tools and the model to help.
Do you operate in my market?
We work nationally, with a growing network of over 33,000 housing partners and active operations across major regions. Want to know what coverage looks like in your area? Contact us and we’ll walk you through it.
How does pricing work?
Our pricing is flexible, aligned with performance, and customized to your plan. We offer multiple contracting models to fit your goals and scale. Let’s talk about what works for your population and budget.
What ROI can I expect from Upside?
Plans that partner with Upside see measurable reductions in medical costs, improved engagement, higher retention, and stronger satisfaction scores. Housing is one of the few interventions that improves both outcomes and economics—and we make it trackable, scalable, and immediate.
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.
Upside Corporate Headquarters
200 E Las Olas Blvd 14th Floor
Fort Lauderdale, FL 33301
