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.
Housing problems don’t get solved by software alone. They get solved by people who know how to navigate real-world constraints. Upside uses technology to support speed, prioritization, and consistency behind the scenes. But the work itself is led by dedicated Care Guides who build trust, make judgment calls, and follow through until housing is stable. Technology helps us move faster. People make the work possible.
Upside does one thing: housing. We don’t spread attention across dozens of social needs or programs. That focus allows us to understand local housing markets, common barriers, and what actually moves cases forward. By staying narrow, we go deeper — and that’s what produces outcomes.
We don’t measure success by referrals sent or conversations logged. Our work is organized around resolution: whether housing is stabilized, a move is completed, or a transition is safely coordinated. That clarity shapes how cases are worked, how progress is tracked, and how partners understand impact.
Most organizations treat housing as something to coordinate around the edges. Upside treats it as infrastructure. That means clear ownership, repeatable workflows, defined handoffs, and accountability through completion. Housing work doesn’t rely on hope or goodwill. It runs through systems designed to handle volume, variation, and urgency.
Housing shouldn’t be the hardest problem to solve. Upside exists to make housing support predictable, usable, and integrated into how care and workforce systems already function. When housing is handled early and intentionally, everything else works better — engagement, safety, transitions, and outcomes. That’s the standard we’re building toward.
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.
Ryan Walsh
Vice President of Partnerships
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.
Barb Wachsman
Advisor
Barbara is a nationally respected employer health leader with more than 25 years of experience designing and operating high-impact healthcare strategies for large, complex workforces. She previously led Benefits Strategy and Engagement at The Walt Disney Company, where she oversaw a multibillion-dollar healthcare budget, managed onsite clinics and physician partnerships, and pioneered one of the largest full-risk, direct-to-health-system arrangements in the country. Barbara brings deep expertise in employer benefits, primary care transformation, and value-based delivery models. At Upside, she advises on employer strategy and innovation, helping position housing stability as a critical extension of access, affordability, and workforce health—especially for employees facing chronic conditions and systemic barriers to care.
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 kind of organization is Upside?
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. Our role is to manage the practical, local work required to move housing situations forward and see them through to resolution.
How does Upside work with existing teams and partners?
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 and aligned throughout the process.
What types of populations does Upside support?
Upside supports 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, particularly when housing barriers are difficult to resolve through referrals alone.
How is success measured?
Success is measured by whether housing situations move toward stability. Depending on the program, that may include stabilized housing, completed moves, safer living environments, or appropriate transitions. We focus on outcomes and resolution — not just activity or engagement.
How does Upside get involved?
Upside typically works through referrals or targeted engagement, depending on the program. Once involved, we take responsibility for coordinating housing work through completion, while providing clear visibility into progress and outcomes.
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
