From personal experience to national scale—redefining housing as health infrastructure.
Built from lived experience, driven by purpose.
Upside began with a single story—Margarita, our founder Jake’s grandmother, whose housing situation became unsafe as she aged. Like millions of others, she didn’t need a nursing home—she needed the right home. What started as a direct-to-consumer effort to help families like hers quickly revealed a much larger issue: housing instability was everywhere, and the system to solve it didn’t exist. So we built it.
A housing platform designed for health plans.
Today, Upside partners with health plans to provide full-service, population-specific housing solutions. We handle everything from member screening to placement to long-term housing stability. Our platform combines human expertise with real-time data and contracted housing inventory—turning housing from a referral process into a lever for measurable outcomes.
We don’t just identify housing needs—we solve them.
Most programs refer members to overwhelmed community resources and hope for the best. Upside takes full responsibility for placing members quickly, safely, and sustainably. Our Care Guides work one-on-one with each member while aligning with your team’s goals, ensuring outcomes that improve satisfaction, retention, and spend.
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.
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.
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.
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.
Jake Rothstein
Founder & CEO
Jake is a seasoned entrepreneur and investor with over a decade of experience in founding, funding, building, scaling, and managing successful global organizations and teams. He is passionate about solving complex problems and creating positive social impact through innovation and technology.
As the Founder and CEO of Upside, Jake leads the vision and strategy of the company, whose mission is to ‘Humanize Healthcare through Housing.‘
Upside is Housing for Health, offering scalable housing stability programs for health plans and their members nationwide. Our unique approach enables housing stability and security across population types and in environments that meet member’s specific needs. By addressing housing first, we are able to drive utilization on other key social drivers of health and contribute to improved health outcomes, helping payers reduce medical care costs, improve member acquisition and retention and drive member satisfaction.
Peter Badgley
Founder & COO
Upside is Housing for Health, offering scalable housing stability programs for health plans and their members nationwide. Our unique approach enables housing stability and security across population types and in environments that meet member’s specific needs. By addressing housing first, we are able to drive utilization on other key social drivers of health and contribute to improved health outcomes, helping payers reduce medical care costs, improve member acquisition and retention and drive member satisfaction.
I’m grateful to have the opportunity to lead a high-performance team at Upside as the COO. My objective is to serve the team by developing efficient processes, designing effective training programs, and implementing strategies that drive outstanding results. I strongly believe in fostering a positive culture that is built on trust, accountability, giving your best, and continuously improving each day.
Outside of my role, I find immense joy in being a dedicated father to my twin boys and embracing the adventures of parenthood with my wife, Erica.
Julie Isaacs
VP of Care Operations
Julie is a compassionate and purpose-driven leader with a background as a Licensed Clinical Social Worker and more than a decade of experience guiding teams in behavioral health and healthcare. Her career has been shaped by a deep commitment to improving access to care, supporting clinicians, and building systems that truly serve people.
Known for her warmth, steady leadership, and ability to bring calm to complexity, Julie has led high-growth organizations through major transitions, multi-state expansions, and clinical innovation. She’s passionate about building strong, mission-aligned teams and making care delivery more human—while never losing sight of operational excellence.
Whether she’s mentoring a new leader, rethinking a service model, or digging into data to drive meaningful change, Julie brings both heart and discipline to her work. She believes the best outcomes happen when we care for people—patients and staff alike—with empathy and clarity.
Megan Wagner
VP of Partner Operations
Megan Wagner is known for her passion in driving business development and operational efficiency. Her expertise in identifying improvement areas, streamlining processes, and fostering successful partnerships has been crucial in enhancing Upside’s service delivery. Megan excels in clear communication and complex problem-solving, mentoring colleagues across various levels. Her commitment to efficiency and effectiveness significantly contributes to Upside’s mission of providing stable, affordable housing solutions to all members.
In addition to her accomplishments at Upside, Megan has a track record of leadership in planning, implementing, launching, and achieving partnership success in programs for health plans. Her experience in this area further highlights her ability to drive results and create impactful solutions.
Chuck Hector
Chief Revenue Officer
With a history as the Chief Revenue Officer of in-home support company Papa and MDLIVE, a telehealth industry leader, Chuck Hector brings decades of experience in healthcare sales, implementation, and client success. His leadership roles at industry innovators including Circadian Health, IncentOne and ComPsych have equipped him with a deep understanding of health incentives and managed behavioral health, which is pivotal in advancing Upside’s mission.
Patrick Regan
EVP of Sales & GTM
Patrick serves as our EVP of Enterprise Health Care Sales, bringing an impressive 18 years of experience in B2B roles. With a proven track record in revenue growth, Patrick provides strategic guidance and hands-on leadership to our team. His commitment to collaboration, innovation, and client satisfaction at Upside is driven by his personal experience assisting an aging family member facing housing challenges.
Outside of work, Patrick embraces the joys and challenges of parenthood as a dedicated dad (#GirlDad). He also enjoys watching his favorite football team play on Saturdays, passionately supporting the team with a resounding ‘Go Noles!’
Todd Michalik
Head of Product & Tech
Todd Michalik brings a wealth of experience as the Head of Product at Upside, marked by a successful track record in the technology industry. His expertise spans the entire product development lifecycle, from ideation to launch. Known for his strong leadership and communication skills, Todd excels in building and motivating high-performing teams. He is deeply passionate about developing innovative products that address real-world challenges, significantly contributing to Upside’s mission of delivering impactful housing stability solutions.
Todd’s leadership has been instrumental in driving Upside’s product innovation and success. Under his guidance, the company has consistently delivered cutting-edge solutions that have positively impacted the housing stability of countless individuals and communities.
Dr. Elissa Kozlov
Advisor
Dr. Elissa Kozlov, Ph.D. is an NIH-funded, assistant professor in the Department of Health Behavior, Society, and Policy and the Director of the Population Aging Concentration at Rutgers School of Public Health. Dr. Kozlov is a dedicated advocate, educator and researcher for improving healthcare outcomes for older adults and individuals with serious illnesses. Her extensive background in various clinical settings, coupled with her academic achievements, which include a doctoral degree in clinical and aging and developmental psychology from Washington University in St. Louis and a Beeson K76 Career Development Award from the National Institute on Aging, position her as a vital asset to Upside’s mission.
John Gorman
Advisor
John Gorman’s authoritative knowledge in Medicare, Medicaid, and Affordable Care Act strategy comes from a rich history of governance and turnarounds of distressed health plans. Prior to founding Gorman Health Group, he served in significant roles at the Health Care Financing Administration’s (HCFA, now CMS) Office of Managed Care. John’s extensive background in healthcare policy advocacy and government affairs, along with his current advisory roles, makes him a critical advisor for Upside’s innovative housing initiatives.
Dr. Nirav R. Shah
Advisor
As a Senior Scholar at Stanford University’s School of Medicine, Dr. Nirav R. Shah, MD, MPH is a highly respected healthcare leader known for his expertise in public health, healthcare insurance, and clinical operations. He is a Board-certified Internal Medicine specialist and a graduate of Harvard College and Yale School of Medicine. Dr. Shah holds advisory roles at the CDC, serves as a Senior Fellow of the Institute for Healthcare Improvement (IHI), and is an independent director of STERIS plc. He also serves as a trustee of the John A. Hartford Foundation and previously held the position of Chief Operating Officer of Kaiser Permanente in Southern California and Commissioner of the New York State Department of Health. His notable career spans roles as an operator, scientist, innovator, and regulator. Dr. Shah’s ongoing research at Stanford, aimed at enhancing healthcare quality and safety while lowering costs, aligns seamlessly with Upside’s mission to promote health equity through innovative housing solutions.
Upside Corporate Headquarters
200 E Las Olas Blvd 14th Floor
Fort Lauderdale, FL 33301
