Upside Appoints Five Industry Leaders to Executive Advisory Board to Accelerate Innovation in Housing-First Health Care

August 26, 2025

Advisors from Accenture, CPF/EHIR, Cigna, VillageMD, and Vida Health bring payer, provider, employer, and digital health expertise to strengthen Upside’s platform across Medicaid, Medicare Advantage, and employer markets.

Fort Lauderdale, FL – Upside, the only housing stability platform purpose-built for healthcare, today announced the appointment of five nationally recognized healthcare leaders: Lawrence (Larry) Leisure, Julie Mascari, Bryan Hebert, Daniel Hoemke, and Jason Parrott to its Executive Advisory Board. Together, they bring more than a century of experience spanning value-based care, payer innovation, government programs, provider relations, and healthcare technology.

The appointments come at a pivotal time for Upside, as demand accelerates for scalable, accountable housing solutions that directly support clinical performance, member retention, and total cost-of-care reduction across Medicaid, Medicare Advantage, commercial plans, and self-insured employers.

“Larry, Julie, Bryan, Daniel, and Jason are among the most respected and forward-thinking leaders in healthcare,” said Jake Rothstein, Founder and CEO of Upside. “They’ve built transformative organizations, shaped industry standards, and challenged conventional thinking to improve care for diverse populations. Their guidance will be invaluable as we deepen our partnerships with health plans and employers nationwide and scale a model that delivers measurable impact for both members and payers.”

• Lawrence (Larry) Leisure is Co-Founder and Managing Partner at Chicago Pacific Founders and co-founded ADVI’s Reimbursement and Health Policy Advisory Services, Healthspottr, and the Employer Health Innovation Roundtable (EHIR). A former Global Managing Partner of Health Services at Accenture and senior advisor to Kleiner Perkins, Larry has guided organizations at the forefront of managed care, life sciences, and digital health, advancing better care at fairer prices and consistently delivering both patient benefit and investor value.
• Julie Mascari is a seasoned healthcare executive with 25+ years of leadership across government programs and multi-line operations. Most recently, she led a provider-founded company focused on reducing medical expenses in Black, Brown, and rural communities. Julie has driven multi-million-dollar revenue growth while building competency frameworks, redesigning organizations for agility, and forging high-performing cultures in fast-changing markets.
• Bryan Hebert brings deep experience across payer, provider, technology, and BPO sectors, spanning sales, operations, and IT in commercial and government programs (including Medicaid, Medi-Cal, Medicare, and self-funded employers). He has led teams in risk adjustment, value-based contracting, telehealth, care coordination, claims, and AI-driven predictive health. Bryan currently advises AI startups in medical necessity, denial management, and predictive healthspan modeling, leveraging regulatory and operational expertise to improve outcomes and cost efficiency.
• Daniel Hoemke brings more than 30 years of leadership across Commercial and Government health segments. He most recently served as SVP of Growth and Western Region President at VillageMD, where he drove Medicare expansion and held full P&L accountability across multiple markets. Previously, he was Market President for Cigna Medicare Desert States (AZ/NV), leading distribution, performance, and member growth. Daniel is recognized for delivering results in value-based care and risk contracting and now serves as a strategic advisor to VillageMD, supporting business development and Medicare growth.
• Jason Parrott is SVP of Enterprise Growth & Partnerships at Vida Health, where he leads large-scale growth initiatives and strategic partnerships for the digital health leader. Previously, he directed healthcare and well-being strategy at Boeing and held progressive leadership roles at AT&T in HR and benefits strategy. Jason brings over two decades of expertise in distribution, growth, and benefits innovation and has served on the boards of the Employer Health Innovation Roundtable, the Integrated Benefits Institute, and the Midwest Business Group on Health.

“Upside is tackling one of the most urgent and overlooked challenges in healthcare: housing stability, with a level of scale, accountability, and payer alignment that’s unprecedented,” said Larry Leisure. “I’m honored to help guide its next phase of growth.”

“The model directly addresses disparities that persist in underserved communities,” said Julie Mascari. “It’s an opportunity to align compassion with measurable financial outcomes.”

“Upside understands that housing is a care delivery asset,” said Bryan Hebert. “I look forward to helping optimize payer partnerships and operational models that deliver lasting value.”

“Upside is reimagining housing as a critical lever in value-based care,” said Daniel Hoemke. “I look forward to contributing my experience in Medicare and growth strategy to help scale its impact nationally.”

“Housing-first strategies like Upside’s are game-changers for population health,” said Jason Parrott. “I’m excited to bring my experience in employer partnerships and virtual care growth to help scale this impact.”

About Upside

Upside is the only fully managed housing stability platform built specifically for health plans and self-insured employers. Designed to improve outcomes and reduce costs, Upside provides scalable, accountable housing solutions for Medicaid, Medicare Advantage, D-SNP, commercial, and employer-sponsored populations. From housing assessments and placement to tenancy support and performance analytics, Upside delivers end-to-end infrastructure that aligns social needs with clinical outcomes. With national reach and proven ROI, Upside is redefining how healthcare organizations address housing as a foundation of care.

For more information, visit www.joinupside.com and follow us on LinkedIn.

Media Contact:
Spencer Smith
ssmith@joinupside.com