Upside Names Brian Lichtlin Chief Technology Officer

The veteran healthcare technology executive, formerly CTO at MDLIVE, joins Upside to lead engineering as the company scales its housing stability platform.

FORT LAUDERDALE, FL — Upside, a nationally scalable housing stability platform purpose-built for healthcare, today announced that Brian Lichtlin has joined the company as Chief Technology Officer. Lichtlin brings more than two decades of healthcare technology leadership, most recently as Chief Technology Officer at MDLIVE, where he led the development and scaling of a telehealth platform that became a market leader and was acquired by Cigna. He will lead Upside’s engineering and technology strategy, scaling the AI-supported orchestration behind its Care Guide model.

Lichtlin joins as Upside expands its work with health plans and employers addressing housing instability across Medicaid, Medicare Advantage, and D-SNP populations. The company’s model pairs dedicated Care Guides with technology that identifies members at risk and coordinates their path to stable housing — a system that has to hold up as the company grows. Lichtlin’s background in telehealth, value-based care, interoperability, and AI-driven healthcare positions him to build that infrastructure at scale.

“Brian and I worked together at MDLIVE, so I have watched him build,” said Chuck Hector, Chief Revenue Officer of Upside. “He scaled a telehealth platform into a market leader, and Cigna acquired it. What we do at Upside gets complicated fast — you are placing high-acuity members in housing before an eviction or a hospital stay turns into a crisis, and the technology has to hold up under that weight. Brian builds systems that do. That is exactly what we need as we grow.”

Before joining Upside, Lichtlin was Co-Founder and CEO of PRO Certified Healthcare and earlier founded and served as CEO of Medappz, a healthcare technology company acquired by Greenway Health. He has also held senior leadership roles across the healthcare technology sector, including Chief Executive Officer of Advalent Corporation and Chief Technology Officer of Synzi. He studied at Hawaii Pacific University.

“I have spent two decades building healthcare technology, and the pattern is always the same: the technology only matters if it makes care work better for real people,” said Brian Lichtlin, Chief Technology Officer of Upside. “Housing is one of the biggest unsolved problems in that equation. Upside pairs Care Guides with technology that helps them stabilize members at scale, and that is exactly the kind of work I want to be building.”

Lichtlin’s appointment reflects Upside’s continued investment in the technology behind its model as it scales. As more health plans turn to housing as a lever for better outcomes and lower cost, Upside is building the engineering depth to meet them — helping members solve housing problems to completion so the lease gets signed and the ER visits stop.

About Upside

Upside is a nationally scalable housing stability platform purpose-built for healthcare. The company partners with health plans and employers to proactively identify and stabilize members and employees experiencing housing instability — connecting them to safe, supportive housing while reducing avoidable emergency care utilization and improving health outcomes. Upside’s model combines dedicated Care Guides — licensed social workers and housing specialists — with AI-supported housing orchestration to deliver measurable results at scale. The platform serves Medicaid, Medicare Advantage, D-SNP, commercial, and employer-sponsored populations across the full housing continuum, from crisis intervention to long-term tenancy support. Founded in 2020 and headquartered in Fort Lauderdale, FL, Upside is redefining how healthcare organizations address housing as a foundation of care. For more information, visit www.joinupside.com.