June 1, 2026
Veteran customer success leader brings more than a decade of health-tech experience to Upside as the company scales its housing stability programs across Medicaid, Medicare Advantage, and employer markets.
FORT LAUDERDALE, FL — Upside, a nationally scalable housing stability platform purpose-built for healthcare, announced today that Alexandra Earl has joined the company as Senior Vice President of Client Success. Alex brings more than a decade of progressive experience in early and late-stage health technology companies, most recently serving as Associate Vice President of Customer Success at Unite Us, where she led customer success teams supporting coordinated care networks across the country.
The hire reflects Upside’s continued investment in client experience as the company deepens partnerships with health plans and employers tackling housing instability across Medicaid, Medicare Advantage, D-SNP, and commercial populations. As SVP of Client Success, Alex will oversee the full lifecycle of Upside’s health plan and employer relationships — from implementation through performance reporting — ensuring that partner organizations see measurable impact from the program.
“Alex has spent her career building the kind of client partnerships that endure, regardless of the economic climate,” said Chuck Hector, Chief Revenue Officer of Upside. “What we do is complicated. We’re placing high-acuity members in housing, navigating landlords, moving people across Medicaid systems — and our health plan partners need someone who can translate that complexity into confidence. Alex has done this at Unite Us, at Carrot Health, for years. She knows that client success in health tech isn’t about renewals — it’s about outcomes. That’s exactly what we need as we grow.”
Prior to Unite Us, Alex spent three and a half years at Carrot Health, a Minneapolis-based health data and analytics company, where she held roles in both customer growth and customer success leadership. Earlier in her career, she led client services and implementation at Benovate, a health and wellness platform, where she built and managed client relationships from pre-contract through ongoing program management. Alex is based in Minneapolis, Minnesota.
“Housing instability sits at the intersection of health outcomes, care costs, and human dignity — and Upside has built a model that treats all three seriously,” said Alexandra Earl, Senior Vice President of Client Success of Upside. “I’ve spent my career at mission-driven companies in health tech, and I know what it takes to turn a good program into one that health plans and employers trust for the long run. What drew me to Upside is the care built into every part of the model — from the Care Guides working directly with members to the data that helps partners understand what’s actually changing. I’m here to make sure every client feels that, and sees it in their results.”
Upside’s model pairs dedicated Care Guides — licensed social workers and housing specialists — with AI-supported housing orchestration to identify and stabilize members facing housing instability before a crisis drives avoidable emergency care. The company serves health plans and employers across the full housing continuum, from crisis intervention to long-term tenancy support.
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.
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Upside Corporate Headquarters
200 E Las Olas Blvd 14th Floor
Fort Lauderdale, FL 33301
