Upside Names Christopher Gambino Senior Director of Business Operations

The digital health operator, who has helped scale healthcare platforms from early stage through national expansion, joins Upside to build the operating model behind its growth.

FORT LAUDERDALE, FL — Upside, a nationally scalable housing stability platform purpose-built for healthcare, today announced that Christopher Gambino has joined the company as Senior Director of Business Operations. Gambino brings a track record of helping high-growth healthcare and wellness organizations scale from early stage through national expansion, with deep experience operationalizing growth for digital health platforms. He will build and lead the operating model behind Upside’s growth, aligning people, process, and technology across the business.

Gambino joins as Upside scales its work with health plans and employers addressing housing instability across Medicaid, Medicare Advantage, and D-SNP populations. As the company grows, disciplined operations are what turn strategy into measurable results in the field. Gambino’s experience across digital health, value-based care, Medicare, Medicaid, and employer health positions him to build the operating backbone that lets Upside’s Care Guides deliver at scale.

“Chris knows how to turn strategy into execution, which is exactly what a growing operation needs,” said Austin Burch, Senior Vice President of Operations of Upside. “Our Care Guides do hard, human work in the field every day. Chris is building the operating model that lets them do more of it, without losing what makes it work.”

Before joining Upside, Gambino founded an advisory practice helping founders translate strategy into execution across digital health. Earlier, he served as Head of RevOps and Strategy at Tivity Health, Head of Client Operations and Strategy at Papa, a digital health company partnering with Medicare and Medicaid payers, and VP of Operations and Chief of Staff at Peerfit.

“I have spent my career operationalizing growth for healthcare platforms, and Upside is building something genuinely new at the intersection of healthcare and housing,” said Christopher Gambino, Senior Director of Business Operations of Upside. “Housing is one of the most complex drivers of health, and this is a model built to produce real, measurable outcomes. My job is to align the people, process, and technology behind it so that impact scales.”

Gambino’s appointment reflects Upside’s continued investment in the operational discipline 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 depth to meet them — helping members solve housing problems to completion so the lease gets signed and the ER visits stop.