Upside Names Patrick Regan Executive Vice President of Sales and Go-to-Market

The enterprise sales leader joins Upside to build the go-to-market team behind a category most health plans are still learning how to buy.

FORT LAUDERDALE, FL — Upside, a nationally scalable housing stability platform purpose-built for healthcare, today announced that Patrick Regan has joined the company as Executive Vice President of Sales and Go-to-Market. Regan brings nearly a decade of enterprise sales leadership, with a record of building teams, processes, and training programs that produce consistent results. He will lead sales and go-to-market strategy as Upside expands its work with health plans and employers.

Regan joins at a point when housing is moving from a talking point to a line item for health plans. Most plans now accept that unstable housing drives cost and worsens outcomes. Fewer have a way to act on it. That makes the sales conversation part education and part proof, and it requires a team that can carry a long, complex buying process without overselling what happens after the contract is signed. Regan will build that team.

“We needed someone who could sell something the market has not finished defining yet,” said Jake Rothstein, Co-Founder and Chief Executive Officer of Upside. “That takes conviction and patience, not just a pipeline. Patrick has both. He is also the kind of leader people follow, and at this stage of a company that matters as much as the number.”

Before joining Upside, Regan spent nearly five years at MotionPoint, rising from enterprise account executive to Vice President of Sales for the enterprise localization technology company. Earlier, he spent more than three years at Meltwater in roles spanning sales executive, sales manager, and key account executive. Across both companies he built and led teams selling complex technology into large organizations with long decision cycles. Regan holds a bachelor of science in entrepreneurship and small business management from the Florida State University Herbert Wertheim College of Business.

“Sales and delivery are the same job here,” said Peter Badgley, Co-Founder and Chief Operating Officer of Upside. “Whatever we promise a plan in a room, our Care Guides have to make real in the field, often for someone in crisis. Patrick understands that difference and he is building a team that respects it.”

“In managed care we have gotten comfortable calling a referral a closed loop. It is not,” said Patrick Regan, Executive Vice President of Sales and Go-to-Market of Upside. “The loop closes when a member has a key in hand and somewhere safe to sleep. I joined Upside because the model is built to get to that point and to prove it happened. My job is to build a team that sells that honestly, then goes and earns it.”

Regan’s appointment reflects Upside’s continued investment in the go-to-market work behind its growth. 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.