Upside Names Brad Cillan General Manager of Employer Solutions

The housing stability company adds a veteran employee benefits leader to accelerate growth in the employer market as housing instability becomes an increasingly visible workforce issue.

FORT LAUDERDALE, FL — Upside, the 1st housing stability employee benefit, announced today the appointment of Brad Cillian as General Manager of Employer Solutions. Cillian joins Upside from GRAIL, where he led US employer distribution partnerships across brokers, consultants, captives, and stop loss carriers. In this new role, he will lead Upside’s employer line of business — building and managing relationships with self-insured employers, multi-employers, unions, brokers, and benefit consultants who are looking to address housing instability as a driver of workforce performance and healthcare cost.

Housing stability as a corporate strategy is helping employers reduce medical costs, improve engagement and improve productivity.  Over the last 6 years Upside has been growing very quickly while partnering with over 20 health plans to provide housing stability services for members and is now available for employers, multi-employers and unions. 

Upside’s employer program connects employees with housing stability events to dedicated Care Guides — licensed social workers and housing specialists — who work alongside employees to resolve housing problems and restore stability. The result is a workforce benefit that produces measurable returns in retention, productivity, and healthcare cost reductions.

“Brad is exactly the kind of operator we need to grow the employer side of this business,” said Chuck Hector, Chief Revenue Officer at Upside. “He’s spent his career in total rewards and building distribution channels — at Lockton, at IMA, at GRAIL — and he knows how self-insured employers actually think and buy. Housing instability hits even your $75,000-to-$100,000-a-year employees. A surgery, a job loss in the family, a few missed paychecks — and someone who was performing is suddenly in a spiral. Brad gets that. He also understands that benefit consultants and innovative distribution partners are where this conversation starts.”

Cillian brings more than two decades of experience across employee benefits, human capital consulting, and employer distribution partnerships. His career spans senior leadership roles at Lockton Companies, IMA Financial Group, Mercer, and GRAIL, where he worked directly with self-insured employers, brokers, and human capital consulting firms to build and scale innovative consulting and total rewards solutions. 

He holds a Bachelor of Science in Marketing from Miami University’s Farmer School of Business, and has completed executive programs at UC Berkeley and the Disney Institute.  

“Housing stability is becoming a corporate strategy and is now an employee benefit” said Brad Cillian, GM of Employer Solutions at Upside. “Housing stability can be tied to medical claims reductions including reduced ER utilization, lower mental health claims, drops in comorbidity exacerbations and workers compensation cost reductions. Productivity and performance gains are experienced and we see turnover reduction and increased work engagement when housing stability is part of a total rewards strategy” 

Cillian’s appointment reflects Upside’s continued investment in the employer market as the company expands its reach across Medicaid, Medicare Advantage, and employers. With a distribution model built for brokers, consultants and innovative partners, Upside is positioned to bring its Care Guide model to employers, multi-employers and unions across the country.

About Upside

Upside is a nationally scalable housing stability platform purpose-built for healthcare and employers. 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. For more information, visit www.joinupside.com.

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