Flex Funds Support Specialist

About Upside: Upside is a housing-focused care partner helping people experiencing housing instability take the next step toward stability. We partner with health plans and care organizations to identify members at risk, build a clear housing plan, and drive the work forward through placement and stabilization. Upside owns the entire housing process from start to finish. Our team engages members, coordinates with local providers and community resources, manages logistics and documentation, and stays involved until the issue is resolved. Our approach is human-first and outcome-driven, measured by real results like stable housing, completed moves, safer living environments, and successful transitions. Our Values: At Upside, our values shape how we work, how we make decisions, and how we show up for our members, partners, and each other. Compassion: Lead with empathy, meet people where they are, and approach our work with care. Ambition: Think bigger than today, move with urgency, and challenge ourselves to solve hard problems. Respect: Communicate openly, act with integrity, and assume positive intent. Excellence: Good enough isn’t good enough. Take ownership and deliver outcomes that exceed expectations. About the Opportunity: The Flex Funds Support Specialist will own the day-to-day execution of Flex Funds requests that help members successfully move into and maintain stable housing. This includes reviewing documentation, managing submissions and approvals, tracking payments, and coordinating closely with Care Guides, members, landlords, vendors, health plans, and internal teams. This person will become a subject matter expert on Flex Funds requirements across different states and health plans, helping ensure requests are accurate, complete, and compliant with plan-specific rules. This is a highly operational role for someone who is organized, solution-oriented, and comfortable balancing high-volume execution with process improvement and internal guidance. Work Location and Schedule: Full-time, remote within the United States Open to candidates in Eastern and Western time zones Standard business hours with flexibility to support members, partners, and internal teams across time zones What You’ll Do: Own Flex Funds requests from intake through approval, payment, and completion, including housing deposits, furniture, application fees, and other eligible housing-related needs Assist in collecting and reviewing documentation and ensure requests are complete, accurate, and meet health plan-specific requirements before submission Develop deep expertise in Flex Funds requirements across different states and health plans, including eligibility, required documentation, allowable expenses, and approval processes Prepare and submit complete requests to health plans and manage ongoing communication related to approvals, denials, missing information, and next steps Coordinate closely with Care Guides, members, landlords, property managers, vendors, Finance, and health plan partners to keep requests moving and resolve blockers quickly Track requests, approvals, payments, deadlines, and supporting documentation across internal systems, ensuring records are accurate and audit-ready Support the distribution and tracking of funds in cases where Upside administers payments directly Build and maintain strong partnerships and relationships with Health Plan counterparts to ensure trust, quality, and efficiency Serve as a resource to Care Guides and internal teams, providing clear guidance on what is and is not allowable under each plan’s Flex Funds program Identify recurring issues, gaps, and opportunities to improve workflows, training, documentation, and overall program efficiency What We’re Looking For: 2–4 years of experience in operations, care coordination, case management, healthcare administration, housing services, financial assistance, benefits administration, or a similar role Experience managing documentation-heavy, multi-step workflows with multiple stakeholders Exceptional organization and attention to detail, with the ability to manage a high volume of active requests without losing track of deadlines or requirements Strong written and verbal communication skills and comfort coordinating across members, landlords, external partners, health plans, and internal teams A solution-oriented mindset and willingness to proactively surface problems, investigate blockers, and drive issues toward resolution Strong judgment and confidence applying established rules consistently, including the ability to communicate when a request cannot be approved and clearly explain why Ability to learn and retain different requirements across health plans, states, and programs and become a trusted subject matter expert Comfort working in a fast-paced, highly transactional environment where speed and accuracy are equally important Experience with Salesforce or another case management / CRM system preferred Experience within healthcare, Medicaid, housing services, social services, or another regulated environment preferred Compensation and Benefits: $25-$28/hour Medical, dental, and vision coverage Paid time off and company holidays Additional benefits in accordance with Upside’s current benefits offerings Upside is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, pregnancy, or other applicable legally protected characteristic. Upside is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans. If you have a disability or special need that requires accommodation, please let us know.