The Senior Director of Health Plan Client Success is a high-impact, client-facing leadership role responsible for managing and growing relationships with Upside’s key health plan clients. This role serves as the primary strategic partner for an assigned portfolio of accounts, ensuring client satisfaction, retention, and growth through hands-on engagement and operational excellence.

Reporting to the VP of Health Plan Client Success, the Senior Director will begin as an individual contributor owning high-value client accounts, then scale into a people-leadership role as the team grows. This position requires someone who can build deep, trust-based relationships with client stakeholders while driving measurable outcomes and identifying expansion opportunities. The ideal candidate combines healthcare industry expertise with strong operational rigor and a client-first mindset.

Responsibilities

• Serve as the primary strategic partner for assigned health plan client accounts, ensuring satisfaction and long-term retention
• Establish and maintain deep, trust-based relationships with senior client stakeholders to align Upside solutions with their goals
• Conduct regular check-ins, lead quarterly business reviews, and deliver performance updates on client programs
• Collaborate with sales, product, and implementation teams to ensure seamless onboarding, delivery, and client goal achievement
• Identify and pursue expansion opportunities within assigned accounts, including new programs, geographies, and populations
• Develop and refine client success playbooks, processes, and best practices in partnership with the VP
• Mentor and coach team members as the client success organization scales
• Monitor client health metrics and proactively address risks before they impact satisfaction or retention
• Stay current on healthcare industry trends to ensure client strategies remain relevant and forward-looking

Requirements

• Bachelor’s or Master’s degree in Business Administration, Public Health, Healthcare Administration, or a related field
• 5+ years of proven success in client success, account management, or relationship management with a healthcare or health plan focus
• Strong understanding of the healthcare payer industry, including regulatory environments, reimbursement policies, and emerging market trends
• Track record of achieving and exceeding client satisfaction, retention, and growth goals
• Exceptional communication, presentation, and relationship-building skills
• Demonstrated ability to work independently, manage multiple priorities, and thrive in a fast-paced environment
• Proficiency with CRM and enablement tools (Salesforce, HubSpot preferred)
• Willingness to travel as needed for client engagement and relationship development

Preferred Qualifications

• Experience working directly with Medicaid, Medicare Advantage, or D-SNP health plans
• Background in social determinants of health, housing services, or community-based care models
• Experience mentoring or managing client-facing team members

Compensation & Benefits

• Market competitive base salary with performance-based incentives and stock options
• Comprehensive benefits package including medical, dental, and vision coverage
• PTO and paid holidays
• Professional development and career growth opportunities

About Upside

Upside is redefining healthcare by connecting housing stability to better health outcomes. Through our integrated platform, we partner with health plans and payers to identify members at risk of housing instability, develop individualized housing plans, secure placements, and track outcomes over time. By addressing housing as a core social determinant of health, Upside helps reduce avoidable utilization, improve member stability, and deliver measurable ROI. Headquartered in Ft. Lauderdale, Florida, with 32,000+ nationwide communities and properties in our network, Upside is the first and only housing-dedicated service combining human interaction, AI, and a managed real estate network for rapid outcomes and satisfaction.

Equal Opportunity Statement

Upside is an Equal Opportunity Employer and is committed to providing a drug-free workplace. We do not discriminate against any employee or applicant for employment because of race, color, sex, age, national origin, religion, sexual orientation, gender identity, status as a veteran, disability, or any other protected class. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions of this role.