The Vice President of Health Plan Client Success is an executive leadership role responsible for defining and executing the overall client success strategy for Upside’s health plan partnerships. This leader will own the full lifecycle of client relationships at the most senior level, from strategic onboarding through long-term expansion, and will be accountable for retention, growth, and satisfaction across the health plan portfolio.

Reporting directly to the CRO, this role sets the vision for how Upside engages, retains, and grows its health plan client base. The VP will build and lead a high-performing client success organization, establish scalable processes and playbooks, and serve as the executive sponsor for Upside’s most strategic client relationships. This is a hands-on leadership role that requires equal parts strategic thinking and client-facing execution.

Responsibilities

• Define and own the client success strategy for Upside’s health plan portfolio, setting goals for retention, expansion, and satisfaction
• Serve as the executive sponsor and escalation point for Upside’s largest and most strategic health plan clients
• Build, lead, and scale the client success organization, including hiring, mentoring, and performance management
• Establish client success frameworks, playbooks, KPIs, and reporting infrastructure to drive accountability and consistency
• Lead executive-level quarterly business reviews and strategic planning sessions with client stakeholders
• Partner with the CRO, sales, product, and operations leaders to align client needs with company strategy and product roadmap
• Identify and drive expansion opportunities across existing accounts, including new programs, geographies, and populations
• Represent the voice of the client internally, influencing product development, service design, and go-to-market strategy
• Stay current on healthcare industry trends, regulatory changes, and competitive dynamics to keep Upside ahead of market shifts

Requirements

• Bachelor’s or Master’s degree in Business Administration, Public Health, Healthcare Administration, or a related field
• 8+ years of progressive experience in client success, account management, or strategic partnerships, with at least 3 years in a senior leadership role
• Deep expertise in the healthcare payer landscape, including regulatory environments, value-based care models, and population health strategies
• Proven track record of building and scaling client success teams from the ground up
• Executive-level communication, presentation, and relationship-building skills
• Demonstrated ability to manage a portfolio with significant revenue responsibility and deliver measurable client outcomes
• 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 leading client success through periods of rapid organizational growth or transformation

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.