Senior Director, Customer Success

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.

Upside is hiring a Senior Director of Customer Success to lead our most strategic customer relationships. This is a senior leadership role with expanded ownership across a portfolio of high-value partnerships – including large national and regional health plans – where the complexity, stakes, and seniority of stakeholder relationships are the highest in our book of business. While the role initially focuses on payer customers, it may evolve to include responsibility for high-value employer group partnerships.

The Senior Director will be Upside’s most senior day-to-day relationship owner for these accounts, trusted to represent Upside credibly and confidently in front of C-suite and senior customer leadership. Beyond strong account management fundamentals, this person brings the executive presence and polish to build trust quickly at the highest levels, lead strategic conversations, and protect and grow some of our most important partnerships.

This role reports to the SVP of Customer Success. Internally, this role is referred to as Senior Director, Customer Success.

• Full-time, fully remote within the United States
• Must be able to work effectively across multiple U.S. time zones
• Must be available to travel as needed for customer meetings, business reviews, and other key relationship-building activities

• Own day-to-day and strategic executive relationships for an assigned portfolio of customers
• Serve as the primary point of contact for customer stakeholders
• Lead recurring customer meetings, quarterly business reviews, and performance updates
• Monitor account health, customer satisfaction, referral volume, and program performance
• Proactively identify and address customer risks before they impact retention
• Own retention and growth strategy for assigned accounts, aligning Upside goals with customer objectives
• Identify and work opportunities to increase referrals, expand into new populations or lines of business, and extend existing contracts
• Partner with Sales, Operations, Product, and leadership to support customer goals and growth
• Maintain clear account plans, contacts, renewal and expansion opportunity forecasts, and risks in Salesforce
• Help build Customer Success processes, playbooks, reporting, and OKRs as the team scales
• Champion Voice of the Customer; continuously elevate customer and market feedback

• 9+ years of experience in customer success, account management, partnerships, or client services, with a track record of owning and growing the most strategic, highest-value relationships in your portfolio
• Senior-level experience working with health plans, managed care organizations, or other complex healthcare customers. Experience with large employer groups is a plus.
• Strong understanding of Medicaid, Medicare Advantage, and D-SNP. Additional experience with case management, or social drivers of health is a plus.
• Deep, proven account management expertise – able to navigate complex, multi-stakeholder accounts with sound judgment and minimal…