Associate Director of Customer Success (Remote)

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.

About the Opportunity:

Upside is hiring an Associate Director of Health Plan Success to manage, retain, and grow relationships with key health plan customers. This is a senior individual contributor role with day-to-day ownership of a complex portfolio of health plan customers, which may include large national payer organizations, affiliated health plans, and other strategic accounts. 

The Associate Director will serve as a trusted partner to customer stakeholders, helping ensure strong program performance, customer satisfaction, and long-term retention. This person will also identify opportunities to increase referrals, expand into new populations or lines of business, and extend or renew existing contracts.

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

Work Location and Schedule:

• 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. 

What You’ll Do:

• Own day-to-day relationships for an assigned portfolio of health plan 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

• Identify and address customer risks before they impact retention

• Own renewal planning and execution for assigned accounts

• Identify 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, renewal timelines, risks, and expansion opportunities in Salesforce

• Help build Customer Success processes, playbooks, reporting, and OKRs as the team scales

What We’re Looking For:

• 6+ years of experience in customer success, account management, partnerships, or client services

• Experience working with health plans, managed care organizations, or other complex healthcare customers

• Strong understanding of Medicaid, Medicare Advantage, D-SNP, case management, or social drivers of health

• Proven success managing, retaining, and growing high-value customer relationships

• Experience with renewals, cross-selling, referral growth, or account expansion

• Strong presentation, communication, and relationship-building skills

• Ability to operate independently and manage multiple complex accounts without significant oversight

• Experience working cross-functionally in a startup, SaaS, or technology-enabled services environment

• Proficiency with Salesforce or a similar CRM

• Ability to work effectively across multiple time zones

Compensation and Benefits:

• Base salary: $115,000–$130,000

• Performance-based variable compensation

• Medical, dental, and vision coverage

• Paid time off and company holidays

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.