Associate Director, Customer Success

About Upside

Upside is a dedicated housing-focused care partner committed to assisting individuals facing housing instability in achieving stable living situations. We collaborate with health plans and care organizations to identify at-risk members, develop actionable housing plans, and oversee entire processes from placement to stabilization. The team manages all aspects, including member engagement, local provider and community resource coordination, logistics, documentation, and ongoing support until resolution is achieved. Our approach emphasizes humanity and measurable outcomes such as stable housing, successful moves, safer environments, and smooth transitions.

Role Overview

The Associate Director of Health Plan Success is responsible for managing, nurturing, and expanding relationships with key health plan clients. This senior individual contributor role encompasses ownership of a complex portfolio that may include large national payers, affiliated plans, and strategic accounts. Reporting directly to the SVP of Customer Success, this role acts as a trusted advisor to customer stakeholders, driving program performance, satisfaction, and retention, while identifying growth opportunities like increased referrals, new population segments, or contract renewals and extensions.

Work Location and Schedule

• Full-time position, fully remote across the United States
• Ability to effectively collaborate across multiple U.S. time zones
• Willingness and availability to travel for customer meetings, business reviews, and meaningful relationship development

Key Responsibilities

• Manage daily relationships for an assigned set of health plan accounts
• Serve as the main contact for customer stakeholders
• Lead regular customer meetings, quarterly business reviews, and provide program performance updates
• Track account health, satisfaction levels, referral volumes, and overall program effectiveness
• Proactively detect and mitigate risks that could jeopardize customer retention
• Oversee planning and execution of contract renewals
• Spot opportunities to grow referrals, broaden service lines, and extend contracts
• Collaborate cross-functionally with Sales, Operations, Product, and leadership to align with customer objectives and drive growth
• Maintain detailed account plans, renewal schedules, risk assessments, and expansion prospects using Salesforce
• Contribute to the development of Customer Success playbooks, reporting frameworks, and performance objectives as the team expands

Candidate Profile

• At least six years of experience in customer success, account management, partnerships, or client services
• Familiarity with health plans, managed care organizations, or complex healthcare customer environments
• Solid understanding of Medicaid, Medicare Advantage, D-SNP, case management, or social determinants of health
• Proven track record in managing, retaining, and growing valuable customer relationships
• Demonstrated experience with contract renewals, upselling, referral growth, or account expansions
• Excellent communication, presentation, and relationship-building skills
• Self-driven with the capability to independently manage multiple complex accounts
• Experience operating in startup, SaaS, or technology-enabled services settings
• Proficiency with Salesforce or comparable CRM tools
• Ability to work seamlessly across various time zones

Compensation and Benefits

• Base salary range of $115,000 to $130,000
• Performance-based variable compensation
• Medical, dental, and vision insurance coverage
• Paid vacation and company-observed holidays

Equal Opportunity and Accommodations

Upside embraces equal employment opportunity without discrimination based on race, religion, color, national origin, age, gender, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, pregnancy, or other legally protected characteristics. The company is committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans. Applicants needing accommodations should communicate their requirements.