Senior Director, Customer Success

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 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.

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 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

What We’re Looking For:

• 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 oversight

• Demonstrated executive presence: confident, polished, and credible in front of C-suite and senior health plan leadership

• Proven success managing, retaining, and growing high-value customer relationships, including complex renewals and expansions

• Experience driving renewals, cross-selling, referral growth, or account expansion at a strategic level

• Experience leading, mentoring, or managing teams is a plus, with the potential for this role to evolve into a people leadership position as the team scales.

• Exceptional presentation, communication, and relationship-building skills, with the gravitas to lead high-stakes conversations

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

• Ability to creatively problem solve, and consistently apply critical thinking 

• Proficiency with Salesforce or a similar CRM

• Ability to work effectively across multiple time zones

Compensation and Benefits:

• Base salary: $150,000-$175,000

• 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.