Available Positions

Senior Director of Health Plan Client Success

Job Description

As the Senior Director of Health Plan Client Success, you will be responsible for cultivating and expanding relationships with Upside’s key health plan clients. Acting as a trusted advisor, you will ensure client satisfaction, retention, and growth by driving strategic alignment and outcomes. Your role will begin as an individual contributor, taking ownership of high-value client accounts and engaging directly with stakeholders to meet their evolving needs. Over time, this position will expand into a leadership role, scaling and managing a high-performing client success team.

You will work closely with product, sales, and implementation teams to ensure seamless client delivery, lead quarterly business reviews, and identify new opportunities within existing accounts. This is a dynamic, client-facing position that requires exceptional communication skills, deep healthcare knowledge, and the ability to translate client needs into actionable outcomes.

Qualifications

• Bachelor’s or Master’s degree in Business Administration, Public Health, Healthcare Administration, or related field preferred
• 5+ years of proven success in client success, account management, or relationship management (healthcare or health plan focus strongly preferred)
• Strong understanding of the healthcare industry, including regulatory environments, reimbursement policies, and emerging market trends
• Track record of achieving and exceeding client satisfaction, retention, and growth goals
• Exceptional communication, presentation, and relationship-building skills
• Demonstrated ability to work independently, manage multiple priorities, and thrive in a fast-paced environment
• Proficiency with CRM and enablement tools (Salesforce, HubSpot preferred)
• Willingness to travel as needed for client engagement and relationship development

Duties and Essential Functions

• Serve as the strategic partner for key health plan clients, ensuring satisfaction and long-term retention
• Establish and maintain deep relationships with senior stakeholders to align Upside solutions with client needs
• Conduct regular check-ins, lead quarterly business reviews, and deliver performance updates on client programs
• Collaborate with sales, product, and implementation teams to ensure seamless onboarding, delivery, and client goal achievement
• Identify and drive expansion opportunities within existing accounts, including whitespace growth and cross-vertical opportunities
• Develop client success strategies, playbooks, and best practices to strengthen client relationships
• Train, mentor, and eventually lead a client success team as the role scales
• Stay current on healthcare industry trends to ensure Upside remains at the forefront of client success innovation

Compensation and Benefits

• Market competitive base salary with performance-based incentives and stock options
• Comprehensive benefits package, including medical, dental, and vision coverage
• PTO + paid holidays
• Professional development and career growth opportunities

Company Summary

Upside is redefining access to affordable living by helping older adults, vulnerable persons and employees of corporations traverse the housing landscape efficiently through a curated experience managed by a personalized housing care guide. Headquartered in Ft. Lauderdale, Florida but boasting 32,000+ nationwide communities and properties in our available network, Upside is the first and only housing dedicated service combining human interaction + AI + a managed real estate network for rapid outcomes and satisfaction.

Equal Opportunity Statement

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions of this role. Upside is an Equal Opportunity/Affirmative Action 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.