Head of Client Success – Wellbeing

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead and cultivate a global organization of managers and their teams serving around 1,000 large direct employer, channel, and health plan clients.

• Drive transformative change by establishing the Customer Success vision and realigning team structures and operational methods.

• Take ownership of client satisfaction, annual renewals, retention, and net growth objectives.

• Manage client health scoring and retention forecasting.

• Implement “Land and Expand” strategies through cross-selling, upselling, and encouraging the adoption of product expansions.

• Report on client outcomes and ROI while converting successful clients into references.

• Serve as a strategic advisor and executive sponsor to senior client decision-makers.

• Participate in selected quarterly and annual client reviews.

• Establish standards for strategic recommendations and action plans aligned with client objectives.

• Oversee the Customer Success P&L, including workforce planning, forecasting, and cost-to-serve management.

• Utilize automation and AI where beneficial.

• Share the product roadmap with clients and advocate for the client voice at the executive level.

• Collaborate with internal leaders to address client needs and enhance the offering.

• Represent Customer Success in mid- and late-stage strategic sales efforts.

• Work alongside fellow executives to dismantle silos and promote continuous improvement.

• Monitor the health technology landscape and shape strategy and execution.

• Report directly to the Chief Growth Officer, Wellbeing.

• Act as a member of the Personify Wellbeing Commercial Leadership Team and contribute to strategic and cross-functional planning.

⛳️ Requirements

• Bachelor’s degree required; MBA preferred.

• 10+ years of experience in progressively senior leadership roles in customer success, account management, or professional services.

• Proven experience in leading managers and large teams.

• Preferred domain experience in digital health, wellbeing, total rewards, health plans, or benefits administration.

• Demonstrated success in a consultative account executive environment.

• Experience in cultivating relationships with senior client decision-makers.

• Experience in leading a global organization within a complex, matrixed, cross-functional setting.

• P&L accountability.

• Proven track record of driving transformative change.

• Experience in leading a Customer Success function with a commercial focus.

• Strong emphasis on strategic client advising and promoting the adoption of product expansions.

• History of building leadership teams that achieve profitable results.

• Experience in analyzing client health metrics and proactively identifying retention risks.

• Experience in realigning team structures for optimized success.

• Possess executive presence, emotional intelligence, innovative spirit, and a data-driven approach.

• Excellent communication skills, including the ability to brief executives and boards as well as public speaking.

• Passionate about client success, health, and wellbeing.

• Willingness to travel 25–50% of the time.

• Ability to consistently operate a computer and other productivity equipment.

• Effective communication of information and ideas clearly and accurately.

• Ability to observe details at close range.

🏝️ Benefits

• Competitive base salary and benefits effective from day one.

• Comprehensive medical and dental coverage through our own health solutions.

• Unlimited PTO.

• Mental health support.

• Retirement planning.

• Financial protection.

• Opportunities for professional development with clear career progression and learning budgets.

• Mission-driven culture where diverse perspectives create real impact.

• Wellness programs.

• Additional employee perks.