VP, Customer Success & Retention

About HealthJoy

HealthJoy simplifies complex healthcare benefits, making them accessible and valuable for employees. The company focuses on creating connected, understandable benefit experiences that drive employee engagement and organizational value. Recognized for its innovation and growth, HealthJoy is a remote-first employer committed to transforming the healthtech landscape. The company is actively reinventing its Customer Success function with an AI-native strategy to maintain its competitive edge.

The Role

This commercial leadership role centers on owning Customer Success and the critical Net Revenue Retention (NRR) number. You will be responsible for protecting and expanding revenue across the employer client base while leading the team through a significant operational transformation powered by AI. This position demands a revenue-first mindset, with outcomes like NRR, gross retention, and expansion being paramount. You will manage the renewal calendar, triage churn risk, drive upsell and product adoption, and ensure the health of client relationships from inception through renewal, utilizing Salesforce as your primary management tool.

What You'll Do

• Own Retention Metrics: Take full ownership of Net Revenue Retention (NRR) and Gross Retention. Manage the renewal calendar, identify at-risk accounts, and implement rigorous forecasting for churn prediction.
• Drive Expansion and Adoption: Lead the upsell pipeline and product adoption initiatives, ensuring clients activate products that enhance stickiness and demonstrate ROI. Set targets, track progress, and hold the team accountable for outcomes.
• Lead AI-Native Transformation: Advance the agentic customer lifecycle roadmap, developing and deploying AI agents for business reviews, renewal proposals, upsell discovery, automated outreach, and predictive health scoring. Partner with Data, Product, and RevOps to ensure data integrity and leverage AI as a multiplier for team judgment.
• Manage Out of Salesforce: Utilize Salesforce as the system of record for forecasting renewals, managing opportunities, and tracking book health, ensuring a single source of truth for the team's operations.
• Own Broker Advocacy: Collaborate with the broker partnership team and Sales to address churn risk concentrated in accounts with low broker engagement. Equip brokers with renewal narratives and ROI proof, and engage directly with clients when necessary.
• Serve as Senior Client Voice: Represent the company in key client interactions, including QBRs, business reviews, escalations, and incident communications. Lead the Customer Advisory Board and Voice of Customer program, channeling feedback into product and marketing strategies.
• Lead and Develop the Team: Manage a team of CS managers and CSMs, enhancing their commercial sophistication and building a strong talent pipeline. Ensure the team focuses on strategic judgment rather than routine tasks as the workload evolves.
• Deliver Data-Driven Insights: Maintain a deep understanding of retention, expansion, and engagement metrics, identify trends, and translate them into actionable strategies without relying solely on external data support.

What We're Looking For

• Experience: 8+ years in Customer Success, account management, or a commercial retention role, including team leadership. Proven track record of owning and delivering retention/NRR numbers for B2B accounts.
• Revenue-First Mindset: A focus on retention, expansion, and NRR, connecting all CS activities to business outcomes and holding oneself and the team accountable to targets.
• AI-Native Enthusiasm: Genuine excitement for leading an AI-powered Customer Success organization. Comfort with building and iterating on AI-augmented or agentic workflows is crucial; hands-on experience is a strong plus. A builder's curiosity is non-negotiable.
• Commercial Fluency: Ability to operate effectively across Sales, Marketing, RevOps, Data, Product, and Legal. Understanding of broker-channel dynamics in benefits and experience driving outcomes through cross-functional relationships.
• Data & Systems Proficiency: Strong command of Salesforce, ability to pull and analyze metrics, identify trends, and establish reporting as a source of truth.
• Comfort with Ambiguity: Ability to thrive in a transformative function, build from scratch, and shape the role and processes as they evolve.
• Executive Presence: Clear and effective communication skills across all levels, from individual contributors to C-suite executives and clients.
• Preferred Experience: Healthcare or benefits industry experience is preferred but not required; strong commercial CS leadership and domain curiosity are key.

This Role Is Not for Everyone

This role is for individuals seeking a transformative challenge in an AI-driven environment, not for those preferring a steady-state, playbook-driven approach. If AI feels like a threat rather than an opportunity, or if certainty is required before action, this role may not be the right fit. Success requires a proactive, builder's mindset and comfort with ambiguity.

Reporting & Team

This role reports to the Chief Growth Officer and leads the Customer Success organization. You will collaborate closely with Sales, Broker Partnerships, Marketing, RevOps, Data, Product, and Legal, with significant visibility into senior leadership.

Total Rewards

• Compensation: This role includes a base salary and commissions. To request overall compensation details, please email hr@healthjoy.com.
• Health & Wellness: Medical, Dental, and Vision insurance packages; HSA contribution match; Company-sponsored Short Term and Long Term Disability coverage.
• Retirement: 401k match.
• Equity: Stock options for eligible roles.
• Time Off: Flexible PTO.
• Family Support: Paid parental leave.
• Location Preference: While HealthJoy is remote-first, this role has a preference for candidates in the Tampa Bay area.

Commitment to Equal Pay & Opportunity

HealthJoy is committed to diversity, inclusion, and equal pay. Compensation is based on qualifications and experience, ensuring fairness. The company is an equal opportunity employer, encouraging all qualified applicants to apply, even if they don't meet every single requirement.