VP, Customer Success & Retention

HealthJoy•Tampa, FL

4h•Remote

About The Position

HealthJoy is a growing global company with over 300 team members, focused on making healthcare benefits simple, connected, and valuable. We are seeking a VP, Customer Success & Retention to protect and grow our revenue base by leading a transformation in how our Customer Success organization operates in an AI-native company. This role is crucial for defending revenue, driving expansion, and building an agentic Customer Success motion that allows for efficient management of growing business. The ideal candidate will be excited about leading an organization that leverages AI and agents to handle heavy lifting, reinventing CS workflows, and driving outcomes through data and strategic relationships.

Requirements

8+ years in Customer Success, account management, or a commercial retention role, including team leadership.
Proven experience owning a retention or net revenue retention number and leading the people responsible for delivering it.
Experience defending and growing a B2B book of business.
Revenue-first mindset, connecting every CS activity to a business outcome and holding self and team accountable to the number.
Genuine excitement to lead a Customer Success organization where AI and agents do the heavy lifting, and comfort building and iterating on workflows.
Commercial and cross-functional fluency, operating comfortably with Sales, Marketing, RevOps, Data, Product, and Legal.
Understanding of how broker-channel dynamics shape retention in benefits.
Comfort with data and systems, living in Salesforce, pulling own metrics, spotting signal in noise, and making team reporting a source of truth.
Comfort with ambiguity, building things from scratch, changing how work is done, and shaping the role.
Executive presence and clarity, communicating well at all levels and able to run QBRs, lead business reviews, defend renewals, and write clear, persuasive emails.

Nice To Haves

Hands-on experience designing AI-augmented or agentic processes.
Healthcare or benefits experience.

Responsibilities

Own net revenue retention and gross retention, including the renewal calendar, churn-risk triage, and forecasting discipline.
Drive expansion and product adoption by owning the upsell pipeline and product-adoption motion to activate clients and prove ROI.
Lead the AI-native transformation of Customer Success by owning and advancing the agentic customer lifecycle roadmap.
Run the Customer Success team out of Salesforce, ensuring it serves as the system of record for forecasting, opportunity management, and book health.
Own the broker-advocacy dimension of retention by partnering with the broker partnership team and Sales to equip brokers with renewal narratives and ROI proof.
Act as the senior voice for clients, participating in QBRs, business reviews, escalations, and managing the Customer Advisory Board and Voice of Customer program.
Lead and develop the Customer Success team, raising the commercial sophistication of the organization and ensuring team members focus on judgment rather than busywork.
Bring data to the table by knowing retention, expansion, and engagement metrics, spotting trends, and turning them into action.