VP, Customer Success & Retention

HealthJoy•Tampa, FL

3d•Remote

About The Position

HealthJoy is seeking a VP, Customer Success & Retention to lead their Customer Success organization. This role is focused on protecting and growing revenue through net revenue retention and expansion. The company is an AI-native organization that is reinventing how Customer Success operates. The ideal candidate will have a revenue-first mindset, be excited about leading an AI-augmented team, and be comfortable with ambiguity and building processes from scratch. This role works cross-functionally with Sales, Broker Partnerships, Marketing, RevOps, Data, Product, and Legal. The preferred location is Tampa.

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 AI-augmented or agentic processes.
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 and how to drive outcomes through relationships and teams not directly controlled.
Comfort with data and systems, living in Salesforce, pulling own metrics, spotting signal in noise, and making team's 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 every level and leading QBRs, business reviews, defending renewals, and writing clear, persuasive emails.

Nice To Haves

Healthcare or benefits experience is preferred.
Hands-on experience designing AI-augmented or agentic processes is a strong plus.

Responsibilities

Own net revenue retention and gross retention, including the renewal calendar, churn-risk triage, and forecasting.
Drive expansion and product adoption by managing the upsell pipeline and product-adoption motion.
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 building the bench.
Bring retention, expansion, and engagement metrics to the table, spotting trends and turning them into action.