VP, Customer Success & Retention

About this role

Preferred Location: Tampa

Come for the mission. Stay for the innovation.

Let's keep things simple: we're a talented, hard-working, and compassionate team driving towards a mission that impacts every single one of us.

Healthcare benefits are complex, underutilized, and often invisible to the people who need them most. Employers invest heavily in benefits their people don't understand and don't use, and when that happens, the client questions the value and the relationship is at risk. HealthJoy sits right at that intersection: we make benefits simple, connected, and worth coming back to, and our Customer Success team is the engine that turns that value into retained and expanded revenue.

HealthJoy has garnered workplace awards from Inc.'s Fastest Growing Startups and Built In Chicago's Best Places to Work while growing globally to more than 300 team members. We're focused here on protecting and growing the revenue base we've built, and on reinventing how a Customer Success organization operates in an AI-native company.

The opportunity is real and the stakes are clear. Net revenue retention is the number that compounds everything else we do. We have a strong, experienced CS team, a maturing data foundation, and a head start on AI-powered customer lifecycle tooling that most of our competitors can't match. Your job is to take that foundation and run: defending revenue, driving expansion, and building the agentic Customer Success motion that lets us manage growing books of business without growing headcount at the same rate.

The Role

You'll own Customer Success and the retention number that comes with it. That means two things at once: protecting and expanding revenue across our employer client base, and leading the team that owns those relationships through a genuine shift in how the work gets done.

This is a commercial role, not a satisfaction role. Net revenue retention, gross retention, and expansion are the outcomes that matter. You own the renewal calendar, the churn-risk triage, the upsell and product-adoption motion, and the health of every client relationship from launch through renewal. You manage the function out of Salesforce, you know your book cold, and you can tell anyone in the company exactly where retention is being made or lost and why.

It's also a building role, and increasingly an AI-native one. We've already built and deployed agents that recaptured over a thousand hours of CSM prep time in a single quarter, collapsed upsell research from hours to seconds, and replaced a six-figure vendor contract with an in-house tool. That's the starting line, not the finish. You'll lead a team and a roadmap that's moving toward a fully agentic customer lifecycle: specialized agents mapped to each phase of the client journey, triggered by real-time signals, orchestrated for the right message at the right moment. You don't have to have personally built that before, but you have to be genuinely excited to lead an organization that operates this way and to roll up your sleeves in the work.

This role works cross-functionally with Sales, the Broker Partnership team, Marketing, RevOps, Data, Product, and Legal. Retention is a team sport here, and you'll be at the center of it.

What You'll Do

Own net revenue retention and gross retention. You carry the retention number. You own the renewal calendar, knowing which accounts sit in the triage window and which are in the danger zone, and you build the forecasting discipline to see churn coming before it happens. You concentrate the team's human attention where relationship complexity and revenue impact are highest.

Drive expansion and product adoption. Retention and growth are two sides of the same book. You own the upsell pipeline and the product-adoption motion, getting live clients to activate the products that make them stickier and prove ROI. You set the targets, build the tracking, and hold the team to the outcome.

Lead the AI-native transformation of Customer Success. You own and advance the agentic customer lifecycle roadmap: business-review and renewal-proposal agents, upsell-discovery agents, long-tail automated outreach, predictive health scoring, and the orchestration layer that ties them together. You partner with Data, Product, and RevOps to keep the underlying data foundation trustworthy, and you make AI a multiplier for your team's judgment rather than a replacement for it.

Run the team out of Salesforce. You make SFDC the system of record for how the team forecasts renewals, manages opportunities, and tracks the health of the book. You bring rigor and a single source of truth to how Customer Success operates day to day.

Own the broker-advocacy dimension of retention. A large share of churn risk concentrates in accounts where the broker doesn't actively sell renewal value. You partner with the broker partnership team and Sales to close that gap, equipping brokers with renewal narratives, benchmarks, and ROI proof, and reaching clients directly where broker pass-through can't be assumed.

Be the senior voice for clients. You show up for the relationships that matter: QBRs, business reviews, escalations, on-site visits, and incident communications. You own the Customer Advisory Board and the Voice of Customer program, and you bring what you hear back into Product, Marketing, and the broader business.

Lead and develop the team. You manage a team of CS managers and their CSMs, you raise the commercial sophistication of the org, and you build the bench. As books grow and the work gets more strategic, you make sure your people are spending their time on judgment, not busywork.

Bring the numbers to the table. You know your retention, expansion, and engagement metrics cold, you spot the trends, and you turn them into action without waiting for a data team to hand you the answer.

What We're Looking For

8+ years in Customer Success, account management, or a commercial retention role, including team leadership. You've own

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