HealthJoy

VP, Customer Success & Retention

Tampa, FL · Vp

Sponsorship not specifiedDetected 37 days ago

SalesforceAccount ManagementForecastingCustomer SuccessResearchLeadership

About the role

This is a commercial role, not a satisfaction role.
Net revenue retention, gross retention, and expansion are the outcomes that matter.
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.

Own net revenue retention and gross retention.
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.
Drive expansion and product adoption.
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.
Own the broker-advocacy dimension of retention.
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.
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.

8+ years in Customer Success, account management, or a commercial retention role, including team leadership.
You know what it takes to defend and grow a B2B book of business.
If you'd rather run the proven playbook you already know, this isn't the role.
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.

AI-native, or hungry to be.
This is the one that matters most.
Hands-on experience designing AI-augmented or agentic processes is a strong plus
an authentic builder's curiosity about it is non-negotiable.

Certain roles are eligible for additional cash incentives such as commission, annual bonus targets, or other variable incentives.
In addition to cash compensation, HealthJoy offers a rich "Total Rewards" package that includes:
Medical, Dental, and Vision insurance packages
HSA contribution match
Stock options for eligible roles
Paid parental leave
You make SFDC the system of record for how the team forecasts renewals, manages opportunities, and tracks the health of the book.
You think in terms of retention, expansion, and net revenue retention, not just satisfaction scores or relationship health.
You understand how broker-channel dynamics shape retention in benefits, and you know how to drive outcomes through relationships and teams you don't directly control.

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.
What We're Looking For

This listing is sourced directly from HealthJoy's careers page and normalized into a canonical job model.