VP, Customer Success & Retention

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 owned a retention or net revenue retention number and led the people responsible for delivering it. You know what it takes to defend and grow a B2B book of business.

Revenue-first mindset. You think in terms of retention, expansion, and net revenue retention, not just satisfaction scores or relationship health. You connect every CS activity to a business outcome and you hold yourself and your team accountable to the number.

AI-native, or hungry to be. This is the one that matters most. You're genuinely excited to lead a Customer Success organization where AI and agents do the heavy lifting, and you're comfortable building and iterating on those workflows rather than waiting for someone to hand them to you. Hands-on experience designing AI-augmented or agentic processes is a strong plus; an authentic builder's curiosity about it is non-negotiable. If the idea of reinventing how CS operates energizes you, you'll thrive here. If you'd rather run the proven playbook you already know, this isn't the role.

Commercial and cross-functional fluency. You operate comfortably with Sales, Marketing, RevOps, Data, Product, and Legal. 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.

Comfort with data and systems. You live in Salesforce, you pull your own metrics, you spot the signal in the noise, and you make the team's reporting a source of truth the whole business can rely on.

Comfort with ambiguity. This is a function in transformation, not a steady-state book to maintain. You'll build things from scratch, change how the work is done, and shape the role as you go.

Executive presence and clarity. You communicate well at every level, from a CSM to a client's CHRO to our executive team. You can run a QBR, lead a business review, defend a renewal, and write a clear, persuasive email.

Healthcare or benefits experience preferred. Not required, but a real head start. Strong commercial CS leadership and genuine curiosity about the space will get you there.

This Role Is Not for Everyone

If you're looking for a defined playbook and a steady-state book of business to manage, this isn't it. If your best work comes from relationship maintenance without a retention or expansion target, look elsewhere. If AI feels like a threat or a distraction rather than the most exciting lever you have, the direction here will frustrate you. If you need full certainty before acting, or a manager telling you exactly what to do next, you won't succeed.

If you read that and thought good, that's what I want, keep going.

Reporting & Team

This role reports to the Chief Growth Officer and leads the Customer Success organization, a team of experienced CS managers and their CSMs. You'll work closely with Sales, the broker partnership team, Marketing, RevOps, Data, Product, and Legal, and you'll have visibility into senior leadership as you shape the future of Customer Success at HealthJoy.

Total Rewards

Job Level: This role includes a base salary and commissions.  Please email at hr@healthjoy.com to request the overall compensation.

The cash compensation above includes base salary only. Certain roles are eligible for additional cash incentives such as commission, annual bonus targets, or other variable incentives.

HealthJoy maintains a comprehensive strategy to determine rewarding and competitive packages for individual compensation for new hires, internal promotions, and internal job changes. This strategy is based on several factors unique to each individual, including: 1) the skills, experience, and qualifications of the individual; 2) the responsibilities and demands of the role; 3) analysis of external market data; and 4) company budget and financial performance.

While HealthJoy is a remote-first employer, certain roles we prefer to be in the Tampa Bay area, where much of our leadership resides.

The disclosed range estimate has not been adjusted for the applicable geographic differential associated with the location at which the position may be filled.

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
• 401k match
• Paid parental leave
• Company-sponsored Short Term and Long Term Disability coverage
• Flexible PTO

Commitment to Equal Pay

At HealthJoy, we are committed to creating a diverse and inclusive workplace where everyone has the opportunity to succeed and thrive.

We believe that everyone should be paid based on their qualifications, experience, and the work that they do, not on their gender, race, or any other personal characteristic. We conduct thorough annual reviews of employee pay and our pay practices to ensure we reward the right behaviors and are providing equal pay for equal work.

Commitment to Equal Opportunity

HealthJoy is committed to creating a diverse environment and is proud to be an equal opportunity employer.

All qualified applicants receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or any other basis forbidden under federal, state, or local law.

Don't meet every single requirement? We know the confidence gap and imposter syndrome can get in the way of meeting spectacular candidates, so please don't hesitate to apply, we'd love to hear from you.