VP, Customer Success & Retention

Lets keep things simple: were 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 dont understand and dont 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 Chicagos Best Places to Work while growing globally to more than 300 team members. Were focused here on protecting and growing the revenue base weve built and on reinventing how a Customer Success organization operates in an AI-native company.

The opportunity is real and the stakes are 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 cant 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.

Youll 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 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.

Its also a building role and increasingly an AI-native one. Weve 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. Thats the starting line not the finish. Youll lead a team and a roadmap thats 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 dont 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 youll be at the center of it.

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 teams 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 teams 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 doesnt 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 cant 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.

8 years in Customer Success account management or a commercial retention role including team leadership. Youve 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. Youre genuinely excited to lead a Customer Success organization where AI and agents do the heavy lifting and youre 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 builders curiosity about it is non-negotiable. If the idea of reinventing how CS operates energizes you youll thrive here. If youd rather run the proven playbook you already know this isnt 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 dont 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 teams 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. Youll 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 clients 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.

If youre looking for a defined playbook and a steady-state book of business to manage this isnt 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 wont succeed.

If you read that and thought good thats what I want keep going.

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

Job Level: This role includes a base salary and commissions. Please email at 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

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.

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.

Dont meet every single requirement We know the confidence gap and imposter syndrome can get in the way of meeting spectacular candidates so please dont hesitate to apply wed love to hear from you.