Head of Account Management and Customer Success

PeopleJoy customizes and fully administers education benefits that help employers attract and retain talent — through commitment, creativity, and scalable administration.

As workforce expectations shift toward personalization, continuous skilling, and community, PeopleJoy helps employers meet the moment. We deliver education and student loan benefits as a fully managed service that drives real impact for employees and employers alike.

About Our Culture

Our culture is what makes PeopleJoy a great place to do meaningful work. We come from diverse backgrounds and experiences, but we're united by a shared drive to help others and improve lives.

We

• Put customers first and strive to exceed expectations
• Embrace change and adapt quickly
• Take accountability for our work and our outcomes
• Value trust, respect, and follow-through
• Focus on meaningful results, not just chasing numbers

Here, you'll find purpose, ownership, and a team that values progress over perfection.

Our Core Values

Our values shape our vision, products, culture, and customer success:

Do Right By Others

Have people's backs. Be someone others can rely on.

Improve Every Time

We don't do the same work the same way twice. We constantly streamline, simplify, and automate so each iteration is faster and better.

Be All-In — and Be Honest

We act in the best interest of PeopleJoy's mission and long-term success. We show up fully, take responsibility, and raise our hands early if something feels out of alignment.

Win Together

We prioritize team success over individual comfort, take feedback with humility, and step into whatever role helps the team win today.

Grit

We commit to long-term goals with resilience and discipline, pushing through obstacles even when progress feels slow.

About The Opportunity

As the Head of Account Management and Customer Success you'll be critical in designing and maintaining the operational system that turns existing customers into growing revenue assets. Working closely with the Client Success and Account Management teams you'll be responsible for developing playbooks for activation, renewals and internal expansion. You'll also maintain and analyze metrics related to our sales funnel and client engagement to continually refine and improve our sales conversions and increase net revenue retention.

In this role, you'll be the CEO's strategic partner, directly collaborating to turn sales and renewals into repeatable commercial motions. This means studying adoption/usage dynamics, and renewal politics and building playbooks. Your work will be instrumental in building and scaling the company's revenue engine—and ultimately, the company's success.

Job Details

• Title: Head of Account Management and Customer Success
• Compensation: $120,000–$150,000 (depending on experience, +variable comp)
• Equity participation
• QSEHRA, Dental, Vision, 401(k) match, Disability & Life insurance
• Reports To: CEO
• Location: Work where youʼre most effective but must be able to come to our Philadelphia office for whiteboard sessions.
• Job Type: Full-Time

What does a Head of Account Management and Customer Success do, anyway? In simple terms, they help generate more revenue from current customers by getting employees to use the benefit and stick with it.

Here's What That Looks Like Day-to-day

• Set the big goals: Own NRR targets and map the steps needed to hit them.
• Activate customers: Build playbooks for onboarding and driving employee participation.
• Remove friction: Spot blockers early (messaging, HR Ops, timing) and clear them.
• Grow usage → grow accounts: Work with HR Ops/Comms to roll out benefits, send emails/SMS, run webinars, and increase adoption.
• Drive renewals + expansion: Create QBR and renewal templates tied to budget cycles; help convert pilots (ex. clinical) into bigger rollouts (ex. all-staff).
• Connect the dots internally: Loop between Sales, CS, AM, Product, and RevOps so everyone sees the same picture.
• Enable the team: Coach Account Management on renewal and stakeholder politics.

If this sounds like you, your previous education, work experience, and passions probably sound like you've:

• Operated in B2C SaaS sales or adjacent categories (benefits, financial wellness, workforce, education, behavioral health, navigation, talent mobility)
• Worked in early-stage revenue environments pre-CRO and helped them scale
• Scaled usage/activation → renewal → expansion → NRR motions
• Experienced founder-led sales and non-linear buyer sequences
• Navigated CHRO, Total Rewards, HR Ops, and Finance stakeholder dynamics
• Built commercial playbooks before inheriting them

What Success Looks Like For You

• You're running weekly check-ins with Account Management to make sure playbooks are being followed.
• You're tracking which messages and channels drive employee participation, and you're reporting what works.
• You're designing playbooks for onboarding and outreach that help accounts grow.
• You're driving higher employee adoption and usage of all available benefits.
• You're helping accounts expand from pilots into larger rollouts.
• You're expanding Net Revenue Retention (NRR) over time.
• You're seeing the playbooks you built being used across the team.