[Hiring] Director, Commercial Activation & Revenue Strategy @PeopleJoy

Role Description

As the Director of Commercial Activation & Revenue Strategy you'll be critical in designing and maintaining the operational system that turns existing customers into growing revenue assets. Working closely with the CEO and Account Manager you'll be responsible for developing playbooks for activation, renewals and internal expansion.

In this role, you'll be the CEO's strategic partner, directly collaborating to turn sales and renewals into repeatable commercial motions. Your work will be instrumental in building and scaling the company's revenue engine—and ultimately, the company's success.

• 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, SDR, Product, and RevOps so everyone sees the same picture.
• Enable the team: Coach Account Management on renewal and stakeholder politics; help SDR tighten messaging (quality > volume).

Qualifications

• 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

Requirements

• Weekly check-ins with Account Management to ensure playbooks are being followed.
• Tracking which messages and channels drive employee participation, and reporting what works.
• Designing playbooks for onboarding and SDR outreach that help accounts grow.
• Driving higher employee adoption and usage of all available benefits.
• Helping accounts expand from pilots into larger rollouts.
• Expanding Net Revenue Retention (NRR) over time.
• Supporting SDRs with better messaging and sequencing to improve new logo outreach.
• Seeing the playbooks you built being used across the team.

Benefits

• Compensation: $120,000–$150,000 (depending on experience, +variable comp)
• Equity participation
• QSEHRA, Dental, Vision, 401(k) match, Disability & Life insurance

Company Description

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

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.

• 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

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

• Do Right by Others
• Improve Every Time
• Be All-In — and Be Honest
• Win Together
• Grit