Director of Customer Success

About the Role
We’re looking for a Director of Customer Success to lead and scale a team of Customer Success Managers responsible for driving long-term retention and adoption across Playground’s growing customer base. This is a critical leadership role where you’ll own the strategy, execution, and day-to-day performance of the CSM team, ensuring every center on Playground feels supported, sees measurable value and grows with us over time.
As Manager, you’ll balance strategy and execution: refining scalable processes, developing your team, and partnering cross-functionally to deepen customer relationships and reduce churn. You’ll play a key role in shaping how thousands of centers experience ongoing partnership with Playground — turning satisfied customers into passionate advocates.

This is an in-person role based in our Union Square, NYC or LoDo, Denver office, where you’ll collaborate closely with Product, Engineering, Sales, and Onboarding to deliver a best-in-class post-launch customer experience as we continue to scale nationwide.

What You’ll Do

• Lead & Develop a High-Performing Team: Manage, mentor, and grow a team of Customer Success Managers, fostering a culture of accountability, curiosity, and customer obsession.

• Own Retention & Growth: Drive net revenue retention and logo retention across the book of business — coaching CSMs on renewal strategy and commercial conversations.

• Drive Strategy & Execution: Partner with leadership to define and execute the CS vision and roadmap, aligning with company goals around retention, adoption, and customer lifetime value.

• Optimize the Customer Journey: Build and refine post-onboarding workflows, health scoring, and engagement cadences to improve consistency and proactive outreach as Playground scales.

• Coach & Empower: Provide regular feedback, training, and performance management to ensure every CSM delivers an exceptional, consultative customer experience.

• Measure Success: Track key CS KPIs — net revenue retention, NPS, health scores, feature adoption, time-to-value — and use data to inform decisions and improvements.

• Champion the Customer: Serve as the voice of the customer at the leadership table, advocating for their needs and ensuring Playground’s post-launch experience reflects our values and mission.

What You Need

• 3–5+ years of experience in Customer Success, Account Management, or a related customer-facing role at a SaaS company, including 2+ years leading teams

• Proven success managing and scaling a CS function through periods of growth, with a track record of hitting retention targets

• Strategic thinker with a strong operational and analytical mindset — comfortable building dashboards, interpreting data, and using metrics to drive decisions

• Excellent leadership, communication, and coaching skills — you know how to inspire, motivate, and grow others

• Experience driving cross-functional initiatives in fast-paced or startup environments

• Data-driven decision maker with a bias toward action and continuous improvement

Nice-to-Haves

• Familiarity with early childhood education or child care management software

• Background in education, non-profits, or mission-driven organizations

• Previous experience building or refining CS playbooks, health scoring models, or scaled engagement programs from the ground up

Compensation
OTE: $170,000-200,000 Base salary + variable compensation, subject to standard withholdings and taxes. Actual compensation will depend on experience, location, and interview performance.

Why Join Playground

• Competitive salary + equity

• 3 weeks of PTO

• Health, vision, and dental benefits

• $1,200/year education stipend

• 401(k)

• Free lunch daily

• High-autonomy, high-ownership team culture

• A meaningful mission with real-world impact

How to Apply
If you’re excited to join a mission-driven, early-stage company where craftsmanship, ownership, and empathy are core values, we want to hear from you. The Playground Team is fully in-office in Union Square, NYC and LoDo, Denver offices. Please make sure you are open to a fully in-person role before applying.