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: $170000-200000 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

• $1200/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.

What We Do

For too long child care programs have been stuck with clunky tools and manual processes falling behind while other industries get all the high-tech toys.Playground is flipping the script. Playground is a proven platform for child care providers to streamline their operations reclaim their time and get back to the joy of teaching and caring. Our all-in-one child care management software manages billing attendance registration and enrollment communication paperwork payroll and more.

Why Work With Us

At Playground we’re a mission-driven high-growth startup where collaboration creativity and entrepreneurial thinking fuel everything we do. We act like owners take initiative and make smart decisions independently every day. Join us to make an impact grow fast and be part of a team that truly values your ideas energy and drive.

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