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Director of Customer Success

Playground, Denver, CO, United States


About the Role We’re looking for a Manager 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: $130,000 – $160,000 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.

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