Director of Customer Onboarding

About Playground

Playground is on a mission to make excellent child care accessible to all. We’ve built best-in-class software to manage every aspect of running a child care business. Our belief is simple: providers should focus on delivering incredible care — the kind of work that only people can do — and software should handle the rest. We’re building the child care management platform that removes the administrative burden of operating a center.

We’re at an inflection point and poised for rapid growth. We’ve recently raised millions in funding, secured several statewide contracts, and work with thousands of schools across the country. Our co-founders were recently honored as Forbes 30 Under 30.

Our team is made up of owners — people who dive into big, complex problems and love building solutions that matter. If you’re excited to help shape the onboarding experience at a fast-moving, mission-driven startup, we’d love to meet you.

About the Role:

We’re looking for a Director of Customer Onboarding to lead and scale Playground’s onboarding organization — the team responsible for ensuring every new customer’s successful transition onto our platform. This is a pivotal leadership role where you’ll define the vision, strategy, and systems that power onboarding at scale, driving a seamless experience that sets the foundation for long-term customer success.

As Director, you’ll be both strategic and operational: designing scalable frameworks, bringing clarity and organization to complex processes, developing team leaders, and partnering cross-functionally to elevate the customer journey. You’ll shape how thousands of centers experience their first moments with Playground — ensuring each one feels supported, confident, and empowered to thrive.

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 Customer Success to deliver a best-in-class onboarding experience as we scale nationwide.

What You’ll Do

• Lead & Develop a High-Performing Team: Manage, mentor, and grow a team of Onboarding Managers, fostering a culture of accountability, empathy, and continuous improvement.

• Set the Strategy: Define and execute the onboarding vision and roadmap, aligning with company goals around customer activation, adoption, and retention.

• Optimize the Process: Build and refine onboarding workflows to improve efficiency, consistency, and customer satisfaction as Playground scales.

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

• Collaborate Cross-Functionally: Partner with Product, Engineering, Sales, and CX leadership to identify friction points and drive end-to-end improvements in the customer journey.

• Measure Success: Own key onboarding KPIs — time to launch, customer satisfaction, feature adoption — and use data to inform decisions and improvements.

• Champion the Customer: Advocate for customer needs and ensure every new center’s onboarding experience reflects Playground’s values and mission.

What You Need

• 8–10+ years of experience in customer onboarding, implementation, or success at a SaaS company, including 3+ years leading teams

• Proven success scaling onboarding or implementation functions through rapid growth

• Strategic thinker with a strong operational and analytical mindset

• 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

• Experience managing onboarding for mid-market or enterprise customers

• Familiarity with early childhood education or child care management software

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

• Previous experience building an onboarding function from the ground up

Compensation

OTE: $160,000 - $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.

Learn more about our journey and co-founders Dan, Josh, and Sasha at tryplayground.com/about.