Manager of 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: Onboarding Manager
We’re looking for a Manager of Onboarding to lead and grow Playground’s onboarding function — the team responsible for welcoming new customers and ensuring their successful transition onto our platform. This is a high-impact leadership role where you’ll manage a team of Onboarding Managers, refine our onboarding strategy, and design scalable systems that drive customer success from day one.
As the Onboarding Manager’s manager, you’ll be both strategic and hands-on: coaching team members, optimizing processes, and partnering cross-functionally to continuously improve the customer journey. You’ll help shape the first impression every new customer has of Playground — ensuring each center feels supported, confident, and ready to thrive on our platform.
This is an in-person role based in our NYC office, where you’ll work closely with Product, Engineering, Sales, and Customer Success teams to deliver an exceptional onboarding experience at scale.
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
4+ years in customer onboarding, implementation, or customer success at a SaaS company, with 1–2 years in a leadership or people management role
A proven track record of building or scaling onboarding programs and processes
Excellent communication and coaching skills — you know how to inspire and develop others
Strong operational and analytical mindset with the ability to manage multiple priorities
Experience working cross-functionally in a fast-paced, startup environment
High attention to detail and comfort driving both strategic and tactical initiatives
Nice-to-Haves
Experience managing onboarding teams serving mid-market or enterprise clients
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: $110,000
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
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 at Union Square, NYC. Please apply only if you're open to an in-person role.
Learn more about our journey and co-founders Dan, Josh, and Sasha at tryplayground.com/about.
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