Director of Onboarding

We’re looking for a Director of Customer Onboarding to lead and scale a team of Onboarding Managers responsible for ensuring every new customer’s successful transition onto our platform. This is a critical leadership role where you’ll drive the strategy, execution, and day-to-day performance of onboarding — creating a seamless experience that sets the foundation for long-term customer success.

As Manager, you’ll balance strategy and execution: refining scalable processes, developing your team, and partnering cross-functionally to elevate the customer journey. You’ll play a key role in shaping 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 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.

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

Drive Strategy & Execution: Partner with leadership to 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: Track 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.

• 3–5+ years of experience in customer onboarding, implementation, or success at a SaaS company, including 2+ years leading teams

• Proven success supporting or scaling onboarding or implementation functions through periods of 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

• Familiarity with early childhood education or child care management software

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

• Previous experience helping build or refine an onboarding function

$170,000 to $200,000
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 LoDo, Denver offices. Please make sure you are open to a fully in-person role before applying.