Head Start Onboarding Manager

Playground is working 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 — from billing and attendance to payroll, compliance, communication, and multi-site operations. We believe providers should focus on delivering incredible child care — the kind of work only people can do — and software should handle the rest. We’re building the child care management platform that eliminates the administrative burden of running a center.

Playground is at an inflection point and poised for rapid growth. We recently raised millions of dollars, have several statewide contracts, and now serve thousands of schools across the country. Our founders were recently recognized on Forbes 30 Under 30.

We are a team of owners who aren’t afraid to tackle large, complex projects. If you’re energized by the opportunity to help scale Playground’s implementation function and work on mission-critical enterprise projects at a high-growth startup — please apply!

• Lead Enterprise Implementations: Act as the main point of contact for enterprise clients — run kickoff calls, build project plans, define scope, manage expectations, and ensure consistent communication.

• Act as a Strategic Advisor: Help clients map their operational workflows to Playground, guide best practices, support change management, and set them up for long-term success.

• Perform Client Discovery: Conduct deep requirements gathering across multi-site operations, workflows, data structures, regulatory needs, and configuration requirements.

• Coordinate Configuration & Integrations: Oversee setup, configuration, integrations, and any data migration efforts — working closely with Product, Engineering, Support, Sales, and client-side resources.

• Manage the Project Lifecycle: Own timelines, milestones, dependencies, risks, and deliverables from start to finish.

• Build Scalable Processes: Create and maintain onboarding playbooks, templates, SOPs, and documentation to support repeatable and scalable enterprise implementations.

• Track Success Metrics: Define and monitor KPIs such as time-to-go-live, configuration accuracy, customer satisfaction, and readiness for adoption — using insights to improve processes.

• Facilitate Smooth Handoffs: Ensure a complete and documented transition from onboarding to Customer Success/Account Management.

• Collaborate Cross-Functionally: Work across Sales, Product, Engineering, Support, and CS to align on deliverables, resource needs, and client expectations.

• Head Start Ownership (As Product Launches): Become the primary owner of onboarding for Head Start customers. Manage complex, multi-location implementations involving compliance, reporting, and role-based access. Develop Head Start–specific onboarding workflows, timelines, and training materials.

• Act as a Feedback Loop to Product and Engineering on Head Start: Support the creation of a repeatable, scalable onboarding model for large programs and feature gaps and edge cases.

• Experience working with Head Start child care programs

• 3–6+ years experience in SaaS onboarding, implementation, professional services, or customer success—ideally supporting enterprise or multi-entity clients

• Strong project coordination skills with the ability to manage complex workflows and competing priorities

• Excellent written and verbal communication skills, with the ability to translate technical and business requirements into clear action

• Customer-centric, consultative mindset with the ability to understand business processes and guide clients toward optimal solutions

• Technical aptitude — familiarity with data migration, integrations, and configuration, plus comfort working with technical teams

• Experience creating documentation, templates, and playbooks to support scalable processes

• Ability to manage multiple concurrent implementation projects in a fast-paced environment

• Experience with vertical SaaS, regulated industries, or multi-site operational environments

• Background onboarding enterprise or multi-entity customers with custom configuration needs

• Familiarity with training enablement or user-education content creation

• Analytical mindset with experience defining KPIs and tracking process improvements

• Enterprise clients go live predictably and efficiently, with short time-to-value

• Projects deliver on time, within scope, with accurate configuration and minimal post-go-live issues

• Clients express high satisfaction with onboarding and feel confident using Playground

• Scalable and repeatable onboarding processes (SOPs, templates, playbooks) are in place

• Strong alignment across internal teams with smooth communication and minimal friction

• Measurable improvements in client adoption, retention, and long-term success

As Playground onboards larger, multi-site, and more complex clients, our implementations require greater depth, structure, and coordination. Without a dedicated enterprise specialist, we risk misconfiguration, delays, poor adoption, or unsustainable load on generalist teams. This role ensures each enterprise client receives the rigor and attention needed to unlock value quickly, reduce churn risk, and support scalable long-term growth.

Salary for this position is $105,000 OTE, subject to standard withholding and applicable taxes. Actual compensation will be based on skills, experience, potential impact, market demands, and location.

• Competitive salary + equity

• 3 weeks of PTO

• Health, vision, and dental benefits

• $1200/year education stipend

• 401(k)

• Free lunch daily

• New Macbook

• Collaborative and supportive work culture with a high level of autonomy and room for growth

• Help accelerate our mission to make excellent childcare accessible to all!

How to Apply: If you're a hustler who's excited to join a mission-driven, early-stage company with ownership, craftsmanship, and empathy at the center of what we do, apply now. The Playground Team is fully in-office in either our Union Square NYC Office or our LoDo, Denver Office. Please make sure you are open to a fully in-person role before applying.

Check out: https://www.tryplayground.com/about to learn more about our journey and co-founders Dan, Josh, and Sasha.