Enterprise Onboarding & Implementation Specialist

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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.

• 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.

• 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.…