Head of Implementation & Customer Success

About Wonderschool Wonderschool’s mission is to ensure every child has access to early childhood education that helps them realize their full potential. We empower small business owners - childcare providers - to launch and grow programs through software, coaching, and support, while partnering with governments to modernize childcare infrastructure. We are building a category-defining platform at the intersection of marketplace, SaaS, and public sector systems - now increasingly powered by AI. Our products help providers run and grow their businesses, from enrollment and marketing to licensing, compliance, and daily operations. Our team is small, fast-moving, and deeply focused on building systems that scale. We value people who take ownership, experiment quickly, and use modern tools - including AI and automation - to increase their leverage and impact. This role ensures that our platform and partnerships translate into real outcomes for customers - successful deployments, strong adoption, and long-term retention. Position Summary This role owns the full post-sale lifecycle for Wonderschool’s government and enterprise customers - from implementation through long-term retention and expansion. The Head of Implementation & Customer Success is responsible for ensuring complex deployments are executed successfully, customers achieve measurable outcomes, and the business captures durable, recurring revenue. Operating as both a strategic leader and hands-on operator, this role builds the systems, playbooks, and team required to scale implementation and customer success across multiple markets. Success in this role directly impacts customer outcomes, product adoption, and long-term contract renewals. Responsibilities Own Implementation & Customer Outcomes Own end-to-end delivery of government and enterprise implementations, from kickoff through go-live and post-launch success Ensure customers achieve defined outcomes, including successful deployment, adoption, and ongoing usage Manage complex, multi-stakeholder implementations involving integrations, data migration, and system configuration Establish clear success metrics across adoption, retention, and expansion Build a Scalable Customer Success Engine Design and implement repeatable playbooks for onboarding, implementation, and long-term customer success Develop systems to monitor customer health, identify risks, and drive proactive engagement Build frameworks that improve time-to-value and increase net revenue retention Identify opportunities for expansion and deeper customer partnerships Lead and Scale the Team Build and lead a high-performing implementation and customer success organization Define roles, hiring plans, and operating structure as the company scales Coach and develop team members while maintaining high standards of execution Establish clear performance expectations tied to customer and business outcomes Drive Cross-Functional Execution Partner closely with Product, Engineering, and Sales to ensure successful deployments and product alignment Translate customer feedback into product improvements and roadmap priorities Ensure alignment between sales commitments and delivery capabilities Advocate for scalable solutions over one-off implementations Manage Executive Stakeholders Build strong relationships with customer leadership and executive stakeholders Lead high-stakes conversations during implementations and critical phases Navigate complex challenges while maintaining trust and alignment Communicate clearly across internal and external stakeholders Required Qualifications 8–12+ years of experience in B2B SaaS post-sales roles (implementation, professional services, or customer success) Proven experience leading complex enterprise or government implementations with multiple stakeholders Experience building and scaling implementation or customer success teams in high-growth environments Strong program management and operational leadership capabilities Experience man