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 managing long implementation cycles with contractual deliverables and deadlines Excellent communication skills including experience engaging executive stakeholders Ability to operate with high ownership in fast-paced ambiguous environments Preferred Qualifications Experience working with government or public sector customers Background in enterprise SaaS professional services or consulting Experience owning or influencing net revenue retention (NRR) Familiarity with regulated industries (education healthcare public sector) Experience building systems that improve operational efficiency and scalability Compensation & Benefits Compensation Range (California) The base salary range for this role is $180000 – $220000 depending on experience skills and location. This role may also be eligible for equity and other forms of compensation. Wonderschool offers a competitive benefits package including Health benefits with up to 100% coverage for employee premiums and up to 80% for dependents Wifi and employee wellness stipends Flexible PTO paid holidays and mental wellness days Competitive parental leave (eligible after 6 months of employment) A highly collaborative mission-driven workplace environment Location / Travel Expectations This role is based in our office in Rincon Hill San Francisco 5-6 days a week in office. Regular travel is required to support customer implementations key partnerships and critical deployment phases.