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 $180,000 – $220,000, 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.