Head of Implementation & Customer Success at Wonderschool

<h3><strong>About Wonderschool</strong></h3> <p>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.</p> <p>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.</p> <p>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.</p> <p>This role ensures that our platform and partnerships translate into real outcomes for customers - successful deployments, strong adoption, and long-term retention.</p> <h3><strong>Position Summary</strong></h3> <p>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 &amp; Customer Success is responsible for ensuring complex deployments are executed successfully, customers achieve measurable outcomes, and the business captures durable, recurring revenue.</p> <p>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.</p> <h3><strong>Responsibilities</strong></h3> <h4><strong>Own Implementation &amp; Customer Outcomes</strong></h4> <ul> <li>Own end-to-end delivery of government and enterprise implementations, from kickoff through go-live and post-launch success</li> <li>Ensure customers achieve defined outcomes, including successful deployment, adoption, and ongoing usage</li> <li>Manage complex, multi-stakeholder implementations involving integrations, data migration, and system configuration</li> <li>Establish clear success metrics across adoption, retention, and expansion</li> </ul> <h4><strong>Build a Scalable Customer Success Engine</strong></h4> <ul> <li>Design and implement repeatable playbooks for onboarding, implementation, and long-term customer success</li> <li>Develop systems to monitor customer health, identify risks, and drive proactive engagement</li> <li>Build frameworks that improve time-to-value and increase net revenue retention</li> <li>Identify opportunities for expansion and deeper customer partnerships</li> </ul> <h4><strong>Lead and Scale the Team</strong></h4> <ul> <li>Build and lead a high-performing implementation and customer success organization</li> <li>Define roles, hiring plans, and operating structure as the company scales</li> <li>Coach and develop team members while maintaining high standards of execution</li> <li>Establish clear performance expectations tied to customer and business outcomes</li> </ul> <h4><strong>Drive Cross-Functional Execution</strong></h4> <ul> <li>Partner closely with Product, Engineering, and Sales to ensure successful deployments and product alignment</li> <li>Translate customer feedback into product improvements and roadmap priorities</li> <li>Ensure alignment between sales commitments and delivery capabilities</li> <li>Advocate for scalable solutions over one-off implementations</li> </ul> <h4><strong>Manage Executive Stakeholders</strong></h4> <ul> <li>Build strong relationships with customer leadership and executive stakeholders</li> <li>Lead high-stakes conversations during implementations and critical phases</li> <li>Navigate complex challenges while maintaining trust and alignment</li> <li>Communicate clearly across internal and external stakeholders</li> </ul> <h3><strong>Required Qualifications</strong></h3> <ul> <li>8–12+ years of experience in B2B SaaS post-sales roles (implementation, professional services, or customer success)</li> <li>Proven experience leading complex enterprise or government implementations with multiple stakeholders</li> <li>Experience building and scaling implementation or customer success teams in high-growth environments</li> <li>Strong program management and operational leadership capabilities</li> <li>Experience managing long implementation cycles with contractual deliverables and deadlines</li> <li>Excellent communication skills, including experience engaging executive stakeholders</li> <li>Ability to operate with high ownership in fast-paced, ambiguous environments</li> </ul> <h3><strong>Preferred Qualifications</strong></h3> <ul> <li>Experience working with government or public sector customers</li> <li>Background in enterprise SaaS, professional services, or consulting</li> <li>Experience owning or influencing net revenue retention (NRR)</li> <li>Familiarity with regulated industries (education, healthcare, public sector)</li> <li>Experience building systems that improve operational efficiency and scalability</li> </ul> <h3><strong>Compensation &amp; Benefits</strong></h3> <p>Compensation Range (California):<br>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.</p> <p>Wonderschool offers a competitive benefits package, including:</p> <ul> <li>Health benefits with up to 100% coverage for employee premiums and up to 80% for dependents</li> <li>Wifi and employee wellness stipends</li> <li>Flexible PTO, paid holidays, and mental wellness days</li> <li>Competitive parental leave (eligible after 6 months of employment)</li> <li>A highly collaborative, mission-driven workplace environment</li> </ul> <h3><strong>Location / Travel Expectations</strong></h3> <p>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.</p>