Head of Implementation & Customer Success · Wonderschool

Fri, 17 Apr 2026 13:09:14 GMT
Operations

Wonderschool · San Francisco · $180,000 – $220,000 · hybrid
Head of Implementation & Customer Success Wonderschool is a company that empowers small business owners to launch and grow childcare programs through software, coaching, and support. We are looking for a Head of Implementation & Customer Success to join our team. As a Head of Implementation & Customer Success, you will be responsible for ensuring that our platform and partnerships translate into real outcomes for customers. This includes successful deployments, strong adoption, and long-term retention. Responsibilities: * 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 San Francisco (hybrid, approximately three days per week in office). * Regular travel is required to support customer implementations, key partnerships, and critical deployment phases.