Head of Implementation & Customer Success
Posted Updated
Description
- This role ensures that our platform and partnerships translate into real outcomes for customers—successful deployments, strong adoption, and long-term retention
- 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
- 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
- Experience building and scaling implementation or customer success teams in high-growth environments
- 8–12+ years of experience in B2B SaaS post-sales roles (implementation, professional services, or customer success)
- Excellent communication skills, including experience engaging executive stakeholders
- Experience managing long implementation cycles with contractual deliverables and deadlines
- Experience working with government or public sector customers
- Ability to operate with high ownership in fast-paced, ambiguous environments
- Proven experience leading complex enterprise or government implementations with multiple stakeholders
- Strong program management and operational leadership capabilities
- . We value people who take ownership, experiment quickly, and use modern tools—including AI and automation—to increase their leverage and impact
- 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