Head of Implementation & Customer Success

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, profes