Head of Implementation & Customer Success
Wonderschool · San Francisco
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.