Head of Implementation & Customer Success

The role

Own the full post-sale lifecycle for government and enterprise customers, from implementation through retention and expansion. Lead the implementation and customer success team and build the playbooks and systems to scale it.

What you will do

• 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 deployment, adoption and ongoing usage
• Manage complex, multi-stakeholder implementations involving integrations, data migration and system configuration
• 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 and lead a high-performing implementation and customer success organization
• Partner with Product, Engineering and Sales to ensure successful deployments and product alignment
• Translate customer feedback into product improvements and roadmap priorities
• Build relationships with customer leadership and executive stakeholders
• Lead high-stakes conversations during implementations and critical phases

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

Nice to have

• 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

Benefits

• 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)
• Collaborative, mission-driven workplace environment

Before you apply

• Regular travel is required to support customer implementations and deployment phases

About the company

Wonderschool helps childcare providers launch and grow programs through software, coaching and support, and partners with governments to modernize childcare infrastructure. Its platform covers enrollment, marketing, licensing, compliance and daily operations.