Head of Implementation & Customer Success

We Love AI Jobs; San Francisco (CA); On-site; USD 180,000 - 220,000; Full time

Job summary

Wonderschool is seeking a Head of Implementation & Customer Success to own post-sale delivery for government and enterprise customers. You will lead complex deployments, build scalable implementation and retention processes, and develop a high-performing team responsible for long-term customer success.

This is an on-site, permanent role requiring 8–12+ years of experience. You will own end-to-end delivery from kickoff through go-live and post-launch success, design repeatable onboarding and

Qualifications

• 8–12+ years of post-sale leadership experience.
• Proven track record leading government/enterprise deployments.
• Strong cross-functional collaboration and stakeholder management.
• Experience designing scalable playbooks and health-monitoring systems.

Responsibilities

• Own end-to-end government and enterprise implementations from kickoff to post-launch success.
• Build repeatable onboarding, implementation, and customer success playbooks and health monitoring systems.
• Lead and scale the implementation and customer success organization.
• Partner with Product, Engineering, and Sales to ensure delivery aligns with roadmap and commitments.
• Manage executive stakeholder relationships during deployments and critical phases.

Skills

B2B SaaS

Implementation management

Customer success

Program management

Data migration

System integrations

Customer health metrics

Net revenue retention

Job description

The Head of Implementation & Customer Success owns post-sale delivery and customer outcomes for Wonderschool’s government and enterprise customers. The role leads complex deployments, builds scalable implementation and retention processes, and develops the team responsible for long-term customer success.* Permanent* On-site* 8–12+ years### Skills and expertiseB2B SaaSImplementation managementCustomer successProgram managementData migrationSystem integrationsCustomer health metricsNet revenue retention### Key responsibilities* Own government and enterprise implementations from kickoff through launch and ongoing customer outcomes.* Build repeatable onboarding, implementation, and customer success playbooks and health monitoring systems.* Lead and scale the implementation and customer success organization.## How this job comparesCompared with 56 open director customer success jobs on October 10, 2026.Pay: This job pays $180K to $220K a year. The 28 open director customer success jobs that publish US pay start at $167K on average, so this job starts about 8% higher.Similar open jobs: We Love AI Jobs lists 56 open director customer success jobs at 45 companies.Remote work: This job is on site. 12 of the 56 director customer success jobs (21%) are remote.AI in this role: Medium. The role uses AI tools and works with AI systems as a regular part of the job. The company describes AI and automation as tools for increasing team leverage, and the role is expected to use modern tools. Its primary work remains customer implementation, adoption, and retention rather than building AI systems.## Full descriptionAbout WonderschoolWonderschool’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 SummaryThis 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.ResponsibilitiesOwn 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 expansionBuild 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 partnershipsLead 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 outcomesDrive 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 implementationsManage 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