Head of Implementation & Customer Success
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.
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.
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