Head of Implementation & Customer Success

Head of Implementation & Customer Success

Wonderschool is a company that empowers small business owners to launch and grow childcare programs through software, coaching, and support. We are looking for a Head of Implementation & Customer Success to join our team.

As a Head of Implementation & Customer Success, you will be responsible for ensuring that our platform and partnerships translate into real outcomes for customers. This includes successful deployments, strong adoption, and long-term retention.

Responsibilities:

• 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 San Francisco (hybrid, approximately three days per week in office).
• Regular travel is required to support customer implementations, key partnerships, and critical deployment phases.