Head of Implementation & Customer Success

About Wonderschool

Wonderschool is building the future of child care by providing technology and operational infrastructure that helps providers run sustainable businesses while helping governments modernize how they support families and child care systems.

Our platform enables providers to launch and grow programs, helps parents find care, and equips governments with tools and data to administer child care initiatives at scale.

We are seeking a Head of Implementation & Customer Success to lead the full post-sale lifecycle for Wonderschool’s government and enterprise customers—from implementation through long-term retention and expansion. This role is responsible for ensuring successful deployments, driving product adoption, and building a scalable customer success function as the company continues to grow.

This leader will operate as a player-coach, personally leading high-stakes implementations while building the processes, team structure, and operational frameworks required to scale the function. The role requires strong cross-functional collaboration with Product, Engineering, Sales, and executive leadership to ensure customer outcomes are achieved and insights from the field inform product development.

Responsibilities

Implementation Leadership

• Own the end-to-end implementation process for government and enterprise deployments
• Lead complex multi-month rollouts involving multiple stakeholders, data migrations, integrations, and system configuration
• Develop repeatable implementation playbooks, frameworks, and project plans
• Ensure successful go-live readiness and post-launch support for customers

Customer Success & Retention

• Drive customer adoption, engagement, and long-term success with Wonderschool’s platform
• Establish and track key customer success metrics such as adoption, retention, and expansion
• Build strong relationships with customer leadership teams and key stakeholders
• Identify opportunities for expansion and long-term partnership growth

Team Building & Organizational Development

• Build and lead a high-performing implementation and customer success team
• Define team roles, hiring plans, and operational processes
• Coach and mentor team members while maintaining high standards of execution
• Establish scalable frameworks for onboarding, implementation, and ongoing customer success

Cross-Functional Leadership

• Partner closely with Product, Engineering, and Sales to ensure successful deployments and product alignment
• Translate customer feedback and operational insights into product improvements
• Advocate for customer needs while balancing business priorities and product development timelines

Executive Communication & Stakeholder Management

• Communicate clearly with executive stakeholders across customer organizations
• Navigate complex implementation challenges and manage high-stakes client conversations
• Ensure alignment across internal teams and customer leadership during critical deployment phases

Required Qualifications

• 8–12+ years of experience in B2B SaaS post-sales roles including implementation, professional services, or customer success
• Experience leading complex enterprise or government deployments with multiple stakeholders
• Proven ability to build and scale implementation or customer success teams in growth-stage companies
• Strong program management and operational leadership skills
• Experience managing long implementation timelines with contractual deliverables and deadlines
• Excellent communication skills with the ability to engage executive stakeholders
• Experience collaborating cross-functionally with Product, Engineering, and Sales teams
• Ability to thrive in fast-paced environments with high ownership and ambiguity

Preferred Qualifications

• Experience working with government agencies or public sector customers
• Experience leading professional services or implementation teams in enterprise SaaS companies
• Background in consulting or government-focused SaaS environments
• Experience managing net revenue retention (NRR) or similar post-sales metrics
• Familiarity with regulated industries such as education, healthcare, or public sector technology

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 focused on impact and growth

Location

This role is based in the San Francisco Bay Area with a hybrid work schedule (approximately three days per week in office).