Head of Implementation & Customer Success

About Wonderschool

Wonderschool’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 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.

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.

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.