Head of Implementation & Customer Success
WonderschoolSan Francisco, California, United States · Posted 5 months agoDescription
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.
Similar jobs
Est. 200,000 USD
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 an…
Est. 150,000 USD
Provider Growth & AI Agent Operations Lead Location: San Francisco (Rincon Hill) Company Overview Mission: Make high-quality early childhood education accessible to all by empowering childcare providers with tools an…
Est. 140,000 USD
The Opportunity Wonderschool is building the first integrated platform for early childhood education - used by providers, families, and now, state governments. As Product Manager for our Government Platform, you will lea…
Est. 250,000 USD
About Wonderschool Wonderschool builds software and systems that help businesses operate, grow, and generate revenue. We started in childcare and are expanding into adjacent verticals including healthcare, microschools,…
Est. 85,000 USD
Position Summary: Wonderschool is harnessing the power of technology to provide comprehensive support to child care providers operating out of their homes as well as in the government and non-profit sectors. Our products…
Est. 100,000 USD
Location: In-person, 5-6 days a week in our office in Rincon Hill, San Francisco (Travel Required) Company Overview: Wonderschool is harnessing the power of technology to provide comprehensive support to child care provi…
Est. 140,000 USD
About Wonderschool Wonderschool is on a mission to make high-quality early childhood education accessible to all. We empower child care providers with the tools and support they need to succeed while helping parents find…
Est. 120,000 USD
About WonderschoolWonderschool is the operating system for child care in America. State governments and large enterprises partner with us to run child care licensing, subsidy programs, and provider and family search on o…
Est. 80,000 USD
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…
Est. 450,000 USD
Wonderschool is harnessing the power of technology to provide comprehensive support to child care providers operating out of their homes as well as in the government and non-profit sectors. Our products enable child care…
Est. 140,000 USD
About Wonderschool Wonderschool builds software that helps small business owners earn more money. We started with childcare providers because it is a large, underserved market where technology can have an outsized impact…
Est. 150,000 USD
San Francisco, CA | Field + Hybrid OTE: $150K ($75K base / $75K variable) | Commission uncapped About Wonderschool Wonderschool builds the operating system for child care. We give providers, from in-home operators to lar…
Est. 140,000 USD
About 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…
Est. 110,000 USD
About Wonderschool Wonderschool is harnessing the power of technology to provide comprehensive support to childcare providers operating out of their homes as well as in the government and non-profit sectors. Our products…
Est. 140,000 USD
The OpportunityWonderschool is solving one of the most critical market problems in the U.S.: childcare access and affordability. We’re building an AI-powered platform that enables providers to operate financially sustain…
Est. 150,000 USD
About Wonderschool Wonderschool is harnessing the power of technology to support child care providers operating from their homes as well as in government and nonprofit sectors. Our products enable providers to build high…
Est. 250,000 USD
About Wonderschool Wonderschool builds software and systems that help businesses operate, grow, and generate revenue. We started in childcare, where we provide a platform that helps providers manage enrollment, operation…
Est. 140,000 USD
Most support teams react. We want to build one that prevents. Wonderschool serves government agencies, childcare providers, parents, and teachers across multiple products. This role exists to make sure every one of them…
Est. 137,500 USD
At Workwize, we’re helping IT teams to easily equip their remote and global teams with all necessary IT equipment. Our automated SaaS platform simplifies hardware deployment, management, and retrieval with fast, reliable…
Est. 85,000 GBP
About Wunderkind:Wunderkind is a performance marketing solution that uses AI and data to help brands acquire and retain customers through one-to-one, personalized messages across websites, email, text, and ads, guarantee…
Est. 140,000 USD
About Wonderschool Wonderschool's mission is to ensure every child has access to early education that helps them realize their full potential. We do this by helping providers - small business owners who run child care pr…
Est. 120,000 USD
About Wonderschool Wonderschool is a marketplace connecting families with high-quality early childhood education providers. We help educators launch and grow childcare programs, and we help parents find the right care fo…
Est. 144,000 USD
About Wonderschool Wonderschool’s mission is to ensure every child has access to early education that helps them realize their full potential. We do this by helping providers - small business owners who run in-home child…
Est. 80,000 EUR
About Workato Workato delivers enterprise infrastructure for the agentic era, redefining iPaaS and helping enterprises unify data, applications, processes, and AI into a single, governed platform. A leader in Enterprise…
About Workato Workato delivers enterprise infrastructure for the agentic era, redefining iPaaS and helping enterprises unify data, applications, processes, and AI into a single, governed platform. A leader in Enterprise…
Est. 85,000 USD
Position Summary The Operations Manager, New Initiatives manages the daily operations of Wonderschool’s Tri-Share and SubPool programs. This role ensures both programs have clear, reliable, and scalable processes that cr…
About impact.com impact.com is the world’s leading commerce partnership marketing platform, transforming the way businesses grow by enabling them to discover, manage, and scale partnerships across the entire customer jou…
Est. 115,000 USD
About Workato Workato delivers enterprise infrastructure for the agentic era, redefining iPaaS and helping enterprises unify data, applications, processes, and AI into a single, governed platform. A leader in Enterprise…
Est. 102,500 USD
About Us Planful is the pioneer of financial performance management cloud software. The Planful platform, which helps businesses drive peak financial performance, is used around the globe to streamline business-wide plan…
Est. 65,000 USD
About Us Planful is the pioneer of financial performance management cloud software. The Planful platform, which helps businesses drive peak financial performance, is used around the globe to streamline business-wide plan…