# Head of Implementation & Customer Success

**Company**: Wonderschool
**Location**: San Francisco
**Work arrangement**: hybrid
**Experience**: senior
**Job type**: full-time
**Salary**: $180,000 – $220,000
**Category**: Operations
**Industry**: Technology

**Apply**: https://job-boards.greenhouse.io/wonderschool/jobs/7658643003
**Canonical**: https://yubhub.co/jobs/job_e2d0a9bb-cf6

## Description

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.

## Skills

### Required
- Implementation
- Customer Success
- Program Management
- Operational Leadership
- Communication
- Executive Stakeholder Engagement

### Nice to have
- Government or Public Sector Customers
- Enterprise SaaS
- Professional Services
- Consulting
- Net Revenue Retention
- Regulated Industries