# Head of Implementation & Customer Success

**Company:** [Wonderschool](https://hotfix.jobs/companies/wonderschool)
**Location:** San Francisco, CA
**Role:** Customer Success
**Salary:** $180k – $220k/yr
**Experience:** 8+ years
**Skills:** SaaS, Customer Success, Program Management, Implementation, Professional Services, Net Revenue Retention, Nrr, Customer Health Monitoring, Data Migration, System Integrations, Stakeholder Management
**Posted:** 2026-04-27

> Leads post-sale lifecycle for government and enterprise customers, owning complex implementations, building scalable customer success playbooks and teams, and driving adoption, retention, and expansion. Requires 8-12+ years in B2B SaaS post-sales with program management expertise.

## Job Description

## 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

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