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Customer success

Head of Implementation & Customer Success

Wonderschool logoWonderschool$180,000–$220,000/yrSan FranciscoListed 7mo ago
Apply on Wonderschool (shows the role here)Before you apply: what we know about Wonderschool

Taken at the midpoint of its range, $200,000/yr, this role pays more than the middle Customer Success opening on the board today ($143k/yr); the usual band for that kind of seat is $113k–$252k/yr.

The posting

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.

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 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.

Taken from Wonderschool's own posting, last seen live on 2 Nov 2026.

Apply on Wonderschool (shows the role here)

The application

Your details and CV, then 29 questions (3 written).

Have readyCVCover letter (optional)LinkedIn (optional)Website (optional)
  1. 1.
    Are you currently authorized to work in the US?Yes or no
  2. 2.
    Will you require any visa sponsorship to be legally authorized to work in the US?Yes or no
  3. 3.
    What types of early childhood experience do you have?Pick any (7 options)
  4. 4.
    How many employees did the smallest company you worked at have while you were there?Short answer · optional
  5. 5.
    Smallest-company headcount - anything else to add?Short answer · optional
  6. 6.
    What was that company's name?Short answer · optional
  7. 7.
    How long did you work there, in months?Short answer · optional
  8. 8.
    Tenure length - anything else to add?Short answer · optional
  9. 9.
    In 1-2 sentences, what makes you a fit for this role?Written answer
  10. 10.
    Where did you attend and graduate from your undergraduate studies?Short answer · optional
  11. 11.
    What was your undergraduate major?Short answer · optional
  12. 12.
    Did you attend graduate school? If so, where?Short answer · optional
  13. 13.
    What was your graduate major?Short answer · optional
  14. 14.
    Which of these fields have you worked in?Pick any: Private equity · Investment banking · Consulting · None
  15. 15.
    Fields worked in - anything else to add?Short answer · optional
  16. 16.
    What was the main reason for a short tenure in a prior role?Pick one: Reduction in force · Fit · Other · N/A
  17. 17.
    Short tenure - anything else to add?Short answer · optional
  18. 18.
    What did you build or try to build, and what happened?Written answer · optional
  19. 19.
    Has software you built or helped build generated more than $100 in sales?Pick one: Yes · No · Not sure · Have not built or helped build software.
  20. 20.
    Software sales - anything else to add?Short answer · optional
  21. 21.
    What is your current location?Pick one (11 options)
  22. 22.
    Can you work Monday-Friday in our San Francisco office, often on Saturdays, and be available Sundays when needed for child care customer events? This is a highly collaborative, in-person role.Pick one: Yes · Under certain circumstances · I'd like to learn more before deciding · No
  23. 23.
    SF office schedule - anything else to add?Short answer · optional
  24. 24.
    Can you generally work 9am-7pm, including occasional late customer meetings or deadlines and work lunches or dinners? Wonderschool covers travel home when you work late.Pick one: Yes · Under certain circumstances · I'd like to learn more before deciding · No
  25. 25.
    Work hours - anything else to add?Short answer · optional
  26. 26.
    Which states have you worked with professionally through state governments or agencies?Short answer · optional
  27. 27.
    What’s your ability to travel for this role and for most jobs?Pick one: 0% · 5-20% · 20-50% · more than 50% · as much as needed
  28. 28.
    Travel ability - anything else to add?Short answer · optional
  29. 29.
    Describe a complex customer implementation you led, how you drove adoption, and the outcome.Written answer · optional

From Wonderschool's apply page, checked 1 Nov 2026.

About Wonderschool

Sells enrollment, billing and subsidy software, a family-to-provider marketplace and payment tools to child care operators, and child care systems to state and local governments.

Pay schedule: Base salary plus commission (uncapped on the provider side) and stock options or equity, health premiums covered up to 100% for employees and 80% for dependents, and 5 to 6 day weeks, with government sellers on the road about 40% of the time.

Wonderschool's sales postings, in full Live feed of Wonderschool openings The Wonderschool company page

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