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Sales leadership

Head of Sales, Government

Wonderschool logoWonderschoolRemote, any countryListed 1y+ ago
Apply on Wonderschool (shows the role here)Before you apply: what we know about Wonderschool

The posting

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 providers to create high-quality environments and meet the demands of their business, while also helping parents in need of childcare solutions through the creation of an accessible marketplace.

We are seeking a Head of State Government Sales who is a first-principles thinker with a proven track record in government sales. San Francisco is preferred, but we will consider exceptional candidates anywhere in the US. This role reports directly to the CEO.

Wonderschool already has active partnerships across 15 states and a very rich pipeline. This is not a build-from-scratch role - you’re coming in to scale what’s already working.

This is not a 9-to-5 job. It requires a significant amount of travel - you will attend events throughout the country, work alongside marketing to generate leads and attract the full funnel, and personally carry a bag while building and leading a sales team.

Compensation

$450,000 OTE + equity

What You’ll Do

  • Take ownership of a well-defined, proven sales playbook and scale it across states, cities, and counties
  • Run meetings, develop pipeline, and own go-to-market strategy for government sales
  • Sell - this is a player-coach role; a significant portion of your time will be in front of customers closing deals
  • Hire, coach, and develop a high-performing sales team
  • Partner with marketing to drive event presence, lead generation, and top-of-funnel pipeline
  • Leverage AI tools to accelerate outreach, communications, and pipeline management
  • Build and maintain strong relationships with key government stakeholders - agencies, elected officials, regulators, and associations
  • Develop data-driven forecasts and report pipeline health and learnings to leadership
  • Refine deal desk, sales qualification, and process as we grow

What We’re Looking For

  • A first-principles thinker who doesn’t just follow playbooks - you understand why they work and know how to adapt
  • Proven government sales background with experience closing SaaS-based contracts with state, city, or county agencies
  • Demonstrated track record closing $1M–$15M+ ARR deals with government entities
  • Deep familiarity with government procurement processes
  • Experienced team leader and recruiter who can attract and develop great salespeople
  • Highly data-driven with a bias toward accountability and measurable outcomes
  • Comfortable with significant travel and an events-heavy calendar
  • Ready to work with and maximize AI-powered tools for outreach and communications
  • Experienced enough to operate independently, but hungry enough to still love selling

You’ll have strong support from the CEO, a clear playbook, and existing momentum across 15 states. The opportunity to build something meaningful is real. We want someone experienced, energized, and ready to scale.

This is a full-time role, 5-6 days a week, with significant travel and an events-heavy calendar.

Where you can sell from

Fully remote, and open to sellers in any country.

Taken from Wonderschool's own posting, last seen live on 3 Nov 2026.

Apply on Wonderschool (shows the role here)

The application

Your details, CV and LinkedIn, then 38 questions (11 written).

Have readyCVLinkedInCover letter (optional)Website (optional)
  1. 1.
    Tell us about your experience working with State Consultants to pass bills and secure appropriations?Written answer
  2. 2.
    Tell us about your experience selling to State Governments.Written answer
  3. 3.
    Tell us about your experience selling SaaS solutions.Written answer
  4. 4.
    Tell us about your experience selling professional services.Written answer
  5. 5.
    Tell us about your experience working through the Legislative cycle to win deals. If no experience - tell us about the complexity of your Enterprise sales.Written answer
  6. 6.
    What’s the largest deal you’ve closed?Written answer
  7. 7.
    What’s the largest deal a team you’ve led has closed?Written answer
  8. 8.
    Tell us about your experience managing long sales cycles.Written answer · optional
  9. 9.
    If based in San Francisco, can you work from our Rincon Hill office 5-6 days a week when you are not traveling?Short answer
  10. 10.
    What level of travel can you commit to? We expect this role to require a lot of traveling.Short answer
  11. 11.
    What is your current position?Short answer
  12. 12.
    What is your current company?Short answer
  13. 13.
    Are you currently authorized to work in the United States?Yes or no
  14. 14.
    Do you now, or will you in the future, require sponsorship to work in the United States?Yes or no
  15. 15.
    What types of early childhood experience do you have?Pick any (7 options)
  16. 16.
    How many employees did the smallest company you worked at have while you were there?Short answer · optional
  17. 17.
    Smallest-company headcount - anything else to add?Short answer · optional
  18. 18.
    What was that company's name?Short answer · optional
  19. 19.
    How long did you work there, in months?Short answer · optional
  20. 20.
    Tenure length - anything else to add?Short answer · optional
  21. 21.
    In 1-2 sentences, what makes you a fit for this role?Written answer
  22. 22.
    Where did you attend and graduate from your undergraduate studies?Short answer · optional
  23. 23.
    What was your undergraduate major?Short answer · optional
  24. 24.
    Did you attend graduate school? If so, where?Short answer · optional
  25. 25.
    What was your graduate major?Short answer · optional
  26. 26.
    Which of these fields have you worked in?Pick any: Private equity · Investment banking · Consulting · None
  27. 27.
    Fields worked in - anything else to add?Short answer · optional
  28. 28.
    What was the main reason for a short tenure in a prior role?Pick one: Reduction in force · Fit · Other · N/A
  29. 29.
    Short tenure - anything else to add?Short answer · optional
  30. 30.
    What did you build or try to build, and what happened?Written answer · optional
  31. 31.
    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.
  32. 32.
    Software sales - anything else to add?Short answer · optional
  33. 33.
    Which states have you worked with professionally through state governments or agencies?Short answer · optional
  34. 34.
    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
  35. 35.
    Travel ability - anything else to add?Short answer · optional
  36. 36.
    Which agencies have you sold to?Written answer · optional
  37. 37.
    What products have you sold?Pick any: Software · Services · Curriculum · Other · optional
  38. 38.
    Products sold - anything else to add?Short 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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