Head of Sales, Government
Description
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.
Skills
As published by greenhouse · 40 questions · 11 written answers
Basics
First Name, Last Name, Email, Phone, Resume/CV, Cover Letter
Short answers (21)
- LinkedIn Profile
- Website optional
- If based in San Francisco, can you work from our Rincon Hill office 5-6 days a week when you are not traveling?
- What level of travel can you commit to? We expect this role to require a lot of traveling.
- What is your current position?
- What is your current company?
- How many employees did the smallest company you worked at have while you were there? optional
- Smallest-company headcount — anything else to add? optional
- What was that company's name? optional
- How long did you work there, in months? optional
- Tenure length — anything else to add? optional
- Where did you attend and graduate from your undergraduate studies? optional
- What was your undergraduate major? optional
- Did you attend graduate school? If so, where? optional
- What was your graduate major? optional
- Fields worked in — anything else to add? optional
- Short tenure — anything else to add? optional
- Software sales — anything else to add? optional
- Which states have you worked with professionally through state governments or agencies? optional
- Travel ability — anything else to add? optional
- Products sold — anything else to add? optional
Pick from a list (8)
- Are you currently authorized to work in the United States?
- Do you now, or will you in the future, require sponsorship to work in the United States?
- What types of early childhood experience do you have?
- Which of these fields have you worked in?
- What was the main reason for a short tenure in a prior role?
- Has software you built or helped build generated more than $100 in sales?
- What’s your ability to travel for this role and for most jobs?
- What products have you sold? optional
Written answers (11)
- Tell us about your experience working with State Consultants to pass bills and secure appropriations?
- Tell us about your experience selling to State Governments.
- Tell us about your experience selling SaaS solutions.
- Tell us about your experience selling professional services.
- 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.
- What’s the largest deal you’ve closed?
- What’s the largest deal a team you’ve led has closed?
- Tell us about your experience managing long sales cycles. optional
- In 1–2 sentences, what makes you a fit for this role?
- What did you build or try to build, and what happened? optional
- Which agencies have you sold to? optional