Head of Sales, Government

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.