The posting, in Wonderschool's own words
archived Oct 27, 2026About Wonderschool
Wonderschool helps child care providers fill openings and run stronger businesses. Our marketplace connects providers with families, while our software supports enrollment, communication, payments, and daily operations. We sell SaaS products and usage-based marketplace solutions. AI is becoming part of how providers run their businesses. We are building tools that help them respond to families, manage enrollment, and make better business decisions.
The Role
We are looking for a Head of Sales to hire and manage our provider sales team and grow revenue from child care providers. You will convert inbound interest, build new pipeline, and help the team sell across our marketplace and SaaS solutions. You will be directly involved in the work. You will take provider calls, work alongside reps on important deals, and coach them through discovery, objections, follow-up, and closing. You will build the sales process in HubSpot and use AI to improve outbound, tracking, and team performance.
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Grow revenue
Own the provider sales team's revenue targets and results across SaaS and usage-based marketplace solutions. Improve conversion from first conversation through close and initial use. Build an outbound motion alongside our existing inbound demand. Grow revenue from existing providers by identifying opportunities to adopt additional Wonderschool products, in partnership with provider growth and customer success. Track the revenue generated by the providers the team signs, including revenue that depends on ongoing product usage. Use customer feedback and sales results to improve targeting, positioning, and the sales approach, and recommend changes to pricing and packaging.
Hire and lead the team
Hire, manage, and develop provider salespeople. Take calls yourself and join important or difficult deals. Review calls and coach reps on discovery, deal strategy, objections, follow-up, and closing. Set ambitious goals, develop your team's ability to meet them, and hold people accountable for results.
Build the sales system
Own lead routing, pipeline stages, sequences, workflows, follow-up, forecasting, and reporting in HubSpot. Create playbooks for selling both SaaS and usage-based marketplace solutions. Use funnel data to identify where deals stall, test improvements, and share a reliable forecast with leadership. Partner with provider growth and customer success so sales commitments lead to successful adoption and continued use.
Make AI useful
Use AI for prospect research, outbound outreach, call preparation, follow-up, and tracking. Measure whether AI improves qualified pipeline, conversion, and revenue. Help providers understand and use Wonderschool's AI tools to respond to families, manage enrollment, and run their businesses more effectively. Bring what you learn from provider conversations to product and engineering to improve the tools we build.
What Success Looks Like
Revenue from child care providers grows across SaaS and usage-based marketplace solutions. The team converts more inbound leads and creates a reliable source of qualified outbound opportunities. More reps consistently meet their revenue targets as coaching and sales playbooks improve. New hires become effective through clear onboarding, coaching, and performance expectations. HubSpot provides an accurate view of the pipeline and forecast. Providers activate the products they buy and continue using them, in partnership with provider growth and customer success.