Head of Sales, Providers

Wonderschool•San Francisco, CA

1d•Onsite

About The Position

Wonderschool is hiring a Head of Sales to lead its provider sales team and grow revenue from child care providers across SaaS products and usage-based marketplace solutions. The role combines team leadership with direct sales work: converting inbound interest, developing outbound pipeline, taking provider calls, joining important deals, and coaching representatives through the sales process. The Head of Sales will own the team’s revenue targets and results, improve conversion from first conversation through close and initial use, and identify opportunities to grow revenue from existing providers. The role also includes hiring and developing salespeople, building and improving sales processes in HubSpot, using funnel data to improve performance and forecasting, and partnering with provider growth and customer success to support product adoption and continued use. The position uses AI in prospect research, outreach, call preparation, follow-up, and tracking, with results measured through qualified pipeline, conversion, and revenue. The Head of Sales will also help providers use Wonderschool’s AI tools and share provider feedback with product and engineering. The role is based in Wonderschool’s San Francisco office Monday through Friday, with occasional weekend work potentially required. Compensation includes highly competitive compensation, uncapped earning potential, equity, and benefits.

Requirements

Experience growing revenue by selling SaaS, marketplace, or usage-based products to small businesses, with the ability to explain targets, results, and performance-improving decisions.
Experience hiring, coaching, and managing salespeople, with examples of helping sellers improve and achieve results.
Enjoys taking sales calls and closing deals; can build trust with business owners, ask effective questions, explain products clearly, and move deals forward.
Takes responsibility for results, makes decisions with incomplete information, follows through, and can lead a team while also doing the work directly.
Experience building or substantially improving a sales process in HubSpot, including routing, stages, sequences, workflows, forecasting, and reporting.
Ability to work directly with funnel data, identify where deals stall, and test changes that improve conversion and revenue.
Uses AI in real sales workflows, can explain its impact, and is eager to help child care providers use AI in their businesses.
Ability to learn new products and customer needs quickly.

Nice To Haves

Experience in child care, education, payments, or marketplaces.

Responsibilities

Own provider sales team revenue targets and results across SaaS and usage-based marketplace solutions.
Improve conversion from first conversation through close and initial product use.
Build an outbound sales motion alongside existing inbound demand.
Identify opportunities to grow revenue from existing providers by encouraging adoption of additional products, in partnership with provider growth and customer success.
Track revenue generated by signed providers, including revenue dependent on ongoing product usage.
Use customer feedback and sales results to improve targeting, positioning, and sales approach, and recommend pricing and packaging changes.
Hire, manage, and develop provider salespeople.
Take provider calls and participate in important or difficult deals.
Review calls and coach representatives on discovery, deal strategy, objections, follow-up, and closing.
Set ambitious goals, develop the team’s ability to meet them, and hold people accountable for results.
Own HubSpot lead routing, pipeline stages, sequences, workflows, follow-up, forecasting, and reporting.
Create playbooks for selling SaaS and usage-based marketplace solutions.
Use funnel data to identify stalled deals, test improvements, and provide leadership with a reliable forecast.
Partner with provider growth and customer success to support successful adoption and continued product use.
Use AI for prospect research, outbound outreach, call preparation, follow-up, and tracking, and measure its impact on pipeline, conversion, and revenue.
Help providers understand and use Wonderschool’s AI tools to respond to families, manage enrollment, and run their businesses.
Share insights from provider conversations with product and engineering to improve the tools being built.