This listing pays about $217,500 a year. Across 37 open head of sales listings that state pay, the middle half runs $150,000 to $250,000 and the median is $200,000. That is inside the middle half of those listings, 9% above the median.

Listed pay is what employers advertise, not what people are paid.

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How AI is used in this kind of work

AI use among sales managers is little observed so far. Measured exposure for sales managers: 4% (little observed).

Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.

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About the job

About 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.

What You'll Own

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.

Who You Are

You have grown revenue selling SaaS, marketplace, or usage-based products to small businesses. You can explain your targets, results, and the decisions that improved performance.

You have hired, coached, and managed salespeople. You can point to people you helped become better sellers and the results they achieved.

You enjoy taking sales calls and closing deals. You earn the trust of business owners, ask good questions, explain products clearly, and move deals forward.

You take responsibility for results, make decisions with incomplete information, and follow through. You move comfortably between leading the team and doing the work yourself.

You have built or substantially improved a sales process in HubSpot, including routing, stages, sequences, workflows, forecasting, and reporting.

You work directly with your funnel data, identify where deals stall, and test changes that improve conversion and revenue.

You use AI in real sales workflows, can explain what it has improved, and are eager to help child care providers use it in their businesses.

You learn new products and customer needs quickly. Experience in child care, education, payments, or marketplaces is a plus.

Compensation and Location

We offer highly competitive compensation, uncapped earning potential, equity, and benefits.

This role is based in our San Francisco office Monday through Friday. Occasional weekend work may be required, either in the office or remotely.