Location: San Francisco (Rincon Hill)
Company Overview
Mission: Make high-quality early childhood education accessible to all by empowering childcare providers with tools and support while helping parents find quality learning environments.
What We're Building: A category-defining platform at the intersection of marketplace, SaaS, and public sector systems, increasingly powered by AI. Wonderschool helps providers manage operations, governments run large-scale childcare programs, and families find trusted care. Series B backed by a16z, Goldman Sachs, and First Round.
Company Culture: Small, fast-moving team that values ownership, rapid experimentation, and modern tools including AI and automation to increase leverage and impact.
Role Summary
Focus: Own the provider customer lifecycle funnel from first touch through expansion and cross-sell. You'll drive 3-5x revenue growth over 12-18 months through go-to-market execution, high-touch customer success, and enabled product-led growth. The vast majority of your work will be identifying and capturing cross-sell opportunities across our provider base. You'll combine hands-on operator skills, funnel management, and team leadership to unlock revenue by connecting providers with additional Wonderschool solutions.
Key Responsibilities
Own the Provider Funnel and Cross-Sell Growth
- Own end-to-end conversion and customer lifecycle funnel for non-paying providers becoming paying customers and identifying cross-sell expansion opportunities
- Develop deep understanding of provider pain points, business models, and decision-making frameworks
- Serve as the primary voice of the customer in product and business strategy discussions
- Identify and pursue expansion opportunities with existing customers across the full Wonderschool product suite
- Test and recommend pricing and packaging models to optimize conversion, expansion, and revenue
- Build measurement systems to track revenue impact of initiatives
- Set ambitious revenue targets and execute toward them with discipline
Enable Product-Led Growth Through Sales, Customer Success, and Account Management
- Support and activate product-led growth motions by building exceptional onboarding and success experiences that drive adoption and cross-sell
- Lead and manage provider success team executing customer success calls, account management, and quarterly business reviews
- Design and scale repeatable playbooks for provider onboarding, activation, and expansion across the product suite
- Develop coaching and enablement systems for small business consulting covering pricing, budgeting, operations, and growth strategies
- Build systems to identify at-risk providers and execute proactive retention strategies
- Establish clear accountability and performance metrics tied to revenue and customer outcomes
- Create a provider community and usage model around Wonderschool tools
Deploy AI Agents to Support Sales, Success, and Cross-Sell
- Partner with engineering to design and deploy AI agents that support provider engagement and drive cross-sell opportunities at scale:
- Sales agents for automated outreach, nurturing, and conversion support
- Onboarding agents for intake qualification, goal-setting, and tool enablement
- Account management and expansion agents for ongoing engagement, cross-sell identification, and retention
- Define agent personas, messaging frameworks, and success metrics
- Review, iterate on, and approve all agent communications
- Manage agent performance, measure impact on revenue and cross-sell conversion, and optimize continuously
- Develop playbooks for seamless agent-to-human handoffs in complex scenarios
Cross-Functional Leadership and Collaboration
- Collaborate closely with Product to inform roadmap based on provider feedback and revenue impact data
- Partner with Engineering to scope and execute agent builds and improvements
- Work with Sales on government sales dynamics, enterprise pricing, and procurement
- Influence company strategy on provider positioning, messaging, and go-to-market approach
- Champion provider voice internally; translate feedback into action
- Work in-person with cross-functional teams to enable real-time collaboration and decision-making
Required Qualifications
- 6+ years in customer success, account management, sales operations, or business development roles
- Proven ability to build and lead high-performing teams
- Demonstrated track record of driving revenue growth and new customer conversion in B2B environments
- Direct experience with enterprise or marketplace customer engagement
- Strong communication and influence skills, equally effective with customers and internal stakeholders
- Comfort with data and analytics; ability to extract insights and measure impact
- Experience operating in ambiguous, fast-paced startup environments
- 5 days/week in-office presence required to enable collaboration with cross-functional teams
Preferred Qualifications
- Marketplace or two-sided platform experience
- Government or public sector sales experience
- Experience building and scaling success teams during high growth
- Familiarity with regulated industries (healthcare, education, childcare)
- Early experience with AI tools, agents, or automation workflows
- Product thinking and ability to translate customer feedback into strategy
- Background in small business or entrepreneurship
- SaaS implementation or onboarding experience
- Track record of expansion revenue and cross-sell success
How You'll Work
Operating Model: Hands-on operator and strategic leader. You're expected to:
- Spend significant time directly with providers, visiting, conducting calls, and attending events to deeply understand their needs and identify expansion opportunities
- Use agentic tools (Claude Code, Hermes, OpenClaw) to automate workflows and measure impact
- Move fast and iterate based on feedback; bias toward action over perfect information
- Own your metrics end-to-end: from provider inputs to revenue outputs
- Partner with engineering and product on a daily basis to drive product-market fit
- Lead meetings with C-suite stakeholders; interface with government customers and partners
- Work in-person 5-6 days/week in our San Francisco office to enable real-time collaboration and drive cross-functional decision-making
What Success Looks Like (12-18 months):
- Active provider base generates 3-5x revenue growth from when you started
- Cross-sell playbooks are delivering measurable adoption of additional Wonderschool solutions
- Success playbooks are repeatable, measured, and becoming core to company operations
- High-performing team reporting to you with clear accountability to revenue and cross-sell metrics
Reporting Structure
This role reports into the executive team and sits within go-to-market and revenue operations, partnering closely with the product and engineering teams to execute GTM strategy and funnel management.
Compensation & Benefits
Base Salary: Competitive (commensurate with experience and market)
Equity: Meaningful equity package
Additional Compensation: Performance bonuses tied to revenue outcomes
Benefits Package:
- Health benefits: 100% coverage for employee premiums, 80% for dependents
- Dental and vision coverage
- 401(k) match
- Flexible PTO and paid holidays
- Mental wellness days
- Competitive parental leave (eligible after 6 months)
- WiFi, wellness stipends, and co-working space reimbursement
- Collaborative, mission-driven workplace environment
Application
Ready to help childcare providers grow and unlock value for Wonderschool? Apply now with your resume, a brief note on your most impactful revenue-driving accomplishment, and any questions you have about the role.
We review applications on a rolling basis and move quickly for strong candidates.