Wonderschool
Provider Growth & AI Agent Operations Lead 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
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.