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 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.