Provider Growth & AI Agent Operations Lead

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 - 5-6 days a week in the Rincon Hill office 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.