Provider Growth & AI Agent Operations Lead San Francisco

Location: San Francisco (Rincon Hill)

About the Role

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.

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

Requirements

• 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.

Benefits

• 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