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 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.