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.