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 packageAdditional 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.