Head of AI Agent Systems

About Wonderschool

Wonderschool builds software and systems that help businesses operate, grow, and generate revenue.

We started in childcare, where we provide a platform that helps providers manage enrollment, operations, compliance, and payments. We also partner with governments to run large-scale childcare programs.

We are a Series B company backed by Andreessen Horowitz, Goldman Sachs, Long Journey Ventures, and First Round Capital. The business is cash flow positive and expanding that position.

We are building a unified platform that combines marketplace, SaaS, and government infrastructure. We are expanding into adjacent verticals over time, including healthcare, microschools, and other service-based businesses.

A core part of our strategy is using AI to automate how work gets done across the company. This includes product development, operations, customer support, and go-to-market. We are also building systems to improve compliance, oversight, and fraud detection, particularly in government-funded programs.

We have already deployed a multi-agent system using OpenClaw and our internal Claude Code system. These agents operate across product, engineering, design, data, and operations. Parts of the system work today. Much of it is inconsistent, hard to measure, and not reliable enough for production use.

This role is responsible for fixing that and turning it into a system that drives revenue.

Position Summary

The Head of AI Agent Systems owns the design, performance, and evolution of Wonderschool’s multi-agent system.

This role is responsible for turning a partially working agent system into a production-grade platform that directly drives revenue by improving how we acquire customers, onboard them, operate their businesses, and iterate on product.

This is a hands-on role. You will work directly in the codebase, agent system, and infrastructure while leading a small team of engineers. You will be responsible for making the system work in practice and tying it to business outcomes.

This role reports directly to the CEO.

Responsibilities

Drive Revenue Through Agent Systems

Design and deploy agent-driven workflows that directly impact revenue generation

Improve conversion, onboarding speed, and provider revenue through automation

Partner with product and go-to-market to identify high-leverage revenue opportunities and implement them through agent systems

Use agents to accelerate experimentation on pricing, enrollment, and growth features

Tie agent performance to business outcomes such as revenue growth, conversion rates, and usage

Own Agent System Architecture and Performance

Own the architecture of the multi-agent system including OpenClaw, Claude Code, GBrain, and internal tooling

Improve agent output quality so outputs are usable without heavy human correction

Identify and fix system-level issues including poor outputs, coordination failures, memory loss, and context limitations

Design evaluation systems to measure success rates, failure modes, and reliability

Build a Reliable Multi-Agent Execution System

Redesign agent workflows so core processes execute reliably end-to-end

Ensure product development workflows from requirements through deploy can run through agents

Improve agent-to-agent coordination so tasks are completed without manual intervention

Introduce validation layers, retry logic, and clear ownership across workflows

Drive Adoption Across the Company

Enable engineering, product, design, go-to-market, and operations teams to use agents in their daily workflows

Define and enforce standards for how work is done using agents

Reduce reliance on manual processes by shifting execution to agent systems

Ensure systems are usable by non-engineers

Build Measurement and Feedback Loops

Implement system-wide reporting on agent performance

Track success rates, failure types, task completion, and human intervention

Use this data to continuously improve system performance

Create a system that improves over time rather than degrading

Lead and Scale the Team

Lead a small team of 2-3 engineers including DevOps

Hire and develop engineers who can build and operate agent systems

Maintain a high performance bar and clear accountability

Balance hands-on work with team leadership

Drive Business Impact

Increase provider revenue and platform usage through better systems

Improve speed of shipping features tied to revenue and growth

Automate workflows that reduce cost and increase margins

Support fraud detection and compliance systems that protect revenue and improve program integrity

What Success Looks Like (6-12 months)

Agents produce high-quality outputs with minimal human correction

All agents are tracked and measurable across success rate, failure modes, and usage

Teams across engineering, product, and operations use agents in daily workflows

Core workflows run reliably through agent systems

Agent systems are directly tied to measurable revenue outcomes including increased conversion, faster onboarding, and higher revenue per provider

Required Qualifications

Strong engineering background with experience building and shipping production systems

Experience working with AI systems, LLMs, or automation in a real environment

Experience debugging complex systems and improving reliability

Ability to work directly in code and system architecture

Experience building internal tools or developer systems is strongly preferred

Ability to operate in a fast-paced, high-ownership environment

Preferred Qualifications

Experience building or working with multi-agent systems

Experience with workflow automation or internal platforms

Experience working with regulated systems or compliance-heavy environments

Background as a founder or early engineer at a startup

What We Are Looking For

Someone who builds systems that work, not just prototypes

Someone who can take a messy system and make it reliable

Someone who connects technical systems to business outcomes and cares about revenue

Someone who moves quickly and focuses on outcomes

Someone who is comfortable working directly with leadership and making decisions

What This Role Is Not

Not a traditional Head of Engineering role

Not focused on managing large teams

Not a research or experimentation role

Location

This role is in-person, 5-6 days a week in our office in Rincon Hill, San Francisco.