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.