Director, AI Engineering

Brightwheel is the largest and fastest growing platform in early education, trusted by millions of educators and families. The Director of AI Engineering will lead engineering teams to deliver AI-powered product capabilities, drive operational efficiency, and enhance customer value through innovative AI solutions.

Responsibilities:

• Lead engineering teams that deliver AI-powered product and platform capabilities with clear impact. Reduce administrative toil, improve family responsiveness, streamline enrollment, and surface better insights for operators
• Build software that not only records information, but also recommends next steps, completes routine work, and automates meaningful parts of our customers’ day-to-day operations
• Use AI agents, automation, and modern tooling to improve how teams build, test, ship, and support software, increasing velocity and freeing up more capacity for high-value work
• Operate an AI hybrid engineering workforce in which engineers and agents work together effectively, with the tooling, guardrails, governance, evaluation, and observability required
• Apply the same AI-native mindset to internal functions like customer support and onboarding, helping the company become faster, more responsive, and more efficient as it scales
• Drive continuous improvements in quality, reliability, and security by using agentic workflows to catch issues earlier, reduce operational burden, and improve the product every week
• Hire and scale exceptional AI-native engineering talent, building a lean, high-performing organization with high standards, strong ownership, and a bias for action
• Make strong build-versus-buy, architecture, and platform decisions that balance short-term speed with long-term leverage and differentiation

Requirements:

• A strong computer science foundation. You have a 4-year computer science degree or equivalent depth in core computer science topics, with the technical grounding to reason well across systems, abstractions, and tradeoffs
• A record of shipping battle-tested products at scale. You have helped deliver customer-facing software from pixels to metal, in either consumer or enterprise software. You have seen what it takes to make products succeed in real production environments with real customers and business stakes
• Applied AI experience in production. You have used AI, automation, or machine learning in high-stakes environments, whether in customer-facing products, internal systems, or engineering workflows. You understand what it takes to make these systems useful, reliable, safe, and cost-effective
• Experience leading through leaders. You have managed managers and senior engineers, building teams that consistently delivered meaningful product or platform outcomes in demanding, fast-paced environments
• Product taste and judgment. You operate without needing a product manager crutch. You are excited by the challenge of defining the right thing to build, not just building it right. In the age of AI, you use your product intuition to bridge the gap between technical possibility and customer value
• High-stakes communication and influence. You are equally comfortable in the boardroom and the IDE. You can persuade a C-suite audience on high-stakes strategic bets while maintaining the deep technical respect of the engineers who are building the systems
• A proven talent magnet. You have a track record of building or turning around teams in highly competitive hiring arenas. You have successfully attracted and retained top talent
• You are a T-shaped leader, deeply expert in at least one domain but capable of becoming proficient just-in-time across science, data, security, infra, and UX. You use AI to multiply your learning speed, allowing you to handle the full breadth of a modern engineering organization
• Hands-on fluency with AI-native development. You do not just manage; you build. You have used AI assistants and agents to materially improve your own speed and quality, and you have a clear perspective on how to help an entire organization adopt these workflows effectively