Sr. Principal Engineer, AI

Sr. Principal Engineer, AI Our Mission and Opportunity Early education is one of the most important determinants of childhood outcomes, a critical support for working families, and a $175B market that remains underserved by modern technology. Brightwheel is the largest, fastest growing, and most loved platform in early ed, trusted by millions of educators and families every day. We are a three-time Cloud 100 company https://www.forbes.com/lists/cloud100/a, backed by top investors including Addition, Bessemer, Emerson Collective, Lowercase Capital, Notable Capital, and Mark Cuban. Our Team Our team is passionate, talented, and customer-focused. We embody our Leadership Principles https://mybrightwheel.com/about/ in our work and culture. We are a distributed team with remote employees across every US time zone, as well as select offices in the US and internationally. Who You Are You are a Senior Principal Engineer who is both AI-native and relentlessly product-minded. You turn ambiguous, cross-functional opportunities into clear technical direction,and then you prove the path by building. You care about the flagship experiences you ship, and you obsess over the shared “paved highway” that makes it easy for many teams to ship safe, reliable AI over and over again. You will succeed in this role if you are: - Driven by outcomes. You care about helping centers stay full, save hours every week, and serve families better, not shipping “an AI feature” for its own sake. - The strategic architect and prolific builder. You bridge executive strategy and deep implementation. You set the technical north star, then you get hands-on to deliver reference implementations that teams can adopt with confidence. - Decisive on build vs. buy. You have sharp judgment on when to leverage off-the-shelf models and platforms versus when to invest in proprietary infrastructure, fine-tuning, data flywheels, or evaluation systems to create durable advantage. - Velocity as a strategy (“show, don’t tell”). You move with the hunger of a founding engineer: you prototype boldly, de-risk quickly, and use working systems, not slides, to align teams and raise the organization’s ambition and pace. - A force multiplier with a platform mindset. You build the paved road: evaluation harnesses, retrieval and context patterns, safety guardrails, observability, and developer experience that let product and engineering teams ship AI safely and autonomously. - Deep on fundamentals, modern in practice. You understand why models fail (data, evaluation, human feedback, reliability), and you aggressively use modern AI-native tooling to iterate faster without sacrificing rigor. - Security- and trust-minded. You treat sensitive school, educator, and family data with care, design for least-privilege access, and build systems that are explainable, monitorable, and resilient. - Mission-aligned. The idea of using AI to expand childcare capacity and improve early education outcomes, at meaningful scale, genuinely motivates you. What You’ll Do You will make brightwheel measurably more valuable to schools, centers, educators, and families by delivering AI-powered capabilities that move company-level outcomes—for example retention, enrollment conversion, payment success, operational efficiency, and support burden. This is not a research role or a “build cool demos” role; success is defined by impact in production. In this role, you will: - Own outcomes end-to-end. Take responsibility for turning the biggest opportunities into shipped, adopted capabilities with clear measurement, iteration loops, and sustained improvement—not one-time launches. - Define the AI technical direction. Translate customer problems into a practical strategy, reference architectures, and a roadmap that multiple product teams can execute against. - Make build-versus-buy decisions. Choose when to partner on models and tooling versus when to build differentiated capabilities (data flywheels, evalua ... (truncated, view full listing at source)