Principal Engineer, AI

Responsibilities

• In this role, you will:
• Own outcomes end-to-end. Take responsibility for turning high-leverage opportunities into shipped, adopted capabilities with clear measurement, iteration loops, and sustained improvement-not one-time launches.
• Define the AI technical direction for your organization. Translate customer problems into a practical strategy, reference architectures, and a roadmap that multiple teams can execute against, with minimal guidance.
• Drive build-versus-buy decisions. Recommend when to partner on models and tooling versus when to build differentiated capabilities (data flywheels, evaluation systems, workflow-specific intelligence), backed by evidence from fast, hands-on spikes.
• Lead by implementation. Rapidly prototype and ship reference implementations to prove feasibility, de-risk decisions, and raise your teams' expectation for speed and ambition.
• Help build the paved highway. Contribute shared foundations-evaluation harnesses, retrieval and context patterns, safety guardrails, observability, and developer experience-so teams can ship reliable AI features repeatedly and independently.
• Raise the bar across your organization. Mentor senior and staff engineers, lead design reviews for your teams, help establish standards for quality and safety, and align stakeholders to drive adoption.
• What You've Done
• We are open to a variety of backgrounds, but strong candidates usually bring:
• Foundational AI Depth: You possess deep intuition for why models fail, gained from experience that predates the LLM boom. You have likely worked with model training, fine-tuning, or classical NLP/ML, giving you the grounding to make sound architectural decisions.
• 8+ Years of Engi

Requirements

• 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 strategy and deep implementation. You set the technical direction for your organization, 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 their 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.

Benefits

Additional Information

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 , 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 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.

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