Senior Principal Engineer, Brightwheel

• 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
• 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 mathematical grounding to make high-stakes architectural decisions
• 10+ Years of Engineering Excellence: You have end-to-end ownership of large, business-critical systems. You have moved beyond solving defined problems to identifying and solving "intrinsically hard" challenges where the solution—and sometimes the problem itself—was initially unknown
• Strategic Architecture: Experience formulating technical strategy at the organization or department level. You have successfully designed systems that required execution across multiple teams or organizations
• The "Player-Coach" Standard: A track record of mentoring Staff and Principal engineers. You don't just review code; you raise the bar for hiring, design, and operational excellence across the entire engineering department
• Production AI at Scale: A proven track record of shipping AI-powered products to production. You understand the "last mile" of AI—evaluation, monitoring, and safety—and have built the tools that allow teams to sleep soundly at night

Desirable

• 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
• 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, evaluation systems, workflow-specific intelligence) that create durable advantage
• Lead by implementation. Rapidly prototype and ship reference implementations to prove feasibility, de-risk decisions, and raise the organization’s expectation for speed and ambition
• Create the paved highway. Build 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 Engineering and Product. Mentor senior engineers, lead design reviews, establish standards for quality and safety, and align stakeholders across teams to drive adoption
• We work with:
• Backend: Ruby on Rails, Sidekiq
• Data: PostgreSQL on Amazon RDS, Redis, and event and analytics pipelines
• Frontend: React with TypeScript and Emotion
• Mobile: Native iOS (Swift) and Android (Kotlin with Jetpack Compose)
• Cloud & Infrastructure: Docker, Kubernetes on Amazon EKS, GitHub Actions and FluxCD for CI/CD, and AWS services such as S3, CloudFront, CloudWatch, and SNS
• AI & Automation: AWS Bedrock and other hosted large language models, vector search, orchestration and agent frameworks, and modern AI coding tools like Cursor