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.
Requirements
Who You Are You are a Senior Principal Engineer who is both AI-native and relentlessly product-minded.
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 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.
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.
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.
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.
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
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. Nice-to-haves: -
Experience earlier in your career with model training, fine-tuning, classical machine learning, or natural language processing—enough to have intuition for why models fail and how data and evaluation shape outcomes. - A portfolio of real work (open-source, demos, writing, talks, or shipped side projects) that shows taste, velocity, and how you think about applied AI systems end-to-end. -
- Formal training in computer science (4-year CS degree or equivalent depth in core CS topics).
Technology 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
Experience
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.
Benefits
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.
Contact
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.
We embody our Leadership Principles https://mybrightwheel.com/about/ in our work and culture.
All legitimate communications come from @mybrightwheel.com http://mybrightwheel.com addresses, and we never ask for payment or sensitive personal data as part of our hiring process.
If you suspect fraudulent contact, reach out to security@mybrightwheel.com.
Additional details
Brightwheel is the largest, fastest growing, and most loved platform in early ed, trusted by millions of educators and families every day.
Our Team Our team is passionate, talented, and customer-focused.
We are a distributed team with remote employees across every US time zone, as well as select offices in the US and internationally.
You turn ambiguous, cross-functional opportunities into clear technical direction,and then you prove the path by building.
You will succeed in this role if you are: - Driven by outcomes.
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