[Remote] Principal Engineer, AI

Note: The job is a remote job and is open to candidates in USA. Brightwheel is the largest and fastest growing platform in early education, committed to improving childhood outcomes through technology. They are seeking a Principal Engineer, AI who will drive the technical direction for AI-powered capabilities that enhance business outcomes for schools, educators, and families.ResponsibilitiesOwn 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 launchesDefine 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 guidanceDrive 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 spikesLead by implementation. Rapidly prototype and ship reference implementations to prove feasibility, de-risk decisions, and raise your teams' expectation for speed and ambitionHelp 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 independentlyRaise 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 adoptionSkillsDeep intuition for why models fail, gained from experience that predates the LLM boomExperience with model training, fine-tuning, or classical NLP/ML8+ Years of Engineering ExcellenceEnd-to-end ownership of large, business-critical systemsExperience launching large-scale and/or highly complex softwareArchitectural Strategy experience at the organization levelExperience designing systems that required execution across multiple teamsTrack record of mentoring senior and staff engineersExperience improving skills, knowledge, and ability to get things doneProven track record of shipping AI-powered products to productionUnderstanding of evaluation, monitoring, and safety in AIExperience building tools that allow teams to sleep soundly at nightExperience earlier in your career with model training, fine-tuning, classical machine learning, or natural language processingA portfolio of real work (open-source, demos, writing, talks, or shipped side projects)Experience building shared internal platforms or frameworksFormal training in computer science (4-year CS degree or equivalent depth in core CS topics)A strong bar for operational excellence: secure-by-default design, performance and cost discipline, testability, incident readinessCompany OverviewBrightwheel is a software platform for preschools and childcare providers. It was founded in 2014, and is headquartered in San Francisco, California, USA, with a workforce of 201-500 employees. Its website is http://www.mybrightwheel.com.Company H1B Sponsorshipbrightwheel has a track record of offering H1B sponsorships, with 4 in 2025, 3 in 2024, 2 in 2023, 1 in 2022, 4 in 2021, 1 in 2020. Please note that this does not guarantee sponsorship for this specific role.