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Head of Trust & Safety

MagicSchool AI - Remote - Remote - posted 2026-10-15

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MagicSchool is a generative AI platform for teachers with over 7 million users globally. You will lead the Trust & Safety function as a Director-level role, owning all aspects of AI safety, responsible deployment, and incident response for a product serving educators and students worldwide. Key Responsibilities: - Own the safety of AI output to teachers and students, including policy development, model-level guardrails, evaluations, red-teaming, and incident response. - Establish and maintain trust posture with school districts through safety documentation, RFP responses, and alignment with state AI-in-education guidance. - Integrate safety evaluations and monitoring into product infrastructure, ensuring each new tool includes safety acceptance criteria during scoping rather than at launch. - Manage student-facing safety specifically: age-appropriate content, self-harm and crisis handling, and escalation paths to educators. - Run the safety incident process end-to-end and own the postmortem feedback loop into product and engineering teams. - Partner with Legal on COPPA, FERPA, state privacy laws, and emerging AI regulation, with T&S owning operational reality and Legal owning legal position. - Build and lead a small team (1–3 initially), scaling through 2027. You will work with a multi-provider LLM stack (OpenAI, Anthropic, Google via GCP Vertex), custom classifiers, Datadog for observability, and incident management tools (Linear, Slack, Notion). The product is built on TypeScript/Next.js on Vercel with Supabase PostgreSQL backend. REQUIREMENTS: Must Haves: - Proven ownership of trust & safety or responsible AI for a consumer or youth-facing product at scale, with real incidents, real policy decisions, and regulator interactions. - Hands-on expertise with LLM safety: evals, classifiers, prompt/system-level guardrails, red-teaming. Ability to read eval results and determine what to change. - Track record of making safety a velocity enabler, not friction—building guardrails as infrastructure so teams ship faster with confidence. - Ability to make judgment calls under ambiguity and own them publicly to districts and executive team. - Strong writing skills: safety documentation, district-facing explainers, incident communications. - Hypothesis-first mindset; escalates one-way doors quickly rather than delaying decisions. Nice to Haves: - K-12 or youth-platform experience (GoGuardian, Securly, Roblox, Discord, YouTube Kids, Epic Games). - Familiarity with state AI-in-education frameworks and district procurement questionnaires. - Prior work with child-safety NGOs or standards bodies (Common Sense Media, NCMEC, Thorn, ISTE). - Data/ML fluency to partner directly with engineering on classifiers and eval pipelines. - Comfort being the external face of safety at conferences, with press, and in front of district boards.

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