Head of Trust & Safety - MagicSchool

Who We Are

MagicSchool is the premier generative AI platform for teachers. We're just over 2 years old, and more than 7 million teachers from all over the world have joined our platform. Join a top team at a fast-growing company working toward real social impact.

Responsibilities

• Own the safety of AI output to teachers and students: policy, model-level guardrails, evals, red-teaming, and incident response.
• Own the trust posture with districts: safety documentation, RFP and school-board responses, and alignment with state AI-in-education guidance.
• Develop safety evaluations and monitoring as integral components of product infrastructure; ensure that each new tool includes safety acceptance criteria established during the scoping phase, rather than at launch.
• Own 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 loop back into product and engineering.
• Partner with Legal on COPPA, FERPA, state privacy laws, and emerging AI regulation. Trust & Safety owns the operational reality; Legal owns the legal position.
• Build and lead a small team (1–3 to start), scaling the function through 2027.

Qualifications & Skills

Must Haves

• Has owned trust & safety or responsible AI for a consumer or youth-facing product at scale: real incidents, real policy decisions, real regulators.
• Hands-on with LLM safety: evals, classifiers, prompt/system-level guardrails, red-teaming. Can read an eval result and determine necessary adjustments.
• Has made safety a velocity enabler, not friction — builds guardrails as infrastructure so teams ship faster with confidence.
• Makes judgment calls under ambiguity and owns them publicly, to districts and to the executive team.
• Strong writer: safety documentation, district-facing explainers, incident communications.
• Operates hypothesis-first and escalates one-way doors quickly rather than delaying action.

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.
• Comfortable being the external face of safety at conferences, with press, and in front of district boards.

Tech Stack

• LLM Layer: Multi-provider (OpenAI, Anthropic, Google via GCP Vertex); moderation APIs and custom classifiers.
• Safety Tooling: Eval and red-team tooling (to be built out); Datadog for output observability and alerting.
• Product Stack Context: TypeScript, Next.js on Vercel, Supabase (PostgreSQL) backend.
• Incident & Knowledge Tooling: Linear, Slack workflows, Notion.

Benefits & Perks

• Unlimited time off (PTO) to manage work-life balance.
• Employer-paid health insurance plans, with low-premium dental and vision coverage.
• Generous stock options vested over 4 years.
• 401(k) match.
• Monthly wellness stipend.
• Fully remote work environment.