Head of Trust & Safety

Magic School, Inc.; United States; Remote; USD 180,000 - 280,000; Full time

Benefits offered by this job

Unlimited time off

Employer-paid health insurance

Stock options

401k match

Wellness stipend

Job summary

MagicSchool is seeking a Senior Trust & Safety leader to own the safety of AI outputs across teacher and student products. You will develop policy, guardrails, evaluation pipelines, and incident response, while aligning with state guidance and COPPA/FERPA requirements.

Build and scale a small safety team and partner with Legal to address regulatory needs. You will drive safety as product infrastructure, enabling faster, confident ship cycles and serving diverse districts globally.

Qualifications

• Proven ownership of trust & safety for a consumer or youth-facing product at scale.
• Hands-on with LLM safety tooling, including evals and red-teaming.
• Experience building safety into product infrastructure, not as a gate.
• Ability to communicate safety tradeoffs clearly to executives and districts.
• Strong written safety documents and district-facing explainers.

Responsibilities

• Own the safety of AI output for teachers and students: policy, guardrails, evals, red-teaming, incident response.
• Own trust posture with districts: safety docs, RFP responses, and alignment with guidance.
• Develop safety evaluations and monitoring as part of product infra with acceptance criteria.
• Oversee student-facing safety: age-appropriate content, crisis handling, escalation paths.
• Lead safety incident process end-to-end and drive postmortems into product/engineering.
• Collaborate with Legal on COPPA, FERPA, and state privacy laws; ensure compliance posture.
• Build and lead a small team (1–3 initially); scale the function through 2027.

Skills

Trust & safety ownership

LLM safety tooling

Policy & guardrails

Executive communication

Safety documentation

Ambiguity decision making

Tools

Datadog

Notion

Linear

Slack

Vercel

PostgreSQL

Job description

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 that is working towards real social impact. Make an account and try us out at our website and connect with our passionate community on our Wall of Love.

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. T&S 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 / COMPETENCIES / 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 say what to change.
• 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 exec team.
• Strong writer: safety docs, district-facing explainers, incident communications.
• Operates hypothesis-first and escalates one-way doors fast rather than sitting on them.

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.

REQUIRED EXPERIENCE

• Proven ownership of trust & safety or responsible AI at a consumer or youth-facing product at scale.
• Hands-on experience with LLM safety tooling: evals, classifiers, and red-teaming.
• Experience handling live incidents involving minors or vulnerable users.
• Track record of building safety as product infrastructure, not a gate.
• Demonstrated ability to communicate safety tradeoffs clearly to executive and district-level audiences.

TECH STACK

• LLM layer: multi-provider (OpenAI / Anthropic / Google via GCP Vertex); moderation APIs and custom classifiers.
• 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 and knowledge tooling: Linear, Slack workflows, Notion.

Why Join Us?

• Work on cutting-edge AI technology that directly impacts educators and students.
• Join a mission-driven team passionate about making education more efficient and equitable.
• Flexibility of working from home, while fostering a unique culture built on relationships, trust, communication, and collaboration with our team - no matter where they live.

For full time employees:

• Unlimited time off to empower our employees to manage their work-life balance. We work hard for our teachers and users, and encourage our employees to rest and take the time they need.
• Choice of employer-paid health insurance plans so that you can take care of yourself and your family. Dental and vision are also offered at very low premiums.
• Every employee is offered generous stock options, vested over 4 years.
• 401k match & monthly wellness stipend.

Our Values:

• Educators are Magic: Educators are the most important ingredient in the educational process - they are the magic, not the AI. Trust them, empower them, and put them at the center of leading change in service of students and families.
• Joy and Magic: Bring joy and magic into every learning experience - push the boundaries of what’s possible with AI.
• Community: Foster community that supports one another during a time of rapid technological change. Listen to them and serve their needs.
• Innovation: The education system is outdated and in need of innovation and change - AI is an opportunity to bring equity, access, and serve the individual needs of students better than we ever have before.
• Responsibility: Put responsibility and safety at the forefront of the technological change that AI is bringing to education.
• Diversity: Diversity of thought, perspectives, and backgrounds helps us serve the wide audience of educators and students around the world.
• Excellence: Educators and students deserve the best - and we strive for the highest quality in everything we do.