AI Instructor – Red teaming

YPAI; United States; Remote; USD 36,000 - 136,000; Full time

Job summary

YPAI Learn conducts live online classes for testing AI systems, teaching students to identify failures safely within scope. Classes are delivered in English from a prepared kit, remotely, with payment per class.

Instructors lead sessions such as red-team planning and reproducible reporting, guiding learners through findings and reports with controlled demo probes. Prior teaching or security workshop experience is valued, with flexible scheduling and pay per class.

Responsibilities

• Teach the live class “Plan and run a scoped red-team session on an AI assistant”, 90 minutes, from the class kit.
• Teach the live class “Write a reproducible report for a model failure”, 90 minutes, from the class kit.
• Show live how to probe the demo assistant one category at a time, such as prompt injection, jailbreak framing, privacy leaks and unsafe advice, and stop once the failure is proven.
• Walk learners through a finding report: exact prompts, model and settings, steps, expected and observed behaviour, how often it reproduces and a severity rating.
• Help learners who drift outside the scope, cannot reproduce a result they saw once, or are unsettled by disturbing output during testing.

Job description

Teach live online classes on red teaming AI systems: looking for failures and unsafe behaviour on purpose, safely and within an agreed scope, and reporting each finding so others can reproduce it. You teach in English from a ready class kit, remotely, and you are paid for each class you teach.

What the work is for

YPAI Learn runs live classes for people who test AI systems. Your classes take learners from random attempts to break a chatbot to a planned session with a written scope, and teach them to check that every finding reproduces and is reported without spreading harmful detail.

The work

• Teach the live class “Plan and run a scoped red-team session on an AI assistant”, 90 minutes, from the class kit.
• Teach the live class “Write a reproducible report for a model failure”, 90 minutes, from the class kit.
• Show live how to probe the demo assistant one category at a time, such as prompt injection, jailbreak framing, privacy leaks and unsafe advice, and stop once the failure is proven.
• Walk learners through a finding report: exact prompts, model and settings, steps, expected and observed behaviour, how often it reproduces and a severity rating.
• Help learners who drift outside the scope, cannot reproduce a result they saw once, or are unsettled by disturbing output during testing.

What to expect

• You lead every class live and online, in English, for an international group. The application also asks which further languages you could teach in.
• The kit for every class contains a minute-by-minute plan, slides, speaker notes, a demo of probing an assistant and a backup recording in case the live demo fails.
• Teaching is remote: your own computer, a steady connection, a camera and a microphone, and a browser to run the demo in.
• You pass the instructor test for the class before you lead it the first time.
• Before a teaching assignment starts, you sign an instructor agreement. It covers pay, confidentiality and how class material may be used.
• Each invitation states the class times and the price learners pay, and you see both before you accept.

What you bring

• A red-team finding or test plan you can show, from public work, a bug bounty or a made‑up target, with the report you wrote.
• Experience teaching, running security or safety workshops, or training testers.
• Patience with learners who expect one clever prompt to do the work of a test plan.

You need

• Hands‑on red‑team­ing or adversarial testing of AI models or AI products in real work.
• Sound judgement on responsible disclosure and on handling harmful content, so you can show safe testing in front of learners.
• Fluent spoken English, the language the classes are taught in.
• 18 years or older.

Good to know

• Some employment contracts require approval for side work; if yours does, sort it out before you say yes to an assignment.
• Class demand decides how often you teach; every invitation states how much time it is expected to take.
• Applying is free. You are not asked to buy or take a YPAI Learn course.

Pay

$26–$99/hr. Rate shown is for the United States. This role is open in 4 countries, with local rates; pick your country on YPAI.

YPAI pays every two weeks for approved work via PayPal, Wise or bank transfer. Work is by invitation after your profile is reviewed.