Jailbreak Pattern Catalogue (Notion)

About this task

This health insurer for homeowners (51–200 employees) is looking for a senior Red-Teamer for a rating and review programme for AI output in your own field, 3–8 h a week. Groups attacks into patterns that guide defences.

Ratings are checked against a written rubric, and your notes go back to the team that builds the product. It is an insurer, so accuracy and an audit trail come before speed.

The work is fully remote. Any location in Canada works, with a few hours of overlap with the team's day.

What you deliver

• Organise 120 successful attacks into a catalogue of patterns with examples.
• Ratings entered in the client's tool against the written rubric, with a one-line reason each
• A weekly count of items reviewed, confirmed by the programme lead
• Short calibration notes after the first batch, so your ratings match the guidelines

What a week looks like

• Wednesday: 15-minute check-in to agree the week's items
• Friday: main working block (3 hours)
• Thursday: hand-off note with what shipped and what is open

Duration: Weekly batches for 12 weeks, renewed every four weeks. Accepted on the company's written OK. If something is missed, you fix it in the same week at no extra charge to either side.

Tools

How you get paid

• The company prepays Deftridge before your first hour, so payment does not depend on a late invoice.
• Deftridge pays you in CAD after the company confirms the hours or the deliverable. The payment date is written in your task agreement.
• You work as an independent contractor: you report your own income, and your recruiter sends the statements your accountant needs.
• You never chase the company. Questions about money go to Deftridge.

What happens after you say you're interested

1. Within one working dayA recruiter writes to you to confirm your hours and the rate you want.
2. You agree the rateYou and the recruiter fix an exact rate inside the company's range. You decide whether to go ahead.
3. With your written OKThe company sees the anonymous profile below. Most companies answer within three working days.
4. StartYou sign the task agreement and the company's confidentiality terms through Deftridge, and begin on the date above.

What the company sees about you

First name, field, experience, tools and the hours you offer. Not your surname, your employer or your contact details.

How this rate compares

The midpoint of this range, CA$65 an hour, is in line with the median senior Red-Teamer rate in Canada (CA$65). The shaded band is the 25th to 75th percentile of the market.

All Red-Teamer jobs in Canada · Red-Teamer rates in Canada · AI Expert Review jobs

Questions about pay and privacy

The rules are the same for every task. Pricing explains the 15% fee, prepayment and when you are paid; How it works covers matching, what the company sees and side work next to a job.