-
Crossing Hurdles

Penetration Tester | Remote

Crossing Hurdles
Canada · Contract · Associate

Position: AI Red-Teamer — Adversarial AI Testing; English

Type: Hourly contract

Compensation: $50–$111 per hour

Location: Remote

Commitment: Full-time or part-time, flexible project-based engagement


Role Responsibilities

  • Conduct adversarial testing of AI models, including jailbreaks, prompt injections, misuse cases, and exploit discovery
  • Generate high-quality human evaluation data by annotating failures, classifying vulnerabilities, and flagging systemic risks
  • Apply structured red-teaming frameworks, taxonomies, benchmarks, and playbooks to ensure consistent testing
  • Produce clear, reproducible documentation such as reports, datasets, and adversarial test cases
  • Support multiple customer projects, ranging from LLM safety testing to socio-technical abuse and misuse analysis
  • Communicate identified risks and vulnerabilities clearly to technical and non-technical stakeholders


Requirements

  • Strong experience in AI red-teaming, adversarial testing, cybersecurity, or socio-technical risk analysis
  • Strong ability to probe systems creatively and systematically to uncover failure modes
  • Strong experience using structured evaluation frameworks rather than ad-hoc testing
  • Strong written communication skills with the ability to clearly document risks and findings
  • Comfort working across sensitive content areas such as bias, misinformation, or harmful behaviors
  • Ability to work independently in a remote, fast-moving project environment


Application Process (Takes 20 Mins)

  • Upload your resume.
  • Complete an interview.
  • Submit a short form.

Key Skills

Ranked by relevance

ai cybersecurity
Login to Apply
Posted
Feb 09, 2026
Type
Contract
Level
Associate
Location
Canada

Industries

Research Services Engineering Services

Categories

Information Technology Research

Related Jobs

3 roles aligned with this opportunity

View all jobs
View Job Details
Crossing Hurdles
Related

Software Engineer (AI-Native Platform & Integrations) | Remote

2026-05-23

Contract
Mid-Senior
Canada
Software Development
Engineering
View Job Details
Human Technopole
Related

DevOps Engineer

2026-05-18

Full-time
Not Applicable
Italy
Research Services
Engineering
View Job Details
Crossing Hurdles
Related

AI Data Reviewer | $40/hr Remote

2026-05-26

Contract
Associate
Turkey
Information Services
Administrative