- Company Name
- Crossing Hurdles
- Job Title
- AI Penetration Tester | $111/hr Remote
- Job Description
-
**Job Title**
AI Penetration Tester
**Role Summary**
Conduct advanced adversarial testing of AI models and agents, including jailbreak creation, prompt injection, misuse scenario development, and systemic risk assessment. Produce high‑quality annotated data, reproducible reports, and actionable threat intelligence across multiple client projects.
**Expectations**
* Deliver consistent, rigorous red‑team assessments on an hourly contract basis.
* Rapidly absorb new AI technologies and adapt testing frameworks to evolving deployment contexts.
* Communicate findings clearly to technical stakeholders through comprehensive documentation and datasets.
**Key Responsibilities**
1. Red‑team AI systems by designing and executing jailbreaks, prompt injections, RLHF/DPO attacks, and model extraction exploits.
2. Generate annotated datasets that capture AI failures, classify vulnerabilities, and identify systemic risks.
3. Apply structured taxonomies, benchmarks, and playbooks to maintain consistency in testing across projects.
4. Document test outcomes and create reproducible reports, datasets, and attack case studies.
5. Support diverse projects, including LLM jailbreak testing and socio‑technical abuse scenarios, on a flexible, asynchronous schedule.
**Required Skills**
* Prior red‑team or adversarial ML experience (AI, cybersecurity, or socio‑technical probing).
* Deep understanding of jailbreak datasets, prompt injection techniques, RLHF/DPO attacks, and model extraction methods.
* Proficiency in penetration testing, exploit development, reverse engineering, and cybersecurity fundamentals.
* Knowledge of socio‑technical risk areas: harassment, disinformation, abuse analysis.
* Creative, psychology‑based probing (acting, writing, unconventional adversarial methods).
**Required Education & Certifications**
* Bachelor’s degree or higher in Computer Science, Cybersecurity, Artificial Intelligence, or related field (preferred).
* Relevant certifications such as Certified Ethical Hacker (CEH), Offensive Security Certified Professional (OSCP), or equivalent are advantageous.