[Hiring] AI Safety Expert @Weekday AI

Role Description

This role is for one of our clients.

Compensation: $48 - $62 per hour

Fluent Language Skills Required: English & Finnish. Native fluency in English and Finnish is required for this position.

Why This Role Exists:

• We are assembling a red team for this project - human data experts who probe AI models with adversarial inputs, surface vulnerabilities, and generate the red team data that makes AI safer for our customers.
• This project involves reviewing AI outputs that touch on sensitive topics such as bias, misinformation, or harmful behaviors.
• All work is text-based, and participation in higher-sensitivity projects is optional and supported by clear guidelines and wellness resources.
• Before being exposed to any content, the topics will be clearly communicated.

What You’ll Do:

• Red team conversational AI models and agents: jailbreaks, prompt injections, misuse cases, bias exploitation, multi-turn manipulation.
• Generate high-quality human data: annotate failures, classify vulnerabilities, and flag systemic risks.
• Apply structure: follow taxonomies, benchmarks, and playbooks to keep testing consistent.
• Document reproducibly: produce reports, datasets, and attack cases customers can act on.

Qualifications

• You bring prior red teaming experience (AI adversarial work, cybersecurity, socio-technical probing).
• You’re curious and adversarial: you instinctively push systems to breaking points.
• You’re structured: you use frameworks or benchmarks, not just random hacks.
• You’re communicative: you explain risks clearly to technical and non-technical stakeholders.
• You’re adaptable: thrive on moving across projects and customers.

Nice-to-Have Specialties

• Adversarial ML: jailbreak datasets, prompt injection, RLHF/DPO attacks, model extraction.
• Cybersecurity: penetration testing, exploit development, reverse engineering.
• Socio-technical risk: harassment/disinfo probing, abuse analysis, conversational AI testing.
• Creative probing: psychology, acting, writing for unconventional adversarial thinking.

What Success Looks Like

• You uncover vulnerabilities automated tests miss.
• You deliver reproducible artifacts that strengthen customer AI systems.
• Evaluation coverage expands: more scenarios tested, fewer surprises in production.