Responsible AI / Security Specialist

$90–140/hr

rate as listed

Workload: 20+ hrs/week
Engagement: Project-based
Location: US
Field: STEM and Coding

Create and evaluate adversarial security tasks used to improve large language models, with a focus on vulnerabilities, unsafe behavior and policy violations. The role combines hands-on security expertise with rubric design, technical writing and review of AI-generated solutions.

The work

You would design security and responsible AI tasks, write reference solutions, and evaluate model responses for technical accuracy, safety and potential harm. Day-to-day work may include developing red-team scenarios, reviewing secure code or offensive-security reasoning, identifying policy violations, writing assessment rubrics and giving technical feedback to research and engineering teams.

What the screen is likely to test

The platform will look for at least four years of dedicated professional experience in cybersecurity, red teaming, penetration testing, threat intelligence or trust and safety at a recognized, top-tier organization. Expect follow-up on specific engagements, your personal contribution, evidence of career progression and hands-on depth in at least one named area: application security and secure code review, penetration testing and offensive security, threat intelligence or incident response, or trust and safety policy enforcement. Credentials such as OSCP, OSWE, GPEN or CISSP, along with published CVEs, bug bounty findings or security research, are strong pluses rather than stated requirements.

Practical details

This is W-2 employment with Cincinnatus LLC, with potential placement at a leading AI lab as part of its extended workforce. Candidates must be able to work reliably for at least 20 hours per week during weekdays. The listing does not specify whether the work is remote, whether collaboration is primarily asynchronous or how hours are distributed across the week.

Pay band: $90–140/hr

What they look for

4+ years of dedicated professional experience in cybersecurity, red teaming, penetration testing, threat intelligence or trust and safety
Hands-on expertise in application security, offensive security, threat intelligence, incident response or trust and safety policy enforcement
Adversarial scenario and red-team task design for AI systems
Security evaluation rubric design and model-response assessment
Clear written explanations of complex technical and safety decisions
Demonstrable career progression in relevant security or trust and safety work

Included with this listing

Interview prep — 10 questions

Matched to what this platform's screening actually measures. Answer each out loud in 60–90 seconds: claim → concrete example → implication.

What it tests: This tests whether your timeline meets the experience threshold and shows increasing scope rather than repeated exposure to the same level of work.
A strong answer: Give a dated progression through relevant roles, naming the organization type, your individual remit and how your ownership or technical complexity increased. Separate work you performed directly from outcomes delivered by the wider team.
Where people lose it: Candidates lose points by listing employers and project names without establishing duration, individual contribution or evidence of progression.

Summary, eligibility guidance and screening preparation are prepared by Sidequest from the platform's posting. Check the source listing before applying.

STEM AND CODING on Sidequest

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