Penetration Tester

Penetration Tester is a remote review track for evaluating AI outputs across penetration tester specialist operations workflows. Reviewers grade workflow correctness, policy adherence, and stakeholder fit; flag operational risk; and document the right next step so the modeling team can train on it.

Category:
Enterprise Workflow & Tool Use
· Pay: $85 / hr
·

Location:

Remote — US-eligible
· Contractor

Penetration Tester is a remote review track for evaluating AI outputs across penetration tester specialist operations workflows.

Penetration Tester is a remote review track for evaluating AI outputs across penetration tester specialist operations workflows. Reviewers grade workflow correctness, policy adherence, and stakeholder fit; flag operational risk; and document the right next step so the modeling team can train on it.
Penetration Tester specialist operations AI has to fit into an actual day aOne uses experienced operators to grade outputs the way a senior peer would — checking workflow, policy, and the unwritten rules that decide whether a task actually gets done.
Judge tool-use tasks and enterprise agent behavior. Operational judgment is the skill.

• Review AI outputs against current penetration tester specialist operations workflows, playbooks, and firm policy for Penetration Tester assignments.
• Grade tone, escalation logic, and stakeholder fit on a structured rubric.
• Flag operational risk, missed escalations, and policy-adherence gaps with severity tags.
• Capture the right next step so the modeling team can train on it.
• Adjudicate disputed treatments against published playbooks or firm guidance.

• Direct working experience in penetration tester specialist operations on real teams for Penetration Tester work.
• Comfort applying multi-page rubrics consistently across long batches.
• Clear written reasoning that names the policy or workflow being applied.
• Strong attention to detail and the ability to flag when a prompt itself is the problem.
• Reliable async availability for at least 10 hours per week.

• Grade a model's response to a real penetration tester specialist operations ticket and rate workflow, tone, and escalation.
• Flag a missed escalation with the right severity tag and corrected next step.
• Adjudicate a disputed playbook call between two reviewers using firm guidance.
• Audit a 25-row batch for rubric consistency and report drift to the program lead.

• Prior experience training, calibrating, or QA-ing operations teams.
• Familiarity with AI-assisted workflow tooling and its failure modes.
• Bilingual experience for cross-region operations.

Hourly rate confirmed after the interview process.
Expected arrangement: contractor , with program-defined task volume and review pacing. Placement depends on current program demand and reviewer confirmation.

• Operational review
• Policy adherence
• Workflow judgment
• Stakeholder communication
• Penetration Tester specialist operations