Help leading AI labs build safer, more resilient models.

Parallel connects experienced cybersecurity specialists with projects supporting leading AI labs. We’re hiring an Enterprise Red Teamer to help AI systems accurately distinguish between benign and malicious cybersecurity prompts.

You’ll apply deep expertise in enterprise red teaming, adversary emulation, and network intrusion tradecraft to evaluate complex, ambiguous prompts. Your work will involve determining true user intent, assessing technical context, and providing clear annotations that improve model safety, training, and evaluation guidelines.

This is remote, project-based work. Engagements and hours vary with project demand, with scope and expected availability discussed before each assignment.

What you’ll do

• Review ambiguous cybersecurity prompts submitted to AI systems to determine the underlying intent and goal.
• Assess whether prompts reflect legitimate research and defensive purposes or malicious attack preparation.
• Apply deep domain expertise to evaluate the technical context, specificity, and real-world uplift a response would provide an attacker.
• Annotate prompts with accurate intent labels and clear, concise written rationales.
• Collaborate with other researchers through independent dual-annotation, escalating disagreements to a reviewer.
• Identify and flag emerging attack techniques, edge cases, and gaps in current project guidelines to improve the evaluation process.

What you’ll bring

• At least five years of hands-on experience in enterprise red teaming and adversary emulation.
• Deep knowledge of Active Directory attack paths, Kerberos abuse, credential access, lateral movement, and privilege escalation.
• Experience operating C2 frameworks (Cobalt Strike, Sliver, Mythic, Havoc) and building payloads and loaders that evade EDR/AV.
• Practical understanding of phishing and social engineering tradecraft, initial access techniques, and operational security (OPSEC).
• Fluency with the MITRE ATT&CK framework and the ability to differentiate red team operations from real-world intrusion activity.
• Strong analytical judgment and clear written communication in English to concisely document reasoning.
• Ability to work independently, manage details effectively, and solve complex, ambiguous problems.

Preferred experience

• Advanced offensive-security certifications such as OSEP, OSCP, or CRTO.
• Demonstrated online achievements, published security research, or technical write-ups.
• Contributions on platforms like HackTheBox, Bug Bounty programs, or similar security communities.

Selection process

Applicants must pass an assessment and complete a background check before engagement. Final compensation within the posted range will reflect relevant experience and demonstrated technical ability.