Senior Offensive Security Engineer: Red Team & Pentest

Perplexity; New York (NY); On-site; USD 220,000 - 405,000; Full time

Job summary

Perplexity is seeking a highly skilled Offensive Security Engineer to join our security team. You’ll plan and execute red team operations, penetration tests, and adversarial simulations across our cloud infrastructure, web and mobile apps, AI/ML pipelines, and corporate environment—driving remediation with engineering teams.

You will develop custom tooling, run open-scope simulations, and contribute to CI/CD security and secrets management.

Qualifications

• 5+ years hands-on experience in offensive security, red teaming, or penetration testing.
• Deep expertise in at least two areas among cloud security (AWS/GCP/Azure), web/API security, Kubernetes and container security, macOS/Linux endpoint security, network pen testing, or CI/CD security.
• Strong programming and scripting skills in Python or Go; ability to write custom tooling and exploits.
• Experience with industry-standard offensive tools (Burp Suite, Cobalt Strike/Sliver/Mythic, Metasploit, BloodHound, nuclei, etc.) and ability to operate beyond them.
• Excellent written and verbal communication; ability to translate complex findings into clear risk narratives.
• Experience assessing AI/ML systems, LLM applications, or agentic workflows for security vulnerabilities.

Responsibilities

• Plan and execute red team and purple team engagements across cloud, endpoints, and apps.
• Conduct continuous penetration testing of web apps, APIs, mobile clients, browser extensions, cloud infrastructure, and internal services.
• Assess AI/ML attack surfaces including prompt injection, model exfiltration, agent abuse, tool-use exploitation, and MPC security boundaries.
• Develop and maintain custom offensive tooling, exploits, and automation to improve testing efficiency.
• Perform open-scope adversary simulations that test detection and response end-to-end, collaborating with the defensive security team.
• Drive threat modeling sessions with engineering to identify and prioritize attack vectors in new features.
• Deliver clear, actionable findings to technical and executive audiences; validate remediations with engineering.
• Contribute to the security of CI/CD pipelines, supply chain integrity, and secrets management through offensive assessment.
• Stay current on emerging attack techniques and adversary tradecraft.

Skills

Offensive security

Red teaming

Penetration testing

Threat modeling

Cloud security

Web/API security

Kubernetes security

Python

Go

CI/CD security

Tools

Burp Suite

Cobalt Strike

Sliver

Mythic

Metasploit

BloodHound

Nuclei

Job description

Perplexity is seeking a highly skilled Offensive Security Engineer to join our security team. You’ll plan and execute red team operations, penetration tests, and adversarial simulations across our cloud infrastructure, web and mobile apps, AI/ML pipelines, and corporate environment—driving remediation with engineering teams.

You will develop custom tooling, run open-scope simulations, and contribute to CI/CD security and secrets management.