Senior Offensive Security Engineer: Red Team & AI/ML

Perplexity; San Francisco (CA); On-site; USD 220,000 - 405,000; Full time

Job summary

Perplexity is seeking a highly skilled Offensive Security Engineer to harden our infrastructure, applications, and AI systems. You’ll plan and execute red team operations, penetration tests, and attack simulations across cloud infrastructure, web and mobile applications, AI/ML pipelines, and internal networks.

You will collaborate with engineering to remediate vulnerabilities, drive threat modeling for new features, and deliver clear findings to technical and executive audiences.

Qualifications

• 5+ years of hands-on experience in offensive security, red teaming, or penetration testing.
• Deep technical expertise in at least two areas: cloud security, web/API security, Kubernetes/container security, macOS/Linux endpoints, network pen-testing, or CI/CD security.
• Track record of discovering impactful vulnerabilities or developing novel attack techniques in production environments.
• Strong programming and scripting skills in Python, Go, or similar languages; ability to write custom tooling and exploits.
• Experience with industry-standard offensive tools (Burp Suite, Cobalt Strike/Sliver/Mythic, Metasploit, BloodHound, nuclei).
• Excellent written and verbal communication; able to translate complex findings into clear risk narratives.
• Experience assessing AI/ML systems, LLM applications, or agentic workflows for security vulnerabilities.
• Bonus: Published security research, conference talks, CVE credits, or bug bounty contributions.

Responsibilities

• Plan and execute red team and purple team engagements across cloud infrastructure (AWS, Kubernetes), endpoints, and applications.
• Conduct continuous penetration testing of web applications, APIs, mobile clients, browser extensions, cloud infrastructure, and internal services.
• Assess AI/ML attack surfaces including prompt injection, model exfiltration, and agent abuse.
• Develop and maintain custom offensive tooling, exploits, and automation.
• Perform open-scope adversary simulations that test detection and response, partnering with the defensive 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 security of CI/CD pipelines, supply chain integrity, and secrets management.
• Stay current on emerging attack techniques and vulnerability research.

Skills

Red team operations

Penetration testing

Cloud security

Python/Go scripting

Tool proficiency

Tools

Burp Suite

Cobalt Strike

Sliver

Mythic

Metasploit

BloodHound

Nuclei

Job description

Perplexity is seeking a highly skilled Offensive Security Engineer to harden our infrastructure, applications, and AI systems. You’ll plan and execute red team operations, penetration tests, and attack simulations across cloud infrastructure, web and mobile applications, AI/ML pipelines, and internal networks.

You will collaborate with engineering to remediate vulnerabilities, drive threat modeling for new features, and deliver clear findings to technical and executive audiences.