Offensive Security Engineer — Cloud & AI Red Team

Perplexity; California (MO); On-site; USD 120,000 - 180,000; Full time

Job summary

Perplexity is seeking a highly skilled Offensive Security Engineer to join our security team and adopt an adversarial mindset to harden infrastructure, apps, and AI systems. You will plan and execute red team operations, penetration tests, and attack simulations across cloud, web, mobile, and AI pipelines.

You will work with engineering teams to drive remediation, develop tooling, and continuously improve detection and response capabilities across CI/CD, supply chain, and secrets management.

Qualifications

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

Responsibilities

• Plan and execute red team and purple team engagements simulating advanced threat actors across cloud infrastructure (AWS, Kubernetes), endpoints, and applications.
• Conduct continuous penetration testing of web apps, APIs, mobile clients, browser extensions, cloud infra, and internal services.
• Assess AI/ML-specific attack surfaces including prompt injection, model exfiltration, agent abuse, and tool-use exploitation.
• Develop and maintain custom offensive tooling, exploits, and automation to improve testing efficiency and coverage.
• Perform open-scope adversary simulations testing detection and response end-to-end, collaborating with the defensive team.
• Drive threat modeling sessions with engineering to identify and prioritize attack vectors in new features.
• Deliver clear findings to technical and executive audiences and validate remediations with engineering teams.
• Contribute to CI/CD security, supply chain integrity, and secrets management through offensive assessments.
• Stay current on new attack techniques and adversary tradecraft; bring external perspective to Perplexity's security strategy.

Skills

Offensive security

Red teaming

Penetration testing

Python

Go

Tooling development

Security research

AI/ML 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 and adopt an adversarial mindset to harden infrastructure, apps, and AI systems. You will plan and execute red team operations, penetration tests, and attack simulations across cloud, web, mobile, and AI pipelines.

You will work with engineering teams to drive remediation, develop tooling, and continuously improve detection and response capabilities across CI/CD, supply chain, and secrets management.