Principal Red Team Operator

Armadin•Palo Alto, CA

2d•Onsite

About The Position

Armadin is building autonomous proactive security products that use specialized AI agents to discover, exploit, and chain vulnerabilities across external, internal, identity, cloud, and application attack surfaces. The agents operate continuously against live production environments. The Principal Red Team Operator will perform hands-on operations and encode expert tradecraft into the reasoning used by the agents, helping them identify footholds, exploit application logic, pivot through identity, distinguish exploitable issues from scanner noise, and assess blast radius. The role pressure-tests complete attack chains, identifies where the agent swarm falls short, and helps train it to operate more like an expert. The operator will work with experienced red teamers and AI engineers in a small, high-ownership team, collaborating with product engineering to translate offensive security needs into platform capabilities and AI-driven attack simulations. The position is onsite in Palo Alto, California. The role also includes technical leadership, research, reporting, product strategy input, open-source and proprietary tool development, industry representation, client executive communication, and participation in hiring and mentoring. Armadin offers full health, dental, and vision coverage, equity ownership, in-office meals, office haircuts, company-sponsored conferences and events, 401(k), HSA and FSA plans, and flexible PTO.

Requirements

At least 8 years of hands-on offensive security experience, with extensive depth across multiple disciplines.
Advanced web application penetration testing and secure code review, including OWASP Top 10, business logic flaws, authentication and authorization bypass, API security, and control flow analysis.
Network penetration testing, Active Directory attacks, lateral movement, privilege escalation, and persistence across enterprise infrastructure.
Mobile application security assessments, thick/thin client reverse engineering, and binary analysis across iOS, Android, Windows, macOS, and Linux.
Cloud infrastructure security, identity systems such as Kerberos, SAML, and OAuth, and multi-cloud red team operations.
Ability to integrate findings across multiple attack surfaces into comprehensive strategic offensive campaigns.
Expert-level proficiency with offensive security tools across multiple domains, such as Burp Suite, OWASP ZAP, Caido, Nmap, Metasploit, Cobalt Strike, Impacket, BloodHound, Responder, CrackMapExec, Frida, Ghidra, and IDA Pro.
Advanced scripting and tool development in Python, Bash, PowerShell, or compiled languages; ability to extend C2 frameworks, develop custom exploits, and create application-specific tooling.
Deep understanding of network protocols, packet-level analysis, cryptography, system architecture, and application design patterns.
Proficiency with Windows, Linux, and macOS; container technologies; and cloud environments including AWS, Azure, and GCP.
Willingness to work onsite in the Palo Alto, California office.
Exceptional written and verbal communication skills, including the ability to explain complex technical concepts to executives, product teams, and diverse client audiences.
Strategic thinking and ability to align technical initiatives with business objectives; experience influencing product roadmaps or organizational strategy.
Experience providing technical mentorship and guidance.

Nice To Haves

Prior experience working alongside AI/ML models, automated offensive security frameworks, or building AI-augmented attack tools.
Published research, conference speaking, or significant open-source contributions in offensive security.
Experience in startup or high-growth environments, with the ability to take on multiple roles and drive initiatives with minimal bureaucracy.
Advanced certifications such as OSCP, OSCE, CRTE, CRTO, or equivalent elite-level credentials.
Track record of building offensive security tools or frameworks adopted by the community.

Responsibilities

Execute sophisticated, multidisciplinary red team engagements across application security, network penetration testing, cloud infrastructure, and identity systems.
Identify novel attack chains and weaknesses through source code review, network analysis, binary reverse engineering, and infrastructure assessment.
Prepare technically rigorous reports and executive briefings that communicate findings, remediation roadmaps, and risk narratives to technical and non-technical audiences.
Conduct threat analysis and intelligence gathering covering enterprise attack surfaces, adversarial TTPs, business risk, and compliance implications.
Share tradecraft, tool development insights, and lessons learned to improve team capability.
Collaborate with product engineering and AI teams to translate red team needs and adversarial insights into platform capabilities, tool integrations, and AI-driven attack simulations.
Represent offensive security tradecraft in product strategy discussions and help prioritize real-world attack complexity and operator efficiency.
Lead research into emerging attack vectors, exploitation techniques, AI-augmented adversarial methods, and tools.
Develop and contribute to open-source tooling, proprietary frameworks, and methodologies.
Represent Armadin through conference talks, published research, security community engagement, and technical leadership.
Communicate strategic security findings, risk narratives, and business implications to executive leadership and client C-suite stakeholders.
Contribute to hiring, interviewing, and technical assessment of prospective red team operators.
Pressure-test end-to-end kill chains, identify weaknesses in the agent swarm, and encode expert tradecraft into the agents’ reasoning.