Lead Assistant Manager

Job Title: Lead Assistant Manager Offensive Security (IC Role)

We are looking for a skilled offensive security professional to take a leading role in executing and enhancing our offensive security operations. This is an individual contributor (IC) position, with Lead reflecting the expectation to drive engagements technically and operationally not people management.

The ideal candidate will have 35 years of hands-on experience in red teaming, adversary simulation, or penetration testing, with a solid understanding of attacker tradecraft and the ability to execute advanced offensive assessments. You will be responsible for planning, executing, and reporting on offensive engagements that accurately reflect real-world threats, working closely with internal teams to strengthen detection and response capabilities.

Key Responsibilities

• Lead offensive security engagements end-to-end from scoping and planning to execution and reporting.
• Conduct red team and adversary emulation campaigns across infrastructure, applications, and cloud environments.
• Identify and exploit security gaps using realistic tactics, techniques, and procedures (TTPs) such as privilege escalation, lateral movement, and domain dominance.
• Participate in Purple Team exercises to enhance defensive detection and response.
• Maintain and improve offensive methodologies, tools, and playbooks.
• Deliver high-quality technical reports and concise executive summaries, clearly outlining attack paths, risks, and recommendations.
• Keep up to date with evolving attack techniques and integrate them into testing activities.
  
  

Experience

• 35 years of experience in red teaming, penetration testing, or other offensive security roles.
• Proven ability to execute and coordinate complex offensive security operations.
• Hands-on experience with enterprise environments, including Active Directory and cloud platforms.
  
  

Technical Skills

• Strong understanding of Windows and Linux internals, enterprise AD security, and common cloud attack surfaces.
• Proficiency in offensive techniques: lateral movement, domain escalation, Kerberoasting, delegation abuse, and token manipulation.
• Experience with C2 frameworks (e.g., Cobalt Strike, Sliver, Mythic) and post-exploitation tradecraft.
• Familiarity with tools such as BloodHound, Mimikatz, Rubeus, Responder, SharpHound, and Burp Suite.
• Working knowledge of the MITRE ATT&CK framework.
• Scripting skills in PowerShell, Python, or Bash for automation and PoC development.
  
  

Communication & Reporting

• Strong technical documentation skills, translating offensive findings into clear, actionable reports.
• Ability to explain technical vulnerabilities and attack paths to both technical teams and leadership.
  
  

Preferred Qualifications

• Experience with Purple Team exercises.
• Familiarity with threat intelligenceled testing methodologies.
• Exposure to AppSec testing.
• Relevant certifications (e.g., OSCP, CRTO, CRTP, OSEP) are a plus.