Senior Offensive Security Engineer - Red Team Lead

Iceberg; Chicago (IL); Hybrid; USD 140,000 - 210,000; Full time

Job summary

Iceberg in Chicago is seeking a Senior Offensive Security Engineer to join a highly technical global financial organisation building out its offensive security capability. This role requires thinking like an attacker, not merely running automated pentesting tools.

You’ll own engagements from reconnaissance through exploitation and lateral movement, collaborating with infrastructure, development and security teams to remediate and retest issues.

Qualifications

• 5+ years of hands-on offensive security experience.
• Ability to take engagements from recon to exploitation, privilege escalation and lateral movement.
• Strong communication and collaboration with engineering teams.

Responsibilities

• Red teaming and adversary simulation.
• Penetration testing across infrastructure, applications, APIs and cloud.
• Exploiting vulnerabilities across Windows, Linux and macOS environments.
• Building your own offensive tooling alongside using established tools.
• Working closely with defensive teams on purple team exercises.
• Owning vulnerability remediation through to resolution.
• Testing emerging attack vectors including AI and LLM environments.
• Helping shape the wider offensive security methodology and roadmap.

Skills

Offensive security

Red teaming

Penetration testing

Cloud security

Job description

Iceberg in Chicago is seeking a Senior Offensive Security Engineer to join a highly technical global financial organisation building out its offensive security capability. This role requires thinking like an attacker, not merely running automated pentesting tools.

You’ll own engagements from reconnaissance through exploitation and lateral movement, collaborating with infrastructure, development and security teams to remediate and retest issues.