Senior Offensive Security Lead – Attack Simulation

Cyber Security Agency of Singapore (CSA); Singapore; On-site; SGD 120,000 - 180,000; Full time

Job summary

Cyber Security Agency of Singapore (CSA) is seeking a senior offensive security practitioner to lead realistic attack simulations and complex assessments across web, mobile, infrastructure, cloud, OT, and telecom environments.

The successful candidate will execute adversary-led engagements end-to-end, mentor junior consultants, and help evolve ASG methodologies and tooling while contributing to national cyber resilience in Singapore.

Qualifications

• 5–8 years of relevant experience in penetration testing, red team operations, or related offensive security roles.
• Proven ability to identify and execute real-world attack scenarios, beyond automated testing.
• Experience in penetration testing and/or red team operations, with exposure to adversary tradecraft.
• Demonstrated adaptability to transfer skills across technical domains (web, mobile, cloud, OT).

Responsibilities

• Lead and conduct penetration testing, red teaming, and adversary simulation activities across web, mobile, infrastructure, cloud, OT, and telecommunications environments.
• Execute realistic attack scenarios to assess the resilience of Critical Information Infrastructure (CII).
• Support purple‑teaming activities by translating offensive techniques into actionable detection and response improvements.
• Lead engagements end-to-end, including planning, execution, reporting, and technical debriefs with stakeholders.
• Mentor junior consultants and contribute to raising the team’s overall technical standard.
• Drive continuous improvement of ASG’s testing methodologies, tooling, and research, including taking on problem spaces outside your primary domain when required.
• Be prepared to occasionally switch gears by contributing to strategic initiatives, procurement activities, industry outreach, or coordination work.

Skills

Offensive security

Penetration testing

Red teaming

Adversary tradecraft

Technical writing

Job description

Cyber Security Agency of Singapore (CSA) is seeking a senior offensive security practitioner to lead realistic attack simulations and complex assessments across web, mobile, infrastructure, cloud, OT, and telecom environments.

The successful candidate will execute adversary-led engagements end-to-end, mentor junior consultants, and help evolve ASG methodologies and tooling while contributing to national cyber resilience in Singapore.