Ensign is hiring !
Description
The Manager, Advanced Adversarial Simulation leads the design, build, and execution of advanced red teaming capabilities that emulate real-world adversaries across the full attack lifecycle. This role is responsible for developing a high-performing team capable of end-to-end delivery—from engagement scoping and adversary design, through tool and infrastructure development, to execution and reporting of sophisticated red team operations.
You will own both the technical outcomes and the people outcomes of the team. This includes advancing internal red teaming platforms and automation (e.g. C2 infrastructure, tooling, AI-assisted tradecraft), delivering high-impact adversarial simulations for clients, and growing consultants into trusted, senior-level red teamers.
This is a hands-on leadership role that blends deep technical expertise with delivery excellence, capability building, and mentorship.
Roles and Responsibilities
Technical & Delivery Leadership
Lead the planning and execution of advanced red team and adversarial simulation engagements, covering the full lifecycle from scoping and threat modelling to execution, reporting, and executive debriefs.
Design realistic adversary emulation scenarios aligned to real-world threat actors, business objectives, and client risk profiles.
Oversee and contribute to the development of internal red team tooling, including:
Command-and-control (C2) frameworks and infrastructure
Payload delivery and post-exploitation tooling
Infrastructure automation and operational security (OPSEC)
AI-enabled automation to augment reconnaissance, exploitation, and decision-making
Ensure engagements are executed safely, ethically, and to a high technical and professional standard.
Capability & Platform Development
Build and mature reusable red teaming platforms, automation, and workflows that improve scale, quality, and consistency of delivery.
Drive innovation in adversarial simulation techniques, including the responsible use of AI, automation, and novel attack paths.
Establish and maintain technical standards, playbooks, and operational processes for advanced red teaming.
People & Team Leadership
Lead, mentor, and grow a team of red team consultants and engineers, developing both technical depth and professional maturity.
Set clear expectations, provide structured feedback, and actively coach consultants toward senior and principal-level capabilities.
Identify skills gaps and drive targeted training, research, and capability uplift across the team.
Foster a culture of rigour, curiosity, collaboration, and accountability.
Stakeholder & Engagement Management
Act as a trusted technical leader for internal stakeholders and clients, clearly articulating risks, findings, and strategic implications.
Support pre-engagement scoping, proposal development, and estimation for advanced adversarial simulation work.
Partner with adjacent teams (e.g. blue team, threat intelligence, engineering) to enable purple teaming and continuous improvement.
Accountability & Governance
Own delivery quality, outcomes, and client satisfaction for advanced adversarial simulation engagements.
Ensure documentation, reporting, and evidence meet internal quality standards and client expectations.
Contribute to practice-level strategy, roadmap planning, and long-term capability development.
Requirements
Experience
8+ years of experience in offensive security, red teaming, or adversary simulation, with demonstrated leadership of complex engagements.
Proven experience leading or mentoring teams in a consulting or professional services environment.
Hands-on experience delivering advanced red team operations across enterprise environments (on-prem, cloud, hybrid).
Technical Expertise
Deep understanding of attacker tradecraft across the cyber kill chain, including reconnaissance, initial access, persistence, privilege escalation, lateral movement, and impact.
Strong experience with red team tooling, C2 frameworks, and infrastructure design.
Practical experience building or automating offensive tooling, infrastructure, or workflows (e.g. C, C++, C#, Python, Go, PowerShell, or similar).
Working knowledge of cloud platforms, identity systems, and modern enterprise security controls.
Familiarity with AI-assisted security tooling or automation is strongly preferred.
Leadership & Communication
Demonstrated ability to lead high-performing technical teams and develop consultants over time.
Strong communication skills, with the ability to translate complex technical findings into clear, risk-focused narratives for technical and executive audiences.
Comfortable owning outcomes, making decisions in ambiguous environments, and balancing innovation with operational discipline.
Mindset
Strong sense of ownership and accountability for both delivery quality and team growth.
Passion for building sustainable, scalable red teaming capabilities—not just running one-off engagements.
Curious, adaptable, and committed to continuous improvement in both technology and people.
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What We Do
Ensign InfoSecurity is the largest pure-play end-to-end cybersecurity service provider in Asia. Headquartered in Singapore, Ensign offers bespoke solutions and services to address their clients’ cybersecurity needs. Their core competencies are in the provision of cybersecurity advisory and assurance services, architecture design and systems integration services, and managed security services for advanced threat detection, threat hunting, and incident response. Underpinning these competencies is in-house research and development in cybersecurity. Ensign has two decades of proven track record as a trusted and relevant service provider, serving clients from the public and private sectors in the Asia Pacific region
