Senior Red Team Trainer - Relocation to Singapore

As a Senior Trainer (Red Team Focus), you will design, develop, and deliver bespoke cyber training programs, oversee custom cyber range engagements, and provide ad-hoc cybersecurity consulting services. You will engage closely with clients during pre-sale, analyse their specific requirements, create comprehensive training materials and environments, lead hands-on sessions, mentor participants, and deliver detailed reports and presentations to stakeholders. Your offensive security expertise, combined with a consulting mindset, will be instrumental in crafting solutions that address each client’s unique challenges.

Key Responsibilities

1. Red Team Training Development & Delivery

• Collaborate with prospective clients to understand their operational goals, security maturity, and learning objectives.

• Design tailored red team curricula, including slide decks, hands-on labs, playbooks, and assessment criteria.

• Conduct immersive red team training sessions (instructor-led or virtual), guiding participants through advanced adversary-emulation techniques, custom exploit development, and stealthy post-exploitation methods.

• Prepare and present post-training deliverables—executive summaries, detailed findings, and recommendations—to client stakeholders.

2. Custom Cyber Range Design & Execution

• Lead early discussions to identify the client’s technical environment (on-premises, cloud, OT/ICS) and desired threat scenarios.

• Architect, build, and deploy realistic cyber range environments that replicate client infrastructure, including networks, endpoints, servers, and specialized systems.

• Develop and implement multi-phase attack scenarios, balancing complexity and learning outcomes for red and blue teams.

• Facilitate range activities, mentor participants throughout the engagement, and adapt scenarios dynamically based on participant progress.

• Deliver comprehensive after-action reports, highlighting technical observations, participant performance metrics, and actionable growth guidance.

3. Consulting & Proof-of-Concept Engagements

• Engage on ad-hoc client projects requiring specialized research, prototype development, or bespoke training modules.

• Conduct technical feasibility assessments, deliver proof-of-concept solutions (e.g., attack tools, detection rules, lab environments), and translate findings into training deliverables or code packages.

• Coordinate with client teams to define project scope, timelines, and success criteria.

• Present project outcomes, including demonstration of functionality, lessons learned, and strategic recommendations.

4. Client Relationship Management & Stakeholder Communication

• Serve as the primary point of contact for all engagement phases - planning, delivery, and post-delivery follow-up.

• Communicate effectively with executive-level stakeholders, technical teams, and internal colleagues to ensure alignment on objectives, deliverables, and timelines.

• Mentor and guide junior trainers, cyber range engineers, and analysts to foster continuous learning and skill development within the team.

Qualifications

• Professional Experience

• Minimum 10 years of hands-on red teaming or offensive security experience, with a proven track record of leading and executing complex assessments.

• Demonstrated expertise in adversary-emulation frameworks (e.g., MITRE ATT&CK), exploit development, phishing campaigns, lateral movement techniques, and stealthy post-exploitation. 

• Prior experience designing or delivering customized cybersecurity training programs and cyber ranges for enterprise or government clients.

• Consulting background preferred, including project scoping, SOW creation, and stakeholder management.

• Military experience is a major advantage

• Technical Skills

• Proficiency in at least one programming or scripting language (Python, C/C++, , Golang). Ability to develop or adapt tools, scripts, and lab environments.

• Strong understanding of network architecture, virtualization technologies (VMware, Nutanix), containerization, and cloud services (AWS, Azure, GCP).

• Experience building and managing infrastructure-as-code (Terraform, Ansible) for replicable lab or range deployments.

• Familiarity with industrial control systems (ICS/SCADA), telecommunication infrastructure and technologies used in critical infrastructure environments – an advantage.

• Communication & Presentation

• Exceptional written and verbal communication skills, with the ability to translate technical findings into clear, executive-level summaries.

• Proven capability to deliver engaging, interactive training sessions to audiences ranging from junior analysts to experienced security practitioners.

• Strong documentation skills—able to produce detailed lab guides, playbooks, and technical reports.

Desired Attributes

• Consultative Mindset: You listen actively to client challenges, propose pragmatic solutions, and align your recommendations to their business goals.

• Innovative Thinker: You proactively explore new offensive techniques, emerging tools, and novel training methodologies to keep content current and impactful.

• Collaborative Team Player: You work seamlessly with sales, engineering, and delivery teams, sharing knowledge and fostering a culture of continuous improvement.

• Adaptable Educator: You tailor your instruction style to individual learning preferences—whether in a classroom setting, virtual lab, or high-pressure executive briefing.

Detail-Oriented: You meticulously design labs and attack scenarios, ensuring every step mirrors real-world threats and maximizes learning outcomes.