Senior Red Team Trainer

 A Cybersecurity training provider is looking for a Senior Red Team Trainer for 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

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

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

4. 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.

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

6. Custom Cyber Range Design & Execution

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

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

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

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

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

1. 
   

2. Consulting & Proof-of-Concept Engagements

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

4. 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.

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

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

7. Client Relationship Management & Stakeholder Communication

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

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

10. 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.

---