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Key Responsibilities and Required Skills for Offensive Cybersecurity Instructor

💰 $90,000 - $160,000

CybersecurityTrainingOffensive SecurityInstruction

🎯 Role Definition

An Offensive Cybersecurity Instructor delivers high-impact, hands-on education in offensive security disciplines to corporate teams, government staff, and public students. This role combines deep technical expertise in penetration testing, red team operations, exploit development, and adversary emulation with proven instructional design and classroom delivery skills. The instructor is responsible for developing realistic lab environments, authoring courseware and assessments, conducting live demonstrations and exercises, and mentoring students to measurably raise their offensive security capabilities while maintaining safe, ethical training practices.

📈 Career Progression

Typical Career Path

Entry Point From:

  • Senior Penetration Tester / Red Team Operator
  • Security Consultant (Offensive focus)
  • Security Researcher / Vulnerability Researcher

Advancement To:

  • Lead/Principal Offensive Security Instructor
  • Red Team Lead / Director of Adversary Emulation
  • Head of Security Training & Enablement
  • Principal Security Architect (Offensive specialization)

Lateral Moves:

  • Curriculum Developer / Learning Experience Designer
  • Security Product Evangelist / Technical Trainer
  • Threat Intelligence Analyst (adversary simulation focus)

Core Responsibilities

Primary Functions

  • Design and deliver instructor-led and virtual instructor-led courses in offensive security topics (e.g., network and web penetration testing, Active Directory attacks, exploit development, post-exploitation, and adversary emulation) tailored to audience skill levels from entry to advanced.
  • Develop complete course curricula, learning objectives, slide decks, instructor guides, student handouts, and assessment rubrics that align with industry standards and certification requirements.
  • Create, configure, and maintain scalable, repeatable hands-on lab environments (on-premise VMs, cloud labs, or hybrid infrastructure) that simulate realistic enterprise architectures and adversary tactics.
  • Lead live offensive demonstrations and guided exploit walkthroughs in class, safely showing effective techniques while explaining mitigation and detection implications.
  • Build and maintain reusable exercise packages and challenge labs (capture-the-flag style, scenario-based drills) including automated reset/clean-up and scoring logic.
  • Mentor and coach students during practical exercises, providing targeted feedback on technique, methodology, tool use, and post-exploitation tradeoffs.
  • Perform hands-on vulnerability assessments and proof-of-concept exploit development to create new lab content, ensuring exercises reflect current threat actor techniques and zero-day themes where appropriate.
  • Operate and instruct with common offensive frameworks and tooling (e.g., Cobalt Strike, Metasploit, Empire, BloodHound) while emphasizing safe, legal, and ethical use.
  • Teach secure and responsible red teaming practices including rules of engagement, scope definition, blast radius control, and escalation/response coordination with blue teams.
  • Evaluate student performance using objective criteria, produce grading reports, and certify student competency against course learning outcomes.
  • Collaborate with sales and client-facing teams to scope customer engagements, propose training solutions, and customize course content for specific organizational environments and threat models.
  • Create and maintain up-to-date training documentation, lab walkthroughs, step-by-step exercises, and post-course learning resources such as cheat sheets and video recaps.
  • Conduct train-the-trainer sessions to scale instructional capacity, mentor junior instructors, and ensure consistent delivery quality across multiple trainers and cohorts.
  • Integrate detection, logging, and telemetry considerations into offensive training by demonstrating how attacks appear in SIEMs, EDRs, and network monitoring tools.
  • Measure training impact by collecting metrics (pre/post assessments, satisfaction surveys, skills retention) and iterate on course materials to improve learning outcomes.
  • Ensure all course activities comply with legal, regulatory, and contractual constraints; implement safety controls and exercise kill-switch procedures for live offensive labs.
  • Research emerging offensive techniques, publish internal advisories or public papers where appropriate, and incorporate findings into lessons and lab scenarios.
  • Support certification exam proctoring and manage certification track logistics, including prerequisites, exam content alignment, and re-certification requirements.
  • Lead simulated adversary campaigns (red team engagements) as part of advanced training packages, coordinating with blue teams for purple team exercises and after-action reviews.
  • Troubleshoot student and lab environment issues during delivery to minimize downtime and keep cohorts on schedule.
  • Contribute to productization of course content (on-demand labs, recorded modules, and certification tracks) and advise on platform choices for learning management systems (LMS) and lab orchestration.
  • Participate in hiring, interviewing, and onboarding new instructors; provide feedback and training to raise instructional quality and technical standards.

Secondary Functions

  • Assist marketing and pre-sales teams with technical content for proposals, demo scripts, and customer briefings to secure training and engagement contracts.
  • Support research & development initiatives by prototyping offensive toolchains, test harnesses, and lab automation used to scale training and red team operations.
  • Maintain an inventory of lab images, tooling licenses, and cloud resources; manage cost optimization and access control for training infrastructure.
  • Attend conferences, deliver public talks or workshops, and represent the organization in community outreach to attract talent and promote training offerings.
  • Contribute to open-source training projects, community CTFs, and knowledge-sharing initiatives to strengthen employer brand and recruit top talent.
  • Provide post-course follow-up: office hours, remediation sessions, and cohort-specific improvement plans based on assessments.

Required Skills & Competencies

Hard Skills (Technical)

  • Hands-on penetration testing skills across web applications, APIs, networks, and cloud environments (AWS/Azure/GCP), with ability to craft detailed lab exercises and real-world scenarios.
  • Strong experience with Active Directory attack chains (Kerberos abuse, AD privilege escalation, ACL abuse, Kerberoasting, DCSync, Silver/Tin/Golden Tickets).
  • Proficiency in exploit development and vulnerability research including memory corruption, buffer overflows, and basic reverse engineering (IDA/Ghidra).
  • Skilled in scripting and automation for labs and tooling in Python, PowerShell, Bash, and familiarity with automation frameworks (Ansible, Terraform for lab provisioning).
  • Practical experience with red team and adversary emulation tools such as Cobalt Strike, Metasploit, Empire, BloodHound, and common post-exploitation toolsets.
  • Ability to design and instrument labs that integrate SIEM/EDR telemetry and show offensive techniques’ observable artifacts (Splunk, Elastic, Sysmon, Windows event logging).
  • Knowledge of secure coding vulnerabilities and exploitation techniques for modern web stacks (SQLi, XSS, SSRF, deserialization, authentication flaws).
  • Experience delivering hands-on reverse engineering, malware analysis fundamentals, and unpacking obfuscated code in a classroom setting.
  • Familiarity with cloud-native attack surfaces including container escapes, misconfigured IAM, serverless weaknesses, and pipeline compromise techniques.
  • Knowledge of network exploitation, pivoting, tunneling, and defensive countermeasures (routing, VLANs, firewalls, SMB, AD over LDAP).
  • Experience building reproducible, resettable lab environments using virtualization (VMware, VirtualBox), containers (Docker), or cloud lab platforms.
  • Comfortable performing threat modeling and converting TTPs (tactics, techniques, procedures) into teachable exercises aligned to MITRE ATT&CK.
  • Experience with assessment authoring, exam proctoring, and creating objective-based scoring systems for practical red-team exercises.
  • Familiarity with common continuous integration/deployment security issues and supply-chain attack vectors to create realistic enterprise scenarios.
  • Knowledge of legal, compliance, and ethics frameworks relevant to offensive operations, including how to apply rules of engagement and escalation procedures.

Soft Skills

  • Exceptional communicator with experience delivering technical content to diverse audiences (executives, blue teamers, developers, operators).
  • Strong classroom management and facilitation skills to keep hands-on labs on schedule and students engaged.
  • Empathetic coaching and mentoring style to rapidly upskill students and provide constructive, actionable feedback.
  • Clear instructional design thinking: ability to break complex offensive techniques into progressive learning chunks.
  • Creative problem-solver who adapts exercises in real-time when labs or student comprehension diverge from plan.
  • Collaborative mindset to work with sales, product, and enterprise security teams to align training to business needs.
  • Strong attention to detail for lab reproducibility, documentation accuracy, and grading fairness.
  • Time management and organization skills to manage multiple cohorts, content updates, and travel commitments.
  • Professionalism and integrity to handle sensitive client environments and confidential red-team engagement findings.
  • Resilience and continuous learning orientation; stays current with threat research and iterates on course material.

Education & Experience

Educational Background

Minimum Education:

  • Bachelor's degree in Computer Science, Cybersecurity, Computer Engineering, Information Systems, or equivalent practical experience.

Preferred Education:

  • Master’s degree in Cybersecurity, Information Assurance, or related technical discipline.
  • Professional teaching, instructional design certificate, or adult learning coursework is a plus.

Relevant Fields of Study:

  • Computer Science
  • Cybersecurity / Information Security
  • Computer Engineering
  • Network Engineering
  • Information Assurance

Experience Requirements

Typical Experience Range:

  • 3–10 years in offensive security roles (penetration testing, red teaming, vulnerability research) with at least 1–3 years of formal training or mentoring experience.

Preferred:

  • 5+ years conducting enterprise penetration tests and red team exercises, plus 2+ years as a public-facing instructor or curriculum developer.
  • Recognized industry certifications such as OSCP, OSCE, GIAC GPEN/GCWN/GREM, SANS instructor credentials, CISSP, or equivalent demonstrable accomplishments.
  • Experience operating in enterprise, cloud, and government environments and comfortable obtaining/working within required security clearances if needed.
  • Prior experience creating and maintaining lab infrastructure and learning platforms (LMS, lab orchestration) and contributing to training product roadmaps.
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