[Hiring] Cybersecurity Instructor @Pluralsight

Role Description

Do you love cybersecurity and thrive on helping organizations strengthen their security posture and build resilient defense teams? Pluralsight’s Instructor-Led Training (ILT) team is seeking exceptional Independent Contract Cybersecurity Instructors and Scenario Developers to deliver engaging, high-impact training experiences for Fortune 500 clients. This opportunity allows you to lead live, instructor-led sessions both in-person and virtually, empowering technical and leadership teams through interactive Tabletop Exercises (TTX) and competitive Capture the Flag (CTF) events. Pluralsight offers many ILT solutions including:

• Short workshops
• 1–5 day classes
• Immersive security academies
• Blended learning solutions

With topics ranging from incident response workflows to hands-on Red/Blue/Purple team exercises, you will guide learners through structured, real-world instruction that drives immediate security impact. With flexible scheduling, competitive daily rates, and the ability to work from anywhere, this role is ideal for experienced security professionals who are passionate about sharing knowledge and elevating teams.

Who you're committed to being:

• A passionate educator who believes cybersecurity learning should be practical, engaging, and transformational.
• A confident communicator who can bridge the gap between high-level incident response strategy and hands-on technical skill-building for diverse audiences.
• A continuous learner who stays current with emerging threats, evolving exploit mechanics, and modern security frameworks.
• A collaborative partner who works closely with client stakeholders and Pluralsight teams to evaluate security readiness and ensure exceptional delivery.
• A professional who demonstrates reliability, adaptability, and a strong commitment to learner and organizational success.

What you'll do:

• Deliver live instructor-led cybersecurity training, interactive Tabletop Exercises (TTX), and Capture the Flag (CTF) events (both virtual and onsite) for enterprise clients.
• Design industry-tailored threat scenarios, author CTF challenges, and set up vulnerable lab or sandbox environments.
• Facilitate decision-making workflows, post-exercise debriefs (hotwashes), and technical walkthroughs that reinforce defensive remediation strategies.
• Stay current on emerging threat landscapes, MITRE ATT&CK TTPs, and industry security standards.
• Represent Pluralsight professionally while creating an engaging, inclusive, and high-energy learning environment.
• Actively monitor our Instructor Portal to accept/decline class opportunities and communicate timely with Pluralsight project managers.

Qualifications

• 5+ years of hands-on professional experience in cybersecurity (e.g., Incident Response, SOC/Threat Hunting, Penetration Testing, or Security Engineering).
• 2+ years of experience facilitating technical training, hosting CTFs, or leading incident response tabletop exercises.
• Deep expertise in one or more of the following areas:
• Tabletop Exercise (TTX) Design & Executive/Technical Facilitation
• CTF Challenge Development (Web Security, Forensics, Reverse Engineering, Binary Exploitation)
• Threat Frameworks (MITRE ATT&CK, NIST IR, OWASP Top 10)
• Incident Response Playbooks, Workflows, & After-Action Reporting (AAR)
• Offensive/Defensive Tooling & Scripting (Python, Bash, Wireshark, Splunk, Burp Suite, Metasploit)
• Cloud & Infrastructure Security Sandboxing (Docker, CTFd, Cloud Environments)
• Strong presentation skills with the ability to engage both executive leadership and technical engineering teams.
• Experience delivering security-focused workshops virtually and/or in person to enterprise clients is highly preferred.

Requirements

• Minimum 5 years of hands-on cybersecurity experience.
• Minimum 2 years of instructional, training, or workshop facilitation experience.
• Ability to deliver training sessions virtually and travel onsite as needed.
• Strong verbal and written communication skills.
• Reliable high-speed internet and professional home office setup for virtual delivery.
• Legal authorization to work as an Independent Contractor.
• Bachelor’s degree in Cybersecurity, Computer Science, Information Technology, or related field preferred (or equivalent professional experience).
• Relevant cybersecurity certifications (e.g., CISSP, GCIH, OSCP, CEH, GRID, Security+) are a plus but not required.

Company Description

Pluralsight provides the only learning platform dedicated to accelerating the technology skills and capabilities of today’s tech workforce. Thousands of companies, government organizations and individuals around the world rely on Pluralsight to support critical technology skill development in areas that are crucial to innovation including:

• Artificial intelligence
• Cloud computing
• Cybersecurity
• Software development
• Machine learning

Pluralsight provides highly curated content developed by vetted technology experts, industry leading skill assessments, and hands-on, immersive learning experiences designed to help individuals skill-up faster.