About The Role

Do you love technology and thrive on helping others master it? Pluralsight’s Instructor-Led Training (ILT) team is seeking exceptional Independent Contract Technical Instructors to deliver engaging, high-impact training experiences for Fortune 500 clients.This opportunity allows you to lead live, instructor-led training sessions both in-person and virtually, empowering software developers to deepen their expertise in today’s most in-demand technologies. Pluralsight offers many ILT solutions including: short webinars, hackathons, 1-5 day classes, immersive academies, and blended learning academies. With topics that range from Generative AI to Cloud, DevOps to Data Science, and many more. You will guide learners through hands-on, real-world instruction that drives immediate impact.With flexible scheduling, competitive daily rates, and the ability to work from anywhere, this role is ideal for experienced technologists who are passionate about sharing knowledge and elevating teams.

Who you're committed to being

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

What you'll do

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

Experience you'll bring

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5+ years of hands-on professional experience in cybersecurity (e.g., Incident Response, SOC/Threat Hunting, Penetration Testing, or Security Engineering).
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2+ years of experience facilitating technical training, hosting CTFs, or leading incident response tabletop exercises.
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Deep expertise in one or more of the following areas

Tabletop Exercise (TTX) Design & Executive/Technical Facilitation

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CTF Challenge Development (Web Security, Forensics, Reverse Engineering, Binary Exploitation)
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Threat Frameworks (MITRE ATT&CK, NIST IR, OWASP Top 10)
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Incident Response Playbooks, Workflows, & After-Action Reporting (AAR)

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Offensive/Defensive Tooling & Scripting (Python, Bash, Wireshark, Splunk, Burp Suite, Metasploit)
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Cloud & Infrastructure Security Sandboxing (Docker, CTFd, Cloud Environments)
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Strong presentation skills with the ability to engage both executive leadership and technical engineering teams.
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Experience delivering security-focused workshops virtually and/or in person to enterprise clients is highly preferred.

Requirements

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