Cybersecurity, Incident Response & Hands-On Training Contract IT Instructor (Onsite and virtual live classes) (copy)

DevelopIntelligence; United States; Hybrid; USD 148,000 - 221,000; Part time

Job summary

Pluralsight is seeking Independent Contract Cybersecurity Instructors to deliver live, instructor-led sessions for Fortune 500 clients. You’ll run both virtual and in-person classes, craft realistic threat scenarios, and lead tabletop exercises and CTF events to strengthen client security postures.

You’ll stay current on MITRE ATT&CK, NIST IR, and OWASP Top 10 while mentoring teams and communicating with Pluralsight project managers to ensure high-impact outcomes.

Qualifications

• 5+ years hands-on cybersecurity experience (IR, SOC/Threat Hunting, Penetration Testing, or Security Engineering).
• 2+ years facilitating technical training, hosting CTFs, or leading IR tabletop exercises.
• Experience delivering instructor-led security training to enterprise clients.

Responsibilities

• Deliver live instructor-led cybersecurity training, including TTX and CTF for enterprise clients (virtual and onsite).
• Design industry-tailored threat scenarios and set up vulnerable labs or sandboxes.
• Facilitate debriefs and decision-making workflows with defensive remediation focus.
• Stay current on threat landscapes and industry security standards.
• Represent Pluralsight professionally while creating engaging learning environments.
• Communicate with project managers and manage class opportunities via the instructor portal.

Skills

Incident Response

Tabletop Exercise Design

CTF Challenge Development

MITRE ATT&CK

Public Speaking

Education

Bachelor’s degree in Cybersecurity

Cybersecurity certifications (CISSP, CISA, OSCP)

Tools

Python

Bash

Wireshark

Splunk

Burp Suite

Metasploit

CTFd

Docker

Job description

Position Title: Contract Instructor - Cybersecurity, Incident Response & Hands-On Training

Area: USA, APAC, EMEA, LATAM

Location/Work type: Remote: Virtual and in-person classes

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, and 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.

Experience you’ll bring:

• 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.

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, and 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.

Physical Requirements:

This role is primarily performed in an office or home office setting and involves standard computer-based work.

EEOC & Accommodations Statement:

Pluralsight is an equal opportunity employer. We evaluate qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, age, or veteran status. We also consider qualified applicants with criminal histories, consistent with EEOC guidelines and local laws.

If you need an accommodation to apply, interview, or perform essential job functions, please visit the bottom of our website to learn how to request an accommodation. Learn more about our commitment to diversity, equity, inclusion, and belonging in our DEIB Report.