Cybersecurity Tabletop Facilitator

Location: Denver Metro Based / Virtual Sessions

Job Type: W2 Part Time (OE friendly)

Pay: $40/hr and Bonus for well reviewed Tabletop Sessions up to $500 each session

About Tier 5

Tier 5 is redefining cybersecurity readiness through immersive, story-driven tabletop exercises. By blending technical expertise with engaging, themed experiences—including Dungeons & Dragons-style gameplay—we help clients prepare for real-world threats in memorable and impactful ways.

Position Summary

We’re seeking a dynamic Cybersecurity Tabletop Facilitator who thrives at the intersection of cybersecurity, storytelling, and role play. In this role, you’ll lead simulated incident response sessions modeled after Dungeons & Dragons adventures, guiding organizations through custom-built tabletop scenarios with narrative flair and technical accuracy.

Key Responsibilities

  • Facilitate 4 hour themed tabletop exercises for clients

  • Be available for scheduled events

  • Roleplay as a Dungeon Master-style narrator in scenarios (fantasy, spy, post-apocalyptic, cyberpunk, etc.)

  • Guide cross-functional teams through escalating cybersecurity incidents

  • Adapt storytelling based on participant choices and actions

  • Debrief teams and compile observations into post-mortem reports

  • Provide feedback on team decision-making, communication, and controls

  • Assist in refining existing tabletop content and developing new themes

  • Retaining Clients for future engagements and/or services

Required Skills & Experience

  • Experience running or participating in Dungeons & Dragons or other tabletop RPGs

  • Strong understanding of cybersecurity concepts: incident response, phishing, malware, ransomware, zero-day exploits, etc.

  • Excellent communication and facilitation skills

  • Comfort speaking to diverse groups (technical and non-technical)

  • Familiarity with Compliance Frameworks (NIST, ISO 27001, HIPAA, or SOC 2)

  • Ability to stay on-script while improvising within a scenario

  • Background in IT / IT Security

Bonus Points For

  • Prior experience as a vCISO, helpdesk, sys admin, SOC analyst, or tabletop facilitator

  • Public speaking or training experience

  • Voice acting, improv, or game design background

  • IT / Security Certifications

What You’ll Love

  • Flexible scheduling (virtual and in-person options)

  • Unique blend of storytelling, technology, and training

  • Branded templates, slides, and content provided

  • Great for cybersecurity pros with a creative streak

  • Over-employment Friendly, keep your regular employment

How to Apply

Send your resume and a brief pitch about your D&D or roleplaying experience to careers@tier5security.com. Bonus: Share a sample encounter or scenario idea!