Tabletop Exercise Specialist - Cybersecurity Focus

resilience

United States

On-site

USD 100,000 - 135,000

Full time

6 days ago

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Benefits offered by this job

Flexible work schedules

Paid healthcare for employees

401k/Pension

Family paid leave

Flexible paid time off

Employee referral bonus

Accommodations and Accessibility

Job summary

Resilience is seeking a Tabletop Exercise (TTX) Specialist to design, build, and facilitate immersive cyber incident simulations for mid-to-large enterprises. You will test IRPs, DRPs, and BCPs, guiding executive teams through crisis scenarios and delivering strategic recommendations.

You will partner with client engagement teams, lead cross-functional sessions, and contribute to proprietary TTX frameworks while traveling up to 25% across the US and Europe.

Qualifications

3-5 years of proven experience designing and facilitating cybersecurity incident response TTXs, IRPs, DRPs, and BCPs for enterprise clients.
Mastery in facilitating crisis simulations for cross-functional enterprise stakeholders, including non-technical executives.
Bachelor's degree in Cybersecurity, Computer Science, IT, or related field (or equivalent).
Strong knowledge of major US and European cybersecurity/privacy regulations impacting incident response governance.
Strong project management skills to handle multiple client engagements and deadlines.
Willingness to travel up to 25% across the US and Europe.

Responsibilities

Design and tailor realistic TTX scenarios auditing client IRPs and identifying coverage gaps.
Lead virtual and in-person TTX sessions with C‑Suite, Legal, PR, and HR.
Deliver After‑Action Reports with lessons learned and actionable security recommendations.
Refine and scale Resilience's TTX frameworks as client portfolio grows globally.

Skills

TTX design

C-suite facilitation

Project management

Regulatory knowledge

Travel readiness

Crisis simulations

Education

Bachelor's in Cybersecurity or related field

Equivalent practical experience

Tools

TTX platforms

Job description

About Us

At Resilience, we're creating a new category that integrates cybersecurity, cyber insurance, and cyber risk management. Founded in 2016 by experts from across the highest tiers of the US military and intelligence communities - and built by prominent leaders and innovators from the insurance, technology, and cybersecurity industries - Resilience is rewriting the rules of how cyber risk is assessed, measured, and managed.

Our integrated cyber risk solutions connect risk quantification software, cybersecurity experts, and A+ rated cyber insurance, all purpose-built for middle and large organizations. We are a cybersecurity company, a Cyber and Tech E&O-focused MGA, a fintech startup, and a data science powerhouse, all purposefully built into one.

Resilience is proud to be backed by leading technology investment firms, including General Catalyst, Lightspeed Venture Partners, Intact Ventures, Founders Fund, CRV, and Shield Capital.

The Hook: Why this role matters now

Step into a high-visibility, client-facing role to drive real-world cyber resilience for middle to large enterprises with annual revenues ranging from $100M to $10B. Reporting to the Director of Security and Risk Services, as a Tabletop Exercise (TTX) Specialist, you won't just run routine drills; you will take complete ownership of designing, building, and facilitating immersive, crisis-level cyber incident simulations. You will serve as the trusted advisor who tests client Incident Response Plans (IRPs), Disaster Recovery Plans (DRPs), and Business Continuity Plans (BCPs), ensuring executive teams are battle-tested before a real threat strikes.

The Mission: What you will achieve in the first 6 months

In your first six months, you will take full accountability for building, tailoring, and facilitating realistic TTX scenarios that test our clients' operational and strategic cyber readiness:

Scenario Design & Engineering: Partner with Resilience Customer Engagement teams to audit client Incident Response Plans, identify critical coverage gaps, and author tailored exercise guides, facilitator scripts, and evaluation metrics mapped to each client's industry and regulatory requirements.
Executive & C‑Suite Facilitation: Confidently lead virtual and in-person TTX sessions, guiding cross-functional stakeholders-including non-technical executive leadership (C‑Suite, Legal, PR, and HR)-through complex decisions during simulated ransomware attacks, data breaches, and systemic security events.
Post‑TTX Analysis & Actionable Guidance: Conduct debriefing sessions and deliver comprehensive After‑Action Reports (AARs) summarizing lessons learned, regulatory decision‑making nuances, and actionable security recommendations.
Methodology Scaling: Contribute to refining Resilience's proprietary TTX frameworks, methodologies, and best practices as our client portfolio grows globally.

The Toolkit: Technical skills vs. "nice-to-haves"

Core Requirements:

3-5 years of proven experience designing and facilitating cybersecurity incident response TTXs, IRPs, DRPs, and BCPs for enterprise clients.
Demonstrated mastery in facilitating crisis simulations for cross-functional enterprise stakeholders, specifically non-technical C‑Suite executives, Legal, PR, and HR leaders.
Bachelor's degree in Cybersecurity, Computer Science, Information Technology, or a related field (or equivalent practical experience).
Strong working knowledge of major US and European cybersecurity and privacy regulations (GDPR, NIS2, CCPA, SEC cyber disclosure rules) and their impact on incident response governance.
Strong project management skills to handle multiple client engagements, coordinate enterprise schedules, and meet strict deadlines.
Willingness to travel up to 25% across the US and Europe.

Nice-to-Haves:

Relevant industry certifications (e.g., CISSP, CISM
Hands‑on proficiency with specialized TTX simulation platforms and software.

The Culture: How we work

We move fast, operate with zero ego, and embrace a bias to action. We are guided strongly by our four core values: transparency, excellence, grit, and humility. You will thrive in an exciting, collaborative startup culture alongside top-tier cybersecurity experts, maintaining a constructive learning environment for clients under pressure.

The Benefits: Standardized perks

You will work alongside prominent leaders and innovators from the insurance, technology, and cybersecurity industries, as well as experts from the highest tiers of the US military and intelligence communities.

Compensation range $100,000 - $135,000 USD

What Resilience Offers You