Tabletop Exercise (TTX) Specialist - Cybersecurity Focus

About Us

At the company, 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.

The company 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 the company 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 the company’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 the company Offers You

Innovative company culture

Flexible work schedules

Family paid leave

Paid healthcare for employees

401k/Pension

Professional development & career advancements

Flexible paid time off

Employee referral bonus

Accommodations and Accessibility

We want to ensure you're able to perform as well as possible in your interview. As part of that, if you have any accessibility-related needs to ensure a comfortable visit, please let us know. We'll do our best to provide reasonable accommodations to suit your working style during your interview and if you join our team.

If you require a reasonable accommodation in completing this application, interviewing, completing any pre-employment testing, or otherwise participating in the employee selection process, please let your recruiter contact know.

Beware of Job Scams

The company is excited to welcome talented individuals to explore career opportunities with us. However, we urge you to stay vigilant against recruitment scams where fraudsters may impersonate our company. We will never ask for payments, conduct interviews via chat rooms, or contact candidates from personal email accounts. All job applications must be submitted through our official platform at greenhouse.io , and interviews will only take place via approved the company accounts. If you receive suspicious outreach or have concerns, please let your recruiter contact know. Thank you for helping us maintain a safe and secure recruitment process.