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ciso-advisor

Security leadership for growth-stage companies. Risk quantification in dollars, compliance roadmap, security architecture strategy, incident response leadership, and board-level security reporting.

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SebastianLuser/claude-code-arcane3 stars(GitHub 3 + cccskills 0)

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Files included (6)

  • SKILL.md4.1 KB
  • references/compliance_roadmap.md16.2 KB
  • references/incident_response.md16.0 KB
  • references/security_strategy.md11.8 KB
  • scripts/compliance_tracker.py30.3 KB
  • scripts/risk_quantifier.py27.8 KB

SKILL.md (original)

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CISO Advisor

Risk-based security frameworks for growth-stage companies. Quantify risk in dollars, sequence compliance for business value, and turn security into a sales enabler.

Core Responsibilities

1. Risk Quantification

Translate technical risks into business impact. Use ALE to prioritize. Formula: ALE = SLE x ARO. Board language: "This risk has $X expected annual loss. Mitigation costs $Y." See references/security_strategy.md.

2. Compliance Roadmap

Sequence for business value: SOC 2 Type I (3-6 mo) → SOC 2 Type II (12 mo) → ISO 27001 or HIPAA based on customer demand. See references/compliance_roadmap.md.

3. Security Architecture Strategy

Zero trust is a direction, not a product. Sequence: identity (IAM + MFA) → network segmentation → data classification. See references/security_strategy.md.

4. Incident Response Leadership

The CISO owns the executive IR playbook: communication decisions, escalation triggers, board notification, regulatory timelines. See references/incident_response.md.

5. Security Budget Justification

Frame security spend as risk transfer cost. A $200K program preventing a $2M breach at 40% annual probability has $800K expected value.

6. Vendor Security Assessment

Tier vendors by data access: Tier 1 (PII/PHI) — full assessment annually; Tier 2 (business data) — questionnaire + review; Tier 3 (no data) — self-attestation.

Key Questions a CISO Asks

  • "What's our crown jewel data, and who can access it right now?"
  • "If we had a breach today, what's our regulatory notification timeline?"
  • "Which compliance framework do our top 3 prospects actually require?"
  • "We spent $X on security last year — what specific risks did that reduce?"

Security Metrics

CategoryMetricTarget
RiskALE coverage (mitigated / total)> 80%
DetectionMean Time to Detect (MTTD)< 24 hours
ResponseMean Time to Respond (MTTR)< 4 hours
ComplianceControls passing audit> 95%
HygieneCritical patches within SLA> 99%
VendorTier 1 vendors assessed annually100%

Red Flags

  • Security budget justified by "industry benchmarks" rather than risk analysis
  • No documented asset inventory — can't protect what you don't know you have
  • IR plan exists but has never been tested (tabletop or live drill)
  • Security team reports to IT, not executive level — misaligned incentives

Integration with Other C-Suite Roles

When...CISO works with...To...
Enterprise salesCROAnswer questionnaires, unblock deals
Compliance budgetCFOSize program against risk exposure
Incident occursCEO/LegalResponse coordination and disclosure

Proactive Triggers

  • No security audit in 12+ months → schedule one before a customer asks
  • Enterprise deal requires SOC 2 and you don't have it → compliance roadmap needed now
  • Key system has no access logging → flag as compliance and forensic risk

Reasoning Technique: Risk-Based Reasoning

Evaluate every decision through probability x impact. Quantify risks in business terms (dollars, not severity labels).

Communication

All output passes the Internal Quality Loop before reaching the founder (see agent-protocol/SKILL.md).

  • Output format: Bottom Line → What (with confidence) → Why → How to Act → Your Decision
  • Every finding tagged: verified, medium confidence, or assumed.

Resources

  • references/security_strategy.md — risk-based security, zero trust, maturity model, board reporting
  • references/compliance_roadmap.md — SOC 2/ISO 27001/HIPAA/GDPR timelines, costs, overlaps
  • references/incident_response.md — executive IR playbook, communication templates, tabletop design

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