Claude-Skills ciso-advisor

install
source · Clone the upstream repo
git clone https://github.com/borghei/Claude-Skills
Claude Code · Install into ~/.claude/skills/
T=$(mktemp -d) && git clone --depth=1 https://github.com/borghei/Claude-Skills "$T" && mkdir -p ~/.claude/skills && cp -r "$T/c-level-advisor/ciso-advisor" ~/.claude/skills/borghei-claude-skills-ciso-advisor && rm -rf "$T"
manifest: c-level-advisor/ciso-advisor/SKILL.md
source content

CISO Advisor

Risk-based security frameworks for growth-stage companies. Quantify risk in dollars, sequence compliance for maximum business value, build defense-in-depth architecture, and turn security from a cost center into a sales enabler and competitive advantage.

Keywords

CISO, security strategy, risk quantification, ALE, SLE, ARO, security posture, compliance roadmap, SOC 2, ISO 27001, HIPAA, GDPR, zero trust, defense in depth, incident response, board security reporting, vendor assessment, security budget, cyber risk, program maturity, penetration testing, vulnerability management, data classification, threat modeling, security awareness, phishing, MFA, IAM


Risk Quantification Framework

Every security investment must be justified in business terms. "We need better security" is not a business case. "$800K expected annual loss from this unmitigated risk" is.

Core Formula

ALE = SLE x ARO

ALE  = Annual Loss Expectancy (expected cost per year)
SLE  = Single Loss Expectancy (cost if the event occurs once)
ARO  = Annual Rate of Occurrence (probability of occurrence per year)

Risk Register Template

Risk IDThreatAssetSLEAROALEMitigation CostROIPriority
R-001Data breach (customer PII)Customer database$2.5M0.15$375K$120K/yr3.1xCritical
R-002RansomwareProduction systems$1.8M0.10$180K$80K/yr2.3xHigh
R-003Insider threatSource code$500K0.05$25K$40K/yr0.6xMedium
R-004DDoSCustomer-facing app$200K0.20$40K$30K/yr1.3xMedium
R-005Third-party breachVendor with PII access$1.2M0.08$96K$25K/yr3.8xHigh

Risk Prioritization Decision Tree

START: New risk identified
  |
  v
[Calculate ALE]
  |
  +-- ALE > $200K/yr --> CRITICAL: Board-level reporting, immediate mitigation
  |
  +-- ALE $50K-$200K --> HIGH: Quarterly review, funded mitigation plan
  |
  +-- ALE $10K-$50K --> MEDIUM: Annual review, budget if ROI > 1.5x
  |
  +-- ALE < $10K --> LOW: Accept risk, document decision, monitor

SLE Component Breakdown

Cost ComponentDescriptionTypical Range
Direct costsForensics, remediation, legal$100K-$500K
Regulatory finesGDPR: up to 4% revenue; HIPAA: $100-$50K per recordVaries widely
Notification costs$5-$50 per affected individualScale with records
Business interruptionLost revenue during downtimeHours x hourly revenue
Reputation damageCustomer churn, brand impact2-5% annual revenue
Legal liabilityLawsuits, settlements$50K-$5M+

Compliance Roadmap

Sequencing for Maximum Business Value

Phase 1: Foundation (Months 1-3)
  Basic hygiene: MFA, endpoint protection, access controls, backups
  Cost: $20-50K   Impact: Blocks 80% of common attacks

Phase 2: SOC 2 Type I (Months 3-6)
  Policies, procedures, controls documentation
  Cost: $50-100K  Impact: Unlocks mid-market enterprise sales

Phase 3: SOC 2 Type II (Months 6-12)
  Sustained controls operation + audit
  Cost: $80-150K  Impact: Required by most enterprise buyers

Phase 4: Specialized (Months 12-18)
  ISO 27001, HIPAA, or GDPR based on market requirements
  Cost: $100-250K Impact: Market-specific requirement fulfillment

Compliance Framework Comparison

FrameworkTimelineCostBest ForCustomer Requirement
SOC 2 Type I3-6 months$50-100KB2B SaaS selling to US companiesMost common ask
SOC 2 Type II6-12 months$80-150KSustained enterprise salesRequired for large deals
ISO 270019-15 months$100-200KEuropean market, global companiesEU enterprise standard
HIPAA6-12 months$80-200KHealthcare data handlingHealthcare vertical
GDPR3-6 months$30-80KAny company with EU usersLegal requirement
PCI DSS6-12 months$100-300KPayment card processingPayment requirement
FedRAMP12-24 months$500K-2MUS federal government salesGovernment requirement

Framework Overlap Matrix

Control AreaSOC 2ISO 27001HIPAAGDPR
Access controlYesYesYesYes
EncryptionYesYesYesYes
Incident responseYesYesYesYes
Risk assessmentYesYesYesYes
Vendor managementYesYesYesYes
Data classificationPartialYesYesYes
Physical securityYesYesYesPartial
Business continuityYesYesPartialPartial
Privacy by designNoPartialPartialYes

Key insight: SOC 2 + ISO 27001 share approximately 70% of controls. Do SOC 2 first, then extend to ISO 27001 with ~30% incremental effort.


Security Architecture Strategy

Zero Trust Maturity Model

LevelDescriptionKey ControlsTimeline
0: Ad-hocNo formal security architecture--Current state for most startups
1: IdentityMFA everywhere, SSO, role-based accessIAM + MFA + SSOMonths 1-3
2: NetworkNetwork segmentation, VPN/ZTNAMicro-segmentation, ZTNAMonths 3-6
3: DataData classification, encryption at rest/transit, DLPEncryption + classificationMonths 6-12
4: MonitoringSIEM, logging, anomaly detectionCentralized logging + alertingMonths 9-15
5: AutomatedAutomated response, continuous verificationSOAR + automated remediationMonths 12-24

Security Architecture Decision Tree

START: New system or feature being designed
  |
  v
[Does it handle sensitive data?]
  |
  +-- YES --> [What classification level?]
  |            |
  |            +-- PII/PHI --> Full security review + threat model
  |            +-- Business-critical --> Standard security review
  |            +-- Internal --> Lightweight checklist
  |
  +-- NO  --> [Is it internet-facing?]
              |
              +-- YES --> Standard security review + pen test
              +-- NO  --> Security checklist only

Defense-in-Depth Layers

LayerControlsInvestment Priority
IdentityMFA, SSO, RBAC, privileged access management1st (highest ROI)
EndpointEDR, device management, patching2nd
NetworkSegmentation, ZTNA, firewall, IDS/IPS3rd
ApplicationSAST, DAST, dependency scanning, WAF4th
DataEncryption, DLP, classification, backup5th
MonitoringSIEM, logging, alerting, threat detection6th

Incident Response Protocol

Severity Classification

SeverityDefinitionResponse TimeNotification
P0: CriticalActive breach, data exfiltration, ransomwareImmediate (< 15 min)CEO + Legal + Board
P1: HighVulnerability being exploited, service down< 1 hourCTO + CEO
P2: MediumVulnerability discovered, suspicious activity< 4 hoursCTO + Security team
P3: LowPolicy violation, minor misconfiguration< 24 hoursSecurity team only

Incident Response Workflow

DETECT --> CONTAIN --> ERADICATE --> RECOVER --> LEARN

Phase 1: DETECT (Minutes)
  - Identify the scope and nature of the incident
  - Classify severity (P0-P3)
  - Activate response team based on severity

Phase 2: CONTAIN (Hours)
  - Isolate affected systems
  - Preserve evidence (forensic images)
  - Prevent lateral movement
  - Communicate to stakeholders per severity matrix

Phase 3: ERADICATE (Hours-Days)
  - Remove threat actor/malware
  - Patch vulnerability that enabled the incident
  - Verify eradication is complete

Phase 4: RECOVER (Days)
  - Restore from clean backups
  - Verify system integrity
  - Monitor for re-compromise
  - Return to normal operations

Phase 5: LEARN (Days-Weeks)
  - Root cause analysis (blameless)
  - Timeline reconstruction
  - Control gap identification
  - Remediation plan with owners and deadlines

Regulatory Notification Timelines

RegulationNotification DeadlineTo Whom
GDPR72 hoursSupervisory authority + affected individuals
HIPAA60 daysHHS + affected individuals (+ media if > 500)
State breach laws (US)30-90 days (varies)State AG + affected individuals
SEC (public companies)4 business daysSEC + public disclosure
PCI DSSImmediatelyCard brands + acquiring bank

Vendor Security Assessment

Vendor Tiering

TierData AccessAssessment LevelFrequency
Tier 1: CriticalPII, PHI, financial data, source codeFull security assessment + pen test reviewAnnual
Tier 2: ImportantBusiness data, internal communicationsSecurity questionnaire + SOC 2 reviewAnnual
Tier 3: StandardNo sensitive data accessSelf-attestation + privacy policy reviewBiennial
Tier 4: MinimalNo data access, no system integrationContract review onlyAt contract renewal

Vendor Assessment Checklist (Tier 1)

DomainKey QuestionsPass/Fail Criteria
ComplianceSOC 2 Type II or ISO 27001?Must have at least one
EncryptionData encrypted at rest and in transit?AES-256 + TLS 1.2+
AccessMFA enforced? RBAC implemented?Both required
Incident responseDocumented IR plan? Notification timeline?Must have plan + 24hr notification
Business continuityDR plan tested? RTO/RPO defined?Must be tested within 12 months
Data handlingData classification? Retention policy?Must have both
SubprocessorsWho else handles our data?Must disclose all

Security Metrics Dashboard

Board-Level Metrics (Quarterly)

MetricTargetRed FlagBoard Language
ALE coverage> 80%< 60%"$X of $Y total risk is mitigated"
Mean time to detect (MTTD)< 24 hours> 72 hours"We find threats within X hours"
Mean time to respond (MTTR)< 4 hours> 24 hours"We contain threats within X hours"
Compliance statusAll currentAny lapsed"All certifications active" or "Gap in X"
Critical vulnerabilities open0Any > 30 days"Zero unpatched critical vulnerabilities"

Operational Metrics (Monthly)

MetricTargetAction Trigger
Phishing click rate< 5%> 10% = mandatory re-training
Critical patches within SLA100%< 95% = process review
Privileged accounts reviewed100% quarterlyAny unreviewed = immediate review
Tier 1 vendors assessed100% annuallyAny lapsed = assessment needed
Security training completion> 95%< 90% = escalate to managers

Security Budget Framework

Budget as Percentage of Revenue/IT Spend

Company StageSecurity Budget (% of Revenue)Security Budget (% of IT)
Seed/Series A2-4%8-12%
Series B3-5%10-15%
Series C+4-8%12-18%
Enterprise5-10%15-20%

Budget Allocation by Category

Category% of Security BudgetExamples
People40-50%Security team salaries, training
Tools25-35%SIEM, EDR, IAM, vulnerability scanner
Compliance10-15%Auditors, certifications, legal
Testing5-10%Pen testing, red team, bug bounty
Incident response5%Retainer, insurance, forensics

Budget Justification Formula

For each security investment:

Investment ROI = (ALE_before - ALE_after) / Investment_cost

If ROI > 1.5x --> Strong business case, approve
If ROI 1.0-1.5x --> Moderate case, consider alternatives
If ROI < 1.0x --> Weak case, re-evaluate or accept the risk

Red Flags

  • Security budget justified by "industry benchmarks" instead of risk analysis -- budget will be wrong
  • Pursuing certifications before basic hygiene (MFA, patching, backups) -- checkbox without substance
  • No documented asset inventory -- protecting unknown assets is impossible
  • IR plan exists but never tested (no tabletop exercise) -- plan will fail when needed
  • Security team reports to IT, not executive level -- misaligned incentives, budget competition
  • Single vendor for identity + endpoint + email -- vendor compromise = total compromise
  • Security questionnaire backlog > 30 days -- silently losing enterprise deals
  • No security champion program in engineering -- security becomes a bottleneck
  • Pen test findings unresolved after 90 days -- testing without fixing is theater
  • No data classification scheme -- everything treated the same = nothing protected properly

Integration with C-Suite

When...CISO Works With...To...
Enterprise sales blockedCRO (
cro-advisor
)
Complete security questionnaires, unblock deals
New product featuresCTO + CPO (
cto-advisor
,
cpo-advisor
)
Threat modeling, security review
Compliance budgetCFO (
cfo-advisor
)
Size program against quantified risk exposure
Vendor contractsCOO (
coo-advisor
)
Security SLAs, right-to-audit clauses
M&A due diligenceCEO + CFOTarget security posture assessment
Incident occursCEO + LegalResponse coordination, regulatory notification
Board reportingCEO (
ceo-advisor
)
Translate risk into business language
Hiring security teamCHRO (
chro-advisor
)
Compensation, leveling, recruiting

Proactive Triggers

  • No security audit in 12+ months -- schedule before a customer or regulator asks
  • Enterprise deal requires SOC 2 but no certification exists -- compliance roadmap urgently needed
  • New market expansion planned -- check data residency, privacy requirements, local regulations
  • Key system has no access logging -- compliance gap and forensic blind spot
  • Vendor with access to sensitive data not assessed -- vendor risk assessment required
  • Critical vulnerability disclosed in a dependency -- patch assessment within 24 hours
  • Employee termination without access revocation SOP -- immediate security gap

Output Artifacts

RequestDeliverable
"Assess our security posture"Risk register with quantified ALE, prioritized by business impact
"We need SOC 2"Compliance roadmap: timeline, cost, effort, quick wins, vendor selection
"Prep for security audit"Gap analysis against target framework + remediation plan with owners
"We had an incident"IR coordination plan + communication templates + regulatory timeline
"Security board section"Risk posture summary, compliance status, incident report, budget ask
"Evaluate vendor security"Vendor tier assessment with risk scoring and contract recommendations
"Justify security budget"Risk-based budget proposal with ROI for each investment

Tool Reference

security_posture_scorer.py

Scores security posture across NIST CSF 2.0 functions (Govern, Identify, Protect, Detect, Respond, Recover) and CISA Zero Trust Maturity Model pillars (Identity, Devices, Networks, Applications, Data). Produces board-ready security health reports.

# Run with demo data (realistic Series B company)
python scripts/security_posture_scorer.py

# From JSON with control assessments (0-4 maturity per control)
python scripts/security_posture_scorer.py --input controls.json

# JSON output
python scripts/security_posture_scorer.py --json

risk_register_manager.py

Manages cyber risk register with ALE (SLE x ARO) calculations, mitigation ROI, and board-ready risk reports.

# Run with demo risk register
python scripts/risk_register_manager.py

# From JSON risk register
python scripts/risk_register_manager.py --input risks.json

# Sort by ROI (best investments first)
python scripts/risk_register_manager.py --sort-by roi

# JSON output
python scripts/risk_register_manager.py --json

compliance_tracker.py

Tracks progress across SOC 2 Type I/II, ISO 27001, HIPAA, and GDPR. Calculates gap analysis, framework overlaps, and effort estimates.

# Track SOC 2 readiness (default)
python scripts/compliance_tracker.py

# Track multiple frameworks
python scripts/compliance_tracker.py --frameworks soc2_type1 iso27001 gdpr

# List available frameworks
python scripts/compliance_tracker.py --list-frameworks

# From JSON
python scripts/compliance_tracker.py --input compliance.json

# JSON output
python scripts/compliance_tracker.py --json

Troubleshooting

ProblemLikely CauseFix
Security budget justified by "industry benchmarks" not risk dataNo risk quantification framework in placeImplement ALE-based risk register; justify every dollar against quantified risk reduction
Pursuing SOC 2 before basic hygiene (MFA, backups)Checkbox compliance without substancePhase 1 foundation first: MFA, endpoint protection, backups; then pursue certifications
Pen test findings unresolved after 90 daysTesting without fixing is theaterSet SLA: critical 7 days, high 30 days, medium 90 days; track in risk register
Security team reports to IT, not executive levelMisaligned incentives and budget competitionCISO should report to CEO or COO; separate budget from IT
Enterprise deals blocked by security questionnairesNo SOC 2 or questionnaire response backlog > 30 daysPrioritize SOC 2 Type I; create questionnaire response library; assign dedicated owner
Zero Trust initiative stalled at identity layerTrying to implement all pillars simultaneouslyFollow maturity model: Identity first (months 1-3), then Network, then Data

Success Criteria

  • Security posture score above 70/100 on NIST CSF assessment (measured annually via security_posture_scorer.py)
  • ALE coverage above 80% -- quantified risk exposure has funded mitigations (tracked in risk register)
  • Mean time to detect (MTTD) under 24 hours for all severity levels
  • Mean time to respond (MTTR) under 4 hours for P0/P1 incidents
  • Zero critical vulnerabilities open longer than 7 days (measured weekly)
  • SOC 2 Type II certification maintained current with zero control exceptions
  • Phishing click rate below 5% across quarterly simulation campaigns

Scope & Limitations

In Scope: Risk quantification (ALE/SLE/ARO), compliance roadmapping, Zero Trust maturity assessment, NIST CSF 2.0 scoring, incident response protocol, vendor security assessment, security budget justification, board-level security reporting.

Out of Scope: Penetration testing execution, malware analysis, SOC operations, firewall configuration, code review, forensic investigation execution, security tool procurement.

Limitations: Security posture scorer uses self-assessed maturity levels which may overstate actual capability. Risk register ALE calculations are estimates based on industry data -- actual losses vary significantly. Compliance tracker measures control implementation, not control effectiveness. Zero Trust scoring uses binary (implemented/not) which oversimplifies partial implementations.


Integration Points

SkillIntegration
cto-advisor
Security architecture reviews; threat modeling for new features
cfo-advisor
Security budget sizing against quantified risk; compliance costs
ceo-advisor
Board security reporting; incident communication to stakeholders
coo-advisor
Vendor security SLAs; right-to-audit contract clauses
cro-advisor
Security questionnaire response; SOC 2 as sales enabler
chro-advisor
Security team hiring; security awareness training programs
board-deck-builder
Risk/security section of board deck with posture score and compliance status
ra-qm-team
Extended compliance frameworks (ISO 13485, MDR, FDA, GDPR, NIS2, DORA)