ciso-advisor

SKILL.md

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 ID Threat Asset SLE ARO ALE Mitigation Cost ROI Priority
R-001 Data breach (customer PII) Customer database $2.5M 0.15 $375K $120K/yr 3.1x Critical
R-002 Ransomware Production systems $1.8M 0.10 $180K $80K/yr 2.3x High
R-003 Insider threat Source code $500K 0.05 $25K $40K/yr 0.6x Medium
R-004 DDoS Customer-facing app $200K 0.20 $40K $30K/yr 1.3x Medium
R-005 Third-party breach Vendor with PII access $1.2M 0.08 $96K $25K/yr 3.8x High

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 Component Description Typical Range
Direct costs Forensics, remediation, legal $100K-$500K
Regulatory fines GDPR: up to 4% revenue; HIPAA: $100-$50K per record Varies widely
Notification costs $5-$50 per affected individual Scale with records
Business interruption Lost revenue during downtime Hours x hourly revenue
Reputation damage Customer churn, brand impact 2-5% annual revenue
Legal liability Lawsuits, 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

Framework Timeline Cost Best For Customer Requirement
SOC 2 Type I 3-6 months $50-100K B2B SaaS selling to US companies Most common ask
SOC 2 Type II 6-12 months $80-150K Sustained enterprise sales Required for large deals
ISO 27001 9-15 months $100-200K European market, global companies EU enterprise standard
HIPAA 6-12 months $80-200K Healthcare data handling Healthcare vertical
GDPR 3-6 months $30-80K Any company with EU users Legal requirement
PCI DSS 6-12 months $100-300K Payment card processing Payment requirement
FedRAMP 12-24 months $500K-2M US federal government sales Government requirement

Framework Overlap Matrix

Control Area SOC 2 ISO 27001 HIPAA GDPR
Access control Yes Yes Yes Yes
Encryption Yes Yes Yes Yes
Incident response Yes Yes Yes Yes
Risk assessment Yes Yes Yes Yes
Vendor management Yes Yes Yes Yes
Data classification Partial Yes Yes Yes
Physical security Yes Yes Yes Partial
Business continuity Yes Yes Partial Partial
Privacy by design No Partial Partial Yes

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

Level Description Key Controls Timeline
0: Ad-hoc No formal security architecture -- Current state for most startups
1: Identity MFA everywhere, SSO, role-based access IAM + MFA + SSO Months 1-3
2: Network Network segmentation, VPN/ZTNA Micro-segmentation, ZTNA Months 3-6
3: Data Data classification, encryption at rest/transit, DLP Encryption + classification Months 6-12
4: Monitoring SIEM, logging, anomaly detection Centralized logging + alerting Months 9-15
5: Automated Automated response, continuous verification SOAR + automated remediation Months 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

Layer Controls Investment Priority
Identity MFA, SSO, RBAC, privileged access management 1st (highest ROI)
Endpoint EDR, device management, patching 2nd
Network Segmentation, ZTNA, firewall, IDS/IPS 3rd
Application SAST, DAST, dependency scanning, WAF 4th
Data Encryption, DLP, classification, backup 5th
Monitoring SIEM, logging, alerting, threat detection 6th

Incident Response Protocol

Severity Classification

Severity Definition Response Time Notification
P0: Critical Active breach, data exfiltration, ransomware Immediate (< 15 min) CEO + Legal + Board
P1: High Vulnerability being exploited, service down < 1 hour CTO + CEO
P2: Medium Vulnerability discovered, suspicious activity < 4 hours CTO + Security team
P3: Low Policy violation, minor misconfiguration < 24 hours Security 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

Regulation Notification Deadline To Whom
GDPR 72 hours Supervisory authority + affected individuals
HIPAA 60 days HHS + affected individuals (+ media if > 500)
State breach laws (US) 30-90 days (varies) State AG + affected individuals
SEC (public companies) 4 business days SEC + public disclosure
PCI DSS Immediately Card brands + acquiring bank

Vendor Security Assessment

Vendor Tiering

Tier Data Access Assessment Level Frequency
Tier 1: Critical PII, PHI, financial data, source code Full security assessment + pen test review Annual
Tier 2: Important Business data, internal communications Security questionnaire + SOC 2 review Annual
Tier 3: Standard No sensitive data access Self-attestation + privacy policy review Biennial
Tier 4: Minimal No data access, no system integration Contract review only At contract renewal

Vendor Assessment Checklist (Tier 1)

Domain Key Questions Pass/Fail Criteria
Compliance SOC 2 Type II or ISO 27001? Must have at least one
Encryption Data encrypted at rest and in transit? AES-256 + TLS 1.2+
Access MFA enforced? RBAC implemented? Both required
Incident response Documented IR plan? Notification timeline? Must have plan + 24hr notification
Business continuity DR plan tested? RTO/RPO defined? Must be tested within 12 months
Data handling Data classification? Retention policy? Must have both
Subprocessors Who else handles our data? Must disclose all

Security Metrics Dashboard

Board-Level Metrics (Quarterly)

Metric Target Red Flag Board 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 status All current Any lapsed "All certifications active" or "Gap in X"
Critical vulnerabilities open 0 Any > 30 days "Zero unpatched critical vulnerabilities"

Operational Metrics (Monthly)

Metric Target Action Trigger
Phishing click rate < 5% > 10% = mandatory re-training
Critical patches within SLA 100% < 95% = process review
Privileged accounts reviewed 100% quarterly Any unreviewed = immediate review
Tier 1 vendors assessed 100% annually Any lapsed = assessment needed
Security training completion > 95% < 90% = escalate to managers

Security Budget Framework

Budget as Percentage of Revenue/IT Spend

Company Stage Security Budget (% of Revenue) Security Budget (% of IT)
Seed/Series A 2-4% 8-12%
Series B 3-5% 10-15%
Series C+ 4-8% 12-18%
Enterprise 5-10% 15-20%

Budget Allocation by Category

Category % of Security Budget Examples
People 40-50% Security team salaries, training
Tools 25-35% SIEM, EDR, IAM, vulnerability scanner
Compliance 10-15% Auditors, certifications, legal
Testing 5-10% Pen testing, red team, bug bounty
Incident response 5% 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 blocked CRO (cro-advisor) Complete security questionnaires, unblock deals
New product features CTO + CPO (cto-advisor, cpo-advisor) Threat modeling, security review
Compliance budget CFO (cfo-advisor) Size program against quantified risk exposure
Vendor contracts COO (coo-advisor) Security SLAs, right-to-audit clauses
M&A due diligence CEO + CFO Target security posture assessment
Incident occurs CEO + Legal Response coordination, regulatory notification
Board reporting CEO (ceo-advisor) Translate risk into business language
Hiring security team CHRO (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

Request Deliverable
"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
Weekly Installs
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