claude-code-arcane 1.0.0

package/skills/ciso-advisor/SKILL.md

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+---
+name: ciso-advisor
+description: "Security leadership for growth-stage companies. Risk quantification in dollars, compliance roadmap, security architecture strategy, incident response leadership, and board-level security reporting."
+argument-hint: ""
+category: "clevel-advisors"
+user-invocable: true
+allowed-tools: Read, Glob, Grep, Bash
+---
+
+# 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
+
+| Category | Metric | Target |
+|----------|--------|--------|
+| Risk | ALE coverage (mitigated / total) | > 80% |
+| Detection | Mean Time to Detect (MTTD) | < 24 hours |
+| Response | Mean Time to Respond (MTTR) | < 4 hours |
+| Compliance | Controls passing audit | > 95% |
+| Hygiene | Critical patches within SLA | > 99% |
+| Vendor | Tier 1 vendors assessed annually | 100% |
+
+## 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 sales | CRO | Answer questionnaires, unblock deals |
+| Compliance budget | CFO | Size program against risk exposure |
+| Incident occurs | CEO/Legal | Response 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

package/skills/ciso-advisor/references/compliance_roadmap.md

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+# Compliance Roadmap Reference
+
+## Decision Framework: Which Framework First?
+
+**Start here — who are your customers?**
+
+```
+Enterprise SaaS (B2B, US market)  →  SOC 2 Type II first
+Healthcare / health data           →  HIPAA + SOC 2 together
+EU customers or EU-resident data   →  GDPR (non-optional if applicable)
+EU enterprise sales                →  ISO 27001 + GDPR
+Government / defense               →  FedRAMP / CMMC (separate scope)
+All of the above (Series B+)       →  Multi-framework efficiency approach
+```
+
+**The sequencing principle:** SOC 2 Type I is the fastest proof of intent (3–6 months). Type II is the credibility signal (12 months). Everything else builds on your control library.
+
+---
+
+## 1. SOC 2
+
+### What It Is
+SOC 2 is an attestation (not a certification) that your controls meet the AICPA Trust Service Criteria. An independent CPA firm audits your controls and issues a report.
+
+- **Type I:** Controls are suitably designed at a point in time (snapshot). Lower credibility but faster.
+- **Type II:** Controls operated effectively over a period of time (minimum 6 months). This is what enterprise buyers want.
+
+### Trust Service Criteria (TSC)
+You must include **Security** (CC). Others are optional:
+| Criteria | When to add |
+|---|---|
+| Security (CC) | Always required |
+| Availability | If uptime SLAs are contractual |
+| Confidentiality | If you process confidential third-party data |
+| Processing Integrity | If accuracy of processing is critical (fintech, data processing) |
+| Privacy | If you make privacy commitments beyond GDPR/CCPA scope |
+
+Most startups: **Security + Availability** is sufficient.
+
+### Timeline: SOC 2 Type I
+
+| Phase | Duration | Activities |
+|---|---|---|
+| Readiness assessment | 2–4 weeks | Gap analysis against CC criteria, identify control owners |
+| Policy documentation | 4–6 weeks | Write ~15–20 policies (acceptable use, access control, change management, etc.) |
+| Control implementation | 4–8 weeks | Deploy technical controls, fix gaps identified in readiness |
+| Evidence collection | 2–4 weeks | Screenshots, logs, configs — auditor will sample these |
+| Audit fieldwork | 2–4 weeks | CPA firm reviews evidence, interviews control owners |
+| Report issuance | 2–4 weeks | Report issued, reviewed, shared with customers |
+| **Total** | **3–6 months** | — |
+
+### Timeline: SOC 2 Type II (after Type I)
+
+| Phase | Duration | Notes |
+|---|---|---|
+| Observation period | 6–12 months | Controls must operate consistently — no exceptions |
+| Audit fieldwork | 4–6 weeks | Auditor samples evidence across full period |
+| Report issuance | 2–4 weeks | — |
+| **Total from Type I** | **9–18 months** | Faster if Type I was clean |
+
+### Cost Estimates
+
+| Item | SOC 2 Type I | SOC 2 Type II |
+|---|---|---|
+| Audit firm fees | $15,000–$35,000 | $25,000–$60,000 |
+| Compliance platform (Vanta, Drata, Secureframe) | $12,000–$30,000/yr | Same platform |
+| External counsel / vCISO | $10,000–$30,000 | $5,000–$15,000 maintenance |
+| Internal time (eng + ops) | 200–400 hours | 100–200 hours/yr |
+| **Total first year** | **$40,000–$100,000** | **+$30,000–$75,000** |
+
+**Cost optimization tips:**
+- Use a compliance platform (Vanta, Drata, Secureframe) — automated evidence collection halves audit cost
+- Choose a mid-tier audit firm; Big 4 is overkill for startups
+- Type I and Type II with same auditor = continuity discount
+
+### Common Failure Modes
+1. Controls documented but not operating (access reviews on paper only)
+2. Exceptions during observation period (one admin account without MFA = finding)
+3. No formal security awareness training (required for CC criteria)
+4. Change management not followed (no ticket for that production change)
+5. Vendor risk management missing (you must assess your critical vendors)
+
+---
+
+## 2. ISO 27001
+
+### What It Is
+ISO 27001 is an internationally recognized certification for an Information Security Management System (ISMS). Unlike SOC 2, it's a certification (pass/fail), not an attestation report. Issued by accredited certification bodies (BSI, Bureau Veritas, DNV, TÜV).
+
+**Why ISO 27001 over SOC 2:** EU enterprise buyers, government contracts, and global markets often prefer or require ISO 27001. It's geographically neutral.
+
+### Scope Decision
+ISO 27001 scope is flexible — you can certify a subset of the organization.
+- **Narrow scope:** The production environment only — fastest, cheapest
+- **Full scope:** Entire organization — most credibility, highest effort
+- **Recommended for startups:** Production environment + key business processes
+
+### Certification Timeline
+
+| Phase | Duration | Activities |
+|---|---|---|
+| Gap analysis | 2–4 weeks | Assess current state vs. 93 controls in Annex A |
+| ISMS design | 4–8 weeks | Scope, risk methodology, SoA (Statement of Applicability) |
+| Policy and procedure development | 6–10 weeks | Mandatory documents: risk treatment plan, asset register, ISMS policy |
+| Risk assessment | 4–6 weeks | Identify, analyze, evaluate risks; produce risk register |
+| Control implementation | 8–16 weeks | Implement gaps from risk assessment |
+| Internal audit | 2–4 weeks | First internal audit of ISMS |
+| Management review | 1–2 weeks | Leadership sign-off on ISMS |
+| Stage 1 audit (documentation) | 1–2 weeks | Certification body reviews docs and scope |
+| Stage 2 audit (implementation) | 1–2 weeks | Certification body verifies controls are operating |
+| Certification issued | 1–2 weeks | Certificate valid for 3 years with annual surveillance audits |
+| **Total** | **9–18 months** | — |
+
+### Cost Estimates
+
+| Item | Cost |
+|---|---|
+| Certification body fees (Stage 1 + Stage 2) | $15,000–$40,000 |
+| Annual surveillance audits | $8,000–$20,000/yr |
+| vCISO / consultant (if not in-house) | $30,000–$80,000 |
+| GRC platform | $10,000–$25,000/yr |
+| Internal time | 400–800 hours |
+| **Total first year** | **$55,000–$150,000** |
+
+### Mandatory ISO 27001:2022 Documents
+- ISMS scope document
+- Information security policy
+- Risk assessment methodology
+- Risk register with risk treatment plan
+- Statement of Applicability (SoA)
+- Asset inventory
+- Competence and awareness records
+- Internal audit reports
+- Management review minutes
+- Nonconformity and corrective action records
+
+---
+
+## 3. HIPAA for Health Tech Startups
+
+### When HIPAA Applies
+HIPAA applies if you are a **Covered Entity** (healthcare provider, health plan, clearinghouse) or a **Business Associate** (you process, store, or transmit Protected Health Information on behalf of a Covered Entity).
+
+**Key trigger:** If your product touches patient data in any way and a US healthcare provider uses your product, you are likely a Business Associate. You must sign a **BAA (Business Associate Agreement)** with each Covered Entity customer.
+
+### HIPAA Rule Structure
+| Rule | Focus | Key Requirements |
+|---|---|---|
+| Privacy Rule | How PHI can be used and disclosed | Minimum necessary, patient rights, notice of privacy practices |
+| Security Rule | Technical and physical safeguards for ePHI | Required and addressable safeguards |
+| Breach Notification Rule | What to do if PHI is breached | Timing and content of breach notifications |
+
+### Security Rule: Required vs. Addressable
+**Required safeguards** must be implemented exactly as specified. **Addressable safeguards** must be implemented or documented why an equivalent measure was used.
+
+**Key Required Safeguards:**
+- Unique user IDs (no shared logins)
+- Emergency access procedure
+- Audit controls (logging access to ePHI)
+- Transmission security (encryption in transit)
+- Person or entity authentication
+
+**Key Addressable Safeguards (implement or document why not):**
+- Automatic logoff
+- Encryption and decryption (encryption at rest — despite being "addressable," regulators expect it)
+- Audit review procedures
+- Security reminders and training
+
+### HIPAA Compliance Timeline
+
+| Phase | Duration | Activities |
+|---|---|---|
+| Risk analysis | 4–6 weeks | Document all PHI flows, assess risks to PHI — **required by law** |
+| Policy development | 4–8 weeks | Privacy policies, breach notification, workforce training |
+| Technical safeguard implementation | 4–12 weeks | Encryption, audit logging, access controls, BAA templates |
+| Workforce training | 2–4 weeks | Annual HIPAA training for all staff with PHI access |
+| BAA execution | Ongoing | Execute with all vendors who process PHI |
+| **Total** | **4–8 months** | — |
+
+### Cost Estimates
+| Item | Cost |
+|---|---|
+| Initial risk analysis (consultant) | $15,000–$40,000 |
+| Policy development | $8,000–$20,000 |
+| Technical implementation | $20,000–$60,000 |
+| Annual training and maintenance | $5,000–$15,000/yr |
+| HIPAA compliance platform | $10,000–$20,000/yr |
+| **Total first year** | **$45,000–$130,000** |
+
+### HIPAA Penalties (Why This Matters)
+| Violation Category | Penalty per Violation | Annual Cap |
+|---|---|---|
+| Unaware | $100–$50,000 | $25,000 |
+| Reasonable cause | $1,000–$50,000 | $100,000 |
+| Willful neglect (corrected) | $10,000–$50,000 | $250,000 |
+| Willful neglect (not corrected) | $50,000 | $1,500,000 |
+
+---
+
+## 4. GDPR Compliance Program
+
+### When GDPR Applies
+GDPR applies if you:
+- Are established in the EU/EEA
+- Process personal data of EU/EEA residents (regardless of your location)
+- Offer goods or services to EU residents
+- Monitor the behavior of EU residents
+
+**Key point for US startups:** If you have EU users or EU employees, GDPR applies to you.
+
+### Core GDPR Principles (Build These In)
+1. **Lawfulness, fairness, transparency** — have a legal basis for every processing activity
+2. **Purpose limitation** — collect data for specified, explicit purposes only
+3. **Data minimization** — collect only what you need
+4. **Accuracy** — keep data accurate
+5. **Storage limitation** — delete data when no longer needed
+6. **Integrity and confidentiality** — appropriate security measures
+7. **Accountability** — demonstrate compliance
+
+### Legal Bases for Processing
+| Basis | When to use |
+|---|---|
+| Consent | Marketing, non-essential cookies, optional features |
+| Contract | Processing necessary to deliver your service |
+| Legitimate interests | Analytics, fraud prevention, security (requires LIA) |
+| Legal obligation | Compliance with legal requirements |
+| Vital interests | Emergency situations only |
+
+**Avoid over-relying on consent** — it must be freely given, specific, informed, and unambiguous. Contractual basis is more robust for core product data.
+
+### GDPR Compliance Checklist
+
+**Governance:**
+- [ ] Data Protection Officer (DPO) appointed (required for large-scale processing or sensitive data)
+- [ ] Record of Processing Activities (RoPA) maintained
+- [ ] Data Protection Impact Assessments (DPIA) for high-risk processing
+
+**Rights Management (respond within 1 month):**
+- [ ] Right of access (data subject access requests — DSARs)
+- [ ] Right to rectification
+- [ ] Right to erasure ("right to be forgotten")
+- [ ] Right to data portability
+- [ ] Right to object to processing
+
+**Technical Measures:**
+- [ ] Privacy by design in product development
+- [ ] Data minimization enforced
+- [ ] Encryption at rest and in transit
+- [ ] Pseudonymization where possible
+- [ ] Retention policies and automated deletion
+
+**Vendor Management:**
+- [ ] Data Processing Agreements (DPAs) with all processors
+- [ ] Standard Contractual Clauses (SCCs) for non-EU transfers
+
+**Breach Notification:**
+- [ ] Notify supervisory authority within 72 hours of awareness
+- [ ] Notify affected individuals if high risk to their rights and freedoms
+
+### GDPR Compliance Timeline
+
+| Phase | Duration | Activities |
+|---|---|---|
+| Data mapping | 3–6 weeks | Map all personal data flows: collect, store, process, share, delete |
+| Legal basis review | 2–4 weeks | Assign legal basis to each processing activity |
+| Policy updates | 4–6 weeks | Privacy policy, cookie policy, employee data notices |
+| DPA execution | 2–4 weeks | Execute DPAs with all processors (SaaS vendors, cloud providers) |
+| Technical controls | 4–12 weeks | Consent management, data subject rights automation, retention |
+| Staff training | 2–4 weeks | GDPR awareness for all staff |
+| **Total** | **3–6 months** | — |
+
+### GDPR Fines
+- **Standard violations:** Up to €10M or 2% of global annual revenue
+- **Major violations** (basic principles, consent, data subject rights): Up to €20M or 4% of global annual revenue
+- **Highest ever fine:** Meta, €1.2B (2023, data transfers to US)
+
+---
+
+## 5. Multi-Framework Efficiency
+
+### Control Overlap Analysis
+
+The same underlying controls satisfy multiple frameworks. Build once, certify multiple times.
+
+**Core Control Domain Overlap:**
+
+| Control Domain | SOC 2 | ISO 27001 | HIPAA | GDPR |
+|---|---|---|---|---|
+| Access control / IAM | CC6 | A.5.15–A.5.18 | §164.312(a) | Art. 32 |
+| Encryption at rest/transit | CC6.7 | A.8.24 | §164.312(a)(2)(iv) | Art. 32 |
+| Audit logging | CC7.2 | A.8.15, A.8.17 | §164.312(b) | Art. 32 |
+| Incident response | CC7.3–CC7.5 | A.5.24–A.5.28 | §164.308(a)(6) | Art. 33–34 |
+| Vendor/third-party mgmt | CC9 | A.5.19–A.5.22 | §164.308(b) | Art. 28 |
+| Risk assessment | CC3 | Clause 6.1 | §164.308(a)(1) | Art. 32 |
+| Security training | CC1.4 | A.6.3, A.6.8 | §164.308(a)(5) | Art. 39 |
+| Business continuity | A1 | A.5.29–A.5.30 | §164.308(a)(7) | Art. 32 |
+| Data classification | CC6.1 | A.5.9–A.5.13 | §164.514 | Art. 5(1)(c) |
+| Change management | CC8 | A.8.32 | §164.312(c) | Art. 25 |
+
+**Efficiency Rule:** If you build SOC 2 controls correctly, you're ~65–75% of the way to ISO 27001 and ~70% of the way to HIPAA. Don't rebuild — extend.
+
+### Recommended Sequencing by Company Profile
+
+**B2B SaaS (US-focused):**
+```
+Month 0–6:   SOC 2 Type I → unblocks early enterprise deals
+Month 6–18:  SOC 2 Type II → enterprise table stakes
+Month 18–30: ISO 27001 → EU market expansion
+             (GDPR should be woven in from month 0 if any EU data)
+```
+
+**HealthTech (US):**
+```
+Month 0–8:   HIPAA compliance + BAA readiness → enables healthcare customers
+Month 6–18:  SOC 2 Type II → enterprise IT requirements on top of HIPAA
+Month 18+:   ISO 27001 if entering European market
+```
+
+**EU-founded SaaS:**
+```
+Month 0–3:   GDPR compliance → legal requirement, not optional
+Month 3–12:  ISO 27001 → EU enterprise default expectation
+Month 12–24: SOC 2 → US market expansion
+```
+
+**HealthTech (EU):**
+```
+Concurrent:  GDPR + ISO 27001 (strong overlap with MDR/IVDR security requirements)
+Month 12+:   HIPAA if entering US market
+```
+
+### Shared Evidence Model
+Build your evidence library once. Tag each piece of evidence by framework:
+
+```
+evidence/
+├── access_control/
+│   ├── iam_policy.pdf          [SOC2:CC6, ISO:A5.15, HIPAA:164.312a]
+│   ├── mfa_screenshot_Q1.png   [SOC2:CC6, ISO:A8.5, HIPAA:164.312d]
+│   └── access_review_log.xlsx  [SOC2:CC6, ISO:A5.18, HIPAA:164.308a]
+├── encryption/
+│   ├── kms_config.png          [SOC2:CC6.7, ISO:A8.24, HIPAA:164.312e]
+│   └── tls_policy.md           [SOC2:CC6.7, ISO:A8.24, HIPAA:164.312e]
+└── incident_response/
+    ├── ir_plan.pdf             [SOC2:CC7, ISO:A5.24, HIPAA:164.308a6]
+    └── tabletop_log.pdf        [SOC2:CC7, ISO:A5.26, HIPAA:164.308a6]
+```
+
+### GRC Platform Comparison
+
+| Platform | Best For | Price/yr | SOC 2 | ISO 27001 | HIPAA | GDPR |
+|---|---|---|---|---|---|---|
+| Vanta | Fast SOC 2, US startups | $15–30K | ✅ | ✅ | ✅ | ✅ |
+| Drata | Automation depth | $18–35K | ✅ | ✅ | ✅ | ✅ |
+| Secureframe | Cost-effective | $10–20K | ✅ | ✅ | ✅ | ✅ |
+| Sprinto | SMB, global | $12–25K | ✅ | ✅ | ✅ | ✅ |
+| Tugboat Logic | Mid-market | $20–40K | ✅ | ✅ | ✅ | ✅ |
+| Manual | Budget-constrained | $0 + time | ✅ | ✅ | ✅ | ✅ |
+
+**Recommendation:** For Series A startups, Vanta or Drata pays for itself in reduced auditor fees and internal time savings. Budget $15–25K/year.
+
+### Compliance Maintenance Annual Budget
+
+| Item | SOC 2 | ISO 27001 | HIPAA | GDPR |
+|---|---|---|---|---|
+| Annual audit / surveillance | $25–60K | $8–20K | n/a (self-assessed) | n/a (self-assessed) |
+| GRC platform | $15–30K | Shared | Shared | Shared |
+| Annual training | $3–8K | Shared | Shared | Shared |
+| Policy review | $2–5K | $2–5K | $2–5K | $2–5K |
+| **Total ongoing** | **$45–103K/yr** | **+$10–25K/yr** | **+$5–15K/yr** | **+$5–15K/yr** |