Skill: ivangdavila/cio (version 1.0.0)

--- name: Chief Information Officer slug: cio description: Drive IT strategy, digital transformation, vendor management, architecture decisions, and technology governance. --- ## When to Use User wants technology leadership for their company, startup, or project. Agent acts as virtual CIO handling IT strategy, infrastructure, and digital initiatives. ## Quick Reference | Topic | File | |-------|------| | IT strategy frameworks | `strategy.md` | | Vendor evaluation and management | `vendors.md` | | Architecture decision records | `architecture.md` | | Digital transformation playbooks | `transformation.md` | ## Core Capabilities 1. **Set IT strategy** — Technology vision, multi-year roadmap, build vs buy decisions 2. **Drive digital transformation** — Process automation, cloud migration, legacy modernization 3. **Manage vendors** — RFP creation, contract negotiation, SLA monitoring, vendor consolidation 4. **Govern architecture** — Tech standards, ADRs, integration patterns, technical debt tracking 5. **Control IT budget** — Cost allocation, ROI analysis, license optimization, cloud spend 6. **Run IT operations** — Uptime targets, disaster recovery, change management, ITSM 7. **Enable data strategy** — Data governance, analytics platforms, data quality, privacy compliance ## Decision Checklist Before recommending IT direction, ask: - [ ] Company stage? (startup, growth, enterprise) - [ ] Team size? (no IT, small team, IT department) - [ ] Current stack? (cloud-native, hybrid, legacy on-prem) - [ ] Industry constraints? (regulated, compliance requirements) - [ ] Budget posture? (constrained, growth mode, optimization) ## Critical Rules - **Business outcomes first** — Technology serves business goals, not the reverse - **Total cost of ownership** — Include migration, training, maintenance in all decisions - **Reduce complexity** — Every new system adds operational burden - **Vendor leverage** — Multi-year deals need exit clauses; avoid lock-in - **Technical debt interest** — Track and pay down; ignoring it compounds - **Shadow IT signals needs** — When teams go rogue, IT isn't serving them ## By Company Stage | Stage | Focus | |-------|-------| | **Seed/Series A** | Cloud-first stack, minimal vendors, scalable foundations, developer productivity | | **Series B** | IT policies, vendor consolidation, security baseline, data infrastructure | | **Series C+** | Enterprise architecture, IT governance board, M&A tech diligence, regional expansion |

path: architecture.md
content: # Architecture Decisions

## ADR Template (Architecture Decision Record)

```markdown
# ADR-XXX: [Title]

## Status
[Proposed | Accepted | Deprecated | Superseded by ADR-YYY]

## Context
What is the issue that we're seeing that is motivating this decision?

## Decision
What is the change that we're proposing and/or doing?

## Consequences
What becomes easier or more difficult to do because of this change?

## Alternatives Considered
What other options were evaluated?
```

## Integration Patterns

| Pattern | When to Use |
|---------|-------------|
| **API-first** | Real-time needs, tight coupling acceptable |
| **Event-driven** | Loose coupling, eventual consistency OK |
| **Batch/ETL** | Large volumes, latency tolerant |
| **File transfer** | Legacy systems, simple needs |

## Technical Debt Categories

| Type | Example | Impact |
|------|---------|--------|
| **Code** | No tests, copy-paste | Slow feature delivery |
| **Architecture** | Monolith needing split | Scale ceiling |
| **Infrastructure** | Manual deployments | Reliability risk |
| **Documentation** | Tribal knowledge | Bus factor |
| **Dependency** | Outdated libraries | Security risk |

## Debt Tracking Template

| ID | Description | Type | Impact | Effort | Priority |
|----|-------------|------|--------|--------|----------|
| | | | H/M/L | S/M/L/XL | |

## Technology Standards

### Approved Stack
- **Languages:** [List approved languages]
- **Frameworks:** [List approved frameworks]
- **Databases:** [List approved databases]
- **Cloud:** [Approved providers]
- **Monitoring:** [Approved tools]

### Exception Process
1. Submit exception request with justification
2. Architecture review (impact, support, exit plan)
3. CIO/CTO approval for production use
4. Document in tech radar as Trial/Assess

## System Criticality Tiers

| Tier | Definition | RTO | RPO |
|------|------------|-----|-----|
| **Tier 1** | Business stops | <1hr | <15min |
| **Tier 2** | Major impact | <4hr | <1hr |
| **Tier 3** | Workarounds exist | <24hr | <4hr |
| **Tier 4** | Minor inconvenience | <72hr | <24hr |


path: strategy.md
content: # IT Strategy Frameworks

## Strategy Document Template

```markdown
# IT Strategy 20XX-20XX

## Vision
Where technology takes the business in 3-5 years.

## Current State Assessment
- Infrastructure: [cloud/hybrid/on-prem]
- Technical debt: [low/medium/high]
- Team capability: [gaps identified]
- Vendor landscape: [key dependencies]

## Strategic Pillars
1. [Pillar 1] — e.g., Cloud-first migration
2. [Pillar 2] — e.g., Data platform modernization
3. [Pillar 3] — e.g., Developer experience

## Initiatives by Pillar
| Pillar | Initiative | Timeline | Investment |
|--------|-----------|----------|------------|
| | | | |

## Success Metrics
- [Metric 1]: Current → Target
- [Metric 2]: Current → Target

## Risks and Mitigations
| Risk | Impact | Mitigation |
|------|--------|------------|
| | | |

## Governance
- Review cadence: [quarterly]
- Decision forum: [IT steering committee]
```

## Build vs Buy Framework

### Default to Buy When:
- Commodity capability (email, HR systems, CRM)
- Time-to-market is critical
- Maintenance burden is high
- Vendor ecosystem is mature

### Default to Build When:
- Core competitive advantage
- Unique business logic
- Integration requirements are extreme
- Vendor options don't fit

### Evaluation Criteria
| Factor | Weight | Build Score | Buy Score |
|--------|--------|-------------|-----------|
| Time to value | | | |
| Total cost (5yr) | | | |
| Customization need | | | |
| Maintenance burden | | | |
| Strategic fit | | | |

## Technology Radar

Track technology adoption status:

| Ring | Meaning |
|------|---------|
| **Adopt** | Ready for production, recommended |
| **Trial** | Worth pursuing, proof of concept stage |
| **Assess** | Exploring, not yet committed |
| **Hold** | Do not start new projects with this |

Categories:
- Languages & Frameworks
- Infrastructure & Platforms
- Tools
- Techniques

## Annual Planning Cycle

| Month | Activity |
|-------|----------|
| Q4 | Strategy review, next year planning |
| Q1 | Budget finalization, initiative kickoff |
| Q2 | Mid-year progress review |
| Q3 | Strategic adjustments, pre-planning |


path: transformation.md
content: # Digital Transformation Playbooks

## Cloud Migration

### Migration Strategies (6 Rs)

| Strategy | Description | When to Use |
|----------|-------------|-------------|
| **Rehost** | Lift and shift | Quick wins, minimal change |
| **Replatform** | Lift and optimize | Minor cloud benefits |
| **Repurchase** | Move to SaaS | Commodity workloads |
| **Refactor** | Re-architect | Cloud-native benefits needed |
| **Retire** | Decommission | No longer needed |
| **Retain** | Keep on-prem | Compliance, latency, cost |

### Migration Checklist
- [ ] Application inventory complete
- [ ] Dependencies mapped
- [ ] Data classification done
- [ ] Landing zone ready
- [ ] Network connectivity tested
- [ ] Security controls configured
- [ ] Runbooks updated
- [ ] Rollback plan documented

## Legacy Modernization

### Assessment Framework

| Factor | Current | Target | Gap |
|--------|---------|--------|-----|
| Maintainability | | | |
| Scalability | | | |
| Security posture | | | |
| Operational cost | | | |
| Developer productivity | | | |

### Modernization Patterns

| Pattern | Approach |
|---------|----------|
| **Strangler fig** | Gradually replace pieces |
| **Branch by abstraction** | Abstract, switch, remove |
| **Parallel run** | Run both, compare results |
| **Big bang** | Full replacement (risky) |

## Process Automation

### Automation Candidates

Score each process:
| Criteria | Weight |
|----------|--------|
| Volume (transactions/month) | 25% |
| Repetitiveness | 20% |
| Rule-based (vs judgment) | 20% |
| Error rate | 15% |
| Time per transaction | 10% |
| Strategic value | 10% |

### Automation Stack Options

| Type | Tools | Best For |
|------|-------|----------|
| **RPA** | UiPath, Automation Anywhere | Legacy UI automation |
| **iPaaS** | Zapier, Workato, Tray | API integrations |
| **Low-code** | Retool, Appsmith | Internal tools |
| **Custom** | Python, Node.js | Complex logic |

## Change Management

### Stakeholder Matrix

| Stakeholder | Impact | Influence | Strategy |
|-------------|--------|-----------|----------|
| | H/M/L | H/M/L | Inform/Consult/Involve |

### Adoption Metrics

- Awareness: % who know about change
- Understanding: % who understand why
- Adoption: % actively using
- Proficiency: % using effectively


path: vendors.md
content: # Vendor Management

## Vendor Evaluation Scorecard

| Criteria | Weight | Score (1-5) | Notes |
|----------|--------|-------------|-------|
| **Fit** | | | |
| Feature coverage | 20% | | |
| Integration capability | 15% | | |
| Scalability | 10% | | |
| **Risk** | | | |
| Financial stability | 10% | | |
| Security posture | 15% | | |
| Vendor lock-in | 10% | | |
| **Economics** | | | |
| Total cost (3yr) | 15% | | |
| Implementation cost | 5% | | |

## RFP Template Structure

1. **Company Overview** — Who you are, what you need
2. **Requirements** — Functional, technical, integration
3. **Evaluation Criteria** — How you'll score
4. **Timeline** — Key dates, decision process
5. **Pricing Request** — Format you need
6. **Security Questionnaire** — Your standard questions
7. **References** — Similar customers to contact

## Contract Negotiation Checklist

- [ ] Multi-year discount secured (15-30% typical)
- [ ] Exit clause defined (data export, transition period)
- [ ] SLA with financial penalties
- [ ] Price cap on renewals (3-5% max increase)
- [ ] Audit rights for compliance
- [ ] Data ownership explicitly stated
- [ ] Sub-processor notification requirements
- [ ] Termination for convenience clause

## Vendor Consolidation

### Signs You Need Consolidation:
- Multiple tools doing same job
- Integration overhead is high
- License spend is fragmented
- Support relationships too many

### Consolidation Process:
1. Inventory all vendors (spend, users, contracts)
2. Map to capability categories
3. Identify overlap and gaps
4. Score vendors in each category
5. Build migration plan with timeline
6. Execute with change management

## SLA Monitoring

| Metric | Target | Current | Trend |
|--------|--------|---------|-------|
| Uptime | 99.9% | | |
| Response time | <200ms | | |
| Support response | <4hrs | | |
| Incident resolution | <24hrs | | |

## Vendor Risk Tiers

| Tier | Criteria | Review Cadence |
|------|----------|----------------|
| **Critical** | Business stops without them | Quarterly |
| **Important** | Significant impact | Semi-annual |
| **Standard** | Limited blast radius | Annual |


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