vibeeval/vibecosystem/skills/cto-advisor/SKILL.md
cto-advisor
CTO-level advisory - build vs buy decisions, tech debt quantification, team scaling, ADRs, technology evaluation (RICE), budget planning, TCO, vendor management, DORA/SPACE metrics
- Source repository stars
- 528
- Declared platforms
- 0
- Static risk flags
- 0
- Last source update
- 2026-08-08
- Source checked
- 2026-08-25
Decision brief
What it does: where it fits
CTO-level advisory - build vs buy decisions, tech debt quantification, team scaling, ADRs, technology evaluation (RICE), budget planning, TCO, vendor management, DORA/SPACE metrics
Not for
- Tasks that require unconfirmed production actions or broad system permissions.
- Environments where the pinned source and install steps cannot be inspected.
Compatibility matrix
Platform support, with evidence labels
| Platform | Status | Evidence | What to check |
|---|---|---|---|
| Codex | Not declared | No explicit evidence | Portability before use |
| Claude Code | Not declared | No explicit evidence | Portability before use |
| Cursor | Not declared | No explicit evidence | Portability before use |
| Gemini CLI | Not declared | No explicit evidence | Portability before use |
Installation
Inspect first. Install second.
The source command is displayed only when detected. A safe inspection prompt is always available so your agent can explain every action before execution.
npx skills add https://github.com/vibeeval/vibecosystem --skill "skills/cto-advisor"Inspect the Agent Skill "cto-advisor" from https://github.com/vibeeval/vibecosystem/blob/3b763b1fb288f57bfa3cce76ef18184b96461a78/skills/cto-advisor/SKILL.md at commit 3b763b1fb288f57bfa3cce76ef18184b96461a78. List every install step, command, network request, credential, file read/write, external action, and rollback step. Explain whether it fits my task. Do not install or execute anything until I approve.
Workflow
What the source asks the agent to do
- 01
Tech Debt Assessment: [Project Name]
[If we don't address debt area X, what happens in 6 months?]
[If we don't address debt area X, what happens in 6 months?]Priority Score = (Impact Urgency Spread) / EffortImpact (1-5): How much does it slow the team? Urgency (1-5): How quickly will it get worse? Spread (1-5): How many areas does it affect? Effort (1-5): How hard is it to fix? (inverse: 1=hard, 5=easy) - 02
Year 1 (Setup + Operations)
Review the “Year 1 (Setup + Operations)” section in the pinned source before continuing.
Review and apply the “Year 1 (Setup + Operations)” source section. - 03
Vendor Assessment Checklist
[ ] Financial stability (will they exist in 3 years?)
[ ] Financial stability (will they exist in 3 years?)[ ] Security certifications (SOC2, ISO 27001)[ ] SLA guarantees (uptime, response time) - 04
Build vs Buy Decision Framework
Review the “Build vs Buy Decision Framework” section in the pinned source before continuing.
Review and apply the “Build vs Buy Decision Framework” source section. - 05
Decision Matrix
Review the “Decision Matrix” section in the pinned source before continuing.
Review and apply the “Decision Matrix” source section.
Permission review
Static risk signals and limitations
No configured static risk pattern was detected
This is not proof of safety. Runtime behavior, indirect dependencies, and hidden external systems are outside the static scan.
Evidence record
Why each signal appears
| Signal | Value | Evidence type | Meaning |
|---|---|---|---|
| Quality score | 92/100 | Computed | Documentation, specificity, maintenance, and trust rules |
| Repository stars | 528 | Source | Repository attention, not individual Skill quality |
| Compatibility | 0 platforms | Source | Declared in the catalog source record |
| Usage guide | automated source guide | Editorial | Generated or reviewed according to the visible evidence level |
Pinned source
Provenance and original SKILL.md
- Repository
- vibeeval/vibecosystem
- Skill path
- skills/cto-advisor/SKILL.md
- Commit
- 3b763b1fb288f57bfa3cce76ef18184b96461a78
- License
- MIT
- Collected
- 2026-08-25
- Default branch
- main
View the original SKILL.md
CTO Advisor
Build vs Buy Decision Framework
Decision Matrix
## Build vs Buy Analysis: [Feature/System Name]
### Scoring (1-5 each)
| Factor | Build | Buy | Weight |
|--------|-------|-----|--------|
| Core competency alignment | [1-5] | [1-5] | 3x |
| Time to market | [1-5] | [1-5] | 2x |
| Total cost (3 year) | [1-5] | [1-5] | 2x |
| Customization needs | [1-5] | [1-5] | 2x |
| Maintenance burden | [1-5] | [1-5] | 1x |
| Data control | [1-5] | [1-5] | 1x |
| Integration complexity | [1-5] | [1-5] | 1x |
| Vendor risk | [1-5] | [1-5] | 1x |
| **Weighted Total** | [sum] | [sum] | |
### Decision: BUILD / BUY / HYBRID
Decision Rules
| Condition | Recommendation |
|---|---|
| Core differentiator | BUILD (competitive advantage) |
| Commodity capability | BUY (focus on core) |
| Strict compliance / data sovereignty | BUILD (control) |
| Team has no domain expertise | BUY (faster, less risk) |
| Vendor lock-in risk > 7/10 | BUILD or multi-vendor |
| Time to market < 3 months | BUY (speed) |
| Budget constrained, long-term | BUILD (lower TCO) |
Build vs Buy Anti-Patterns
| Anti-Pattern | Neden Yanlis | Dogru Yol |
|---|---|---|
| "Not invented here" | Wasted engineering time | Evaluate vendors objectively |
| "We'll build it in 2 weeks" | Always takes 5x longer | Realistic estimation with buffer |
| Buying everything | No differentiation | Build core, buy commodity |
| Ignoring maintenance cost | Build looks cheaper initially | Include 3-5 year maintenance TCO |
| No exit strategy from vendor | Lock-in trap | Evaluate migration cost upfront |
Tech Debt Quantification & Prioritization
Tech Debt Classification
| Type | Description | Impact | Example |
|---|---|---|---|
| Code debt | Poor code quality | Developer velocity | No types, huge functions, no tests |
| Architecture debt | Wrong architectural decisions | Scalability | Monolith that should be microservice |
| Test debt | Insufficient test coverage | Reliability | No integration tests, flaky tests |
| Dependency debt | Outdated dependencies | Security | 3 major versions behind, CVEs |
| Documentation debt | Missing/outdated docs | Onboarding | No API docs, stale README |
| Infrastructure debt | Manual processes, legacy infra | Reliability | No CI/CD, manual deployments |
| Design debt | UX inconsistencies | User experience | 5 different button styles |
Tech Debt Scorecard
## Tech Debt Assessment: [Project Name]
| Area | Score (1-10) | Trend | Priority |
|------|-------------|-------|----------|
| Code quality | [X] | [up/down/flat] | [H/M/L] |
| Test coverage | [X%] | [up/down/flat] | [H/M/L] |
| Dependency freshness | [X] | [up/down/flat] | [H/M/L] |
| Build/deploy time | [X min] | [up/down/flat] | [H/M/L] |
| Documentation | [X] | [up/down/flat] | [H/M/L] |
| Security posture | [X] | [up/down/flat] | [H/M/L] |
### Cost of Delay
[If we don't address debt area X, what happens in 6 months?]
### Investment Request
| Initiative | Effort | Impact | ROI Period |
|-----------|--------|--------|------------|
| [debt 1] | [weeks] | [description] | [months] |
| [debt 2] | [weeks] | [description] | [months] |
Prioritization Formula
Priority Score = (Impact * Urgency * Spread) / Effort
Impact (1-5): How much does it slow the team?
Urgency (1-5): How quickly will it get worse?
Spread (1-5): How many areas does it affect?
Effort (1-5): How hard is it to fix? (inverse: 1=hard, 5=easy)
Tech Debt Budget Rule
RULE: 20% of sprint capacity reserved for tech debt reduction
Sprint capacity: 10 story points
├── 8 points: Feature work
└── 2 points: Tech debt reduction (ZORUNLU, negotiable degil)
Team Scaling Strategies
Hiring Framework
## Hiring Plan: [Quarter/Year]
### Current State
| Role | Headcount | Capacity | Gap |
|------|-----------|----------|-----|
| Backend | [X] | [Y features/quarter] | [shortfall] |
| Frontend | [X] | [Y features/quarter] | [shortfall] |
| DevOps | [X] | [Y deploys/week] | [shortfall] |
| QA | [X] | [Y tests/sprint] | [shortfall] |
### Ratios
- Engineer : Manager = 6-8 : 1
- Senior : Mid : Junior = 2 : 3 : 1
- Backend : Frontend = project-dependent
- Engineer : QA = 4-6 : 1
### Onboarding Milestones
| Day | Milestone |
|-----|-----------|
| 1 | Dev environment running, first commit |
| 7 | First PR merged |
| 14 | First feature shipped to staging |
| 30 | Independent task completion |
| 60 | Contributing to architecture discussions |
| 90 | Fully productive, mentoring others |
Team Topology Patterns
| Pattern | When to Use | Size |
|---|---|---|
| Stream-aligned | Product features | 5-8 people |
| Platform | Internal tooling, infrastructure | 3-5 people |
| Enabling | Coach other teams, remove blockers | 2-3 people |
| Complicated subsystem | Deep expertise (ML, security) | 2-4 people |
Architecture Decision Records (ADR)
ADR Template
# ADR-[number]: [decision title]
## Status
[Proposed | Accepted | Deprecated | Superseded by ADR-XXX]
## Context
[What is the issue? What forces are at play?]
[Include constraints, requirements, team capabilities]
## Decision
[What is the change that we're proposing and/or doing?]
## Alternatives Considered
### Option A: [name]
- Pros: [list]
- Cons: [list]
### Option B: [name]
- Pros: [list]
- Cons: [list]
## Consequences
### Positive
- [benefit 1]
- [benefit 2]
### Negative
- [tradeoff 1]
- [tradeoff 2]
### Risks
- [risk 1]: [mitigation]
- [risk 2]: [mitigation]
## Decision Date
[YYYY-MM-DD]
## Decision Makers
[names/roles]
ADR Index
## Architecture Decision Log
| # | Decision | Status | Date | Impact |
|---|---------|--------|------|--------|
| 001 | Use PostgreSQL over MongoDB | Accepted | 2025-01-15 | High |
| 002 | Adopt microservices for billing | Accepted | 2025-02-01 | High |
| 003 | Use React over Vue | Accepted | 2025-02-15 | Medium |
| 004 | Monolith-first for MVP | Deprecated | 2025-03-01 | High |
Technology Evaluation Framework
RICE Scoring
## Technology Evaluation: [Technology Name]
### RICE Score
| Factor | Score | Weight | Weighted |
|--------|-------|--------|----------|
| **Reach** (how many people/teams affected) | [1-10] | 1x | [X] |
| **Impact** (how much improvement per person) | [1-3: minimal/medium/massive] | 2x | [X] |
| **Confidence** (how sure are we) | [50-100%] | 1x | [X] |
| **Effort** (person-months) | [X] | divisor | [X] |
**RICE Score = (Reach * Impact * Confidence) / Effort = [score]**
Weighted Scoring Matrix
## Vendor/Technology Comparison
| Criteria | Weight | Option A | Option B | Option C |
|----------|--------|----------|----------|----------|
| Performance | 20% | [1-5] | [1-5] | [1-5] |
| Community/support | 15% | [1-5] | [1-5] | [1-5] |
| Learning curve | 15% | [1-5] | [1-5] | [1-5] |
| Cost | 15% | [1-5] | [1-5] | [1-5] |
| Scalability | 10% | [1-5] | [1-5] | [1-5] |
| Security | 10% | [1-5] | [1-5] | [1-5] |
| Integration | 10% | [1-5] | [1-5] | [1-5] |
| Maturity | 5% | [1-5] | [1-5] | [1-5] |
| **Weighted Total** | | [sum] | [sum] | [sum] |
### Recommendation: [Option X]
### Reasoning: [1-2 sentences]
Technology Evaluation Anti-Patterns
| Anti-Pattern | Risk | Dogru Yol |
|---|---|---|
| Resume-driven development | Wrong tool for the job | Evaluate against actual needs |
| Hype-driven adoption | Immature ecosystem | Wait for version 2.0+ |
| Single vendor evaluation | No comparison baseline | Always evaluate 3+ options |
| Ignoring exit cost | Future lock-in | Calculate migration cost |
| No POC/prototype | Unknown unknowns | Build spike before committing |
Budget Planning & TCO Analysis
TCO Template (3-Year)
## Total Cost of Ownership: [System/Technology]
### Year 1 (Setup + Operations)
| Category | Cost |
|----------|------|
| Licenses/subscriptions | $[X] |
| Infrastructure (cloud/hardware) | $[X] |
| Implementation/migration | $[X] |
| Training | $[X] |
| Integration development | $[X] |
| **Year 1 Total** | **$[X]** |
### Year 2-3 (Ongoing)
| Category | Annual Cost |
|----------|------------|
| Licenses/subscriptions (+ annual increase) | $[X] |
| Infrastructure | $[X] |
| Maintenance engineering (FTE fraction) | $[X] |
| Support contracts | $[X] |
| Upgrades/patches | $[X] |
| **Annual Ongoing** | **$[X]** |
### 3-Year TCO: $[Year 1 + Year 2 + Year 3]
### Hidden Costs (often missed)
- Context switching overhead
- On-call/incident response time
- Documentation maintenance
- Vendor management overhead
- Compliance/audit costs
Vendor Management
Vendor Assessment Checklist
- Financial stability (will they exist in 3 years?)
- Security certifications (SOC2, ISO 27001)
- SLA guarantees (uptime, response time)
- Data portability (can you export everything?)
- API quality (documentation, versioning, reliability)
- Support quality (response time, escalation path)
- Pricing transparency (no surprise costs)
- Contract flexibility (monthly vs annual, exit clause)
- Reference customers (talk to existing users)
- Roadmap alignment (are they building what you need?)
Vendor Risk Matrix
| Risk | Likelihood | Impact | Mitigation |
|---|---|---|---|
| Vendor acquired/shutdown | Low | Critical | Data export procedure, backup vendor |
| Price increase > 30% | Medium | High | Multi-year contract, alternative evaluation |
| SLA breach | Medium | High | Credits, contractual remedies |
| Data breach at vendor | Low | Critical | Encryption, contractual liability |
| Feature deprecation | Medium | Medium | API abstraction layer |
Engineering Metrics
DORA Metrics
| Metric | Elite | High | Medium | Low |
|---|---|---|---|---|
| Deployment Frequency | On-demand (multiple/day) | Daily-weekly | Weekly-monthly | Monthly-6monthly |
| Lead Time for Changes | < 1 hour | 1 day - 1 week | 1 week - 1 month | 1 - 6 months |
| Change Failure Rate | 0-15% | 16-30% | 16-30% | 16-30% |
| Mean Time to Recovery | < 1 hour | < 1 day | 1 day - 1 week | > 1 week |
SPACE Framework
| Dimension | Metrics | How to Measure |
|---|---|---|
| Satisfaction | Developer satisfaction survey | Quarterly survey (1-5 scale) |
| Performance | Code review turnaround, incident resolution | Tooling metrics |
| Activity | PRs merged, deploys, commits | Git/CI data (NOT for evaluation) |
| Communication | Knowledge sharing, documentation | Survey + doc metrics |
| Efficiency | Dev environment setup time, build time | Measure and track |
Engineering Health Dashboard
## Engineering Health: [Quarter]
### DORA Metrics
| Metric | Target | Actual | Status |
|--------|--------|--------|--------|
| Deploy frequency | Daily | [X/week] | [on/off track] |
| Lead time | < 1 day | [X hours] | [on/off track] |
| Change failure rate | < 15% | [X%] | [on/off track] |
| MTTR | < 1 hour | [X min] | [on/off track] |
### Team Health
| Area | Score (1-10) | Trend |
|------|-------------|-------|
| Developer satisfaction | [X] | [up/down/flat] |
| On-call burden | [X] | [up/down/flat] |
| Tech debt sentiment | [X] | [up/down/flat] |
| Tooling satisfaction | [X] | [up/down/flat] |
### Actionable Insights
1. [Insight + recommended action]
2. [Insight + recommended action]
Board/Investor Technical Reporting
Quarterly Tech Report Template
## Technology Report: Q[X] [Year]
### Executive Summary
[2-3 sentences: key wins, risks, requests]
### Key Metrics
| Metric | Q-1 | Q0 | Target | Trend |
|--------|-----|-----|--------|-------|
| Uptime | [X%] | [X%] | 99.9% | [arrow] |
| Page load time | [Xs] | [Xs] | < 2s | [arrow] |
| Active users | [X] | [X] | [target] | [arrow] |
| Deploy frequency | [X/mo] | [X/mo] | Daily | [arrow] |
### Achievements
1. [Milestone/launch/improvement]
2. [Milestone/launch/improvement]
### Risks & Challenges
| Risk | Severity | Mitigation | Status |
|------|----------|-----------|--------|
| [risk] | [H/M/L] | [plan] | [active/mitigated] |
### Budget
| Category | Budget | Actual | Variance |
|----------|--------|--------|----------|
| Infrastructure | $[X] | $[X] | [+/-X%] |
| Licenses | $[X] | $[X] | [+/-X%] |
| Headcount | $[X] | $[X] | [+/-X%] |
### Next Quarter Focus
1. [Priority 1]
2. [Priority 2]
3. [Priority 3]
### Resource Request
[If applicable: what do we need and why]
Board Communication Anti-Patterns
| Anti-Pattern | Neden Yanlis | Dogru Yol |
|---|---|---|
| Too much jargon | Board members aren't engineers | Translate to business impact |
| Only good news | Erodes trust | Honest + solution-oriented |
| No metrics | Unverifiable | Data-driven with trends |
| Feature list only | No business context | Connect features to revenue/growth |
| Asking for budget without ROI | Unlikely approval | Show expected return |
Frequently asked questions
What to verify before installation and use
What does the cto-advisor source document cover?
CTO-level advisory - build vs buy decisions, tech debt quantification, team scaling, ADRs, technology evaluation (RICE), budget planning, TCO, vendor management, DORA/SPACE metrics
How do I install cto-advisor?
The source record exposes this install command: npx skills add https://github.com/vibeeval/vibecosystem --skill "skills/cto-advisor". Inspect the command and pinned source before running it.
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