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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

Best for

    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

    PlatformStatusEvidenceWhat to check
    CodexNot declaredNo explicit evidencePortability before use
    Claude CodeNot declaredNo explicit evidencePortability before use
    CursorNot declaredNo explicit evidencePortability before use
    Gemini CLINot declaredNo explicit evidencePortability before use
    Open the compatibility checker

    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.

    Source-detected install commandSource
    npx skills add https://github.com/vibeeval/vibecosystem --skill "skills/cto-advisor"
    Safe inspection promptEditorial

    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

    1. 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)
    2. 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.
    3. 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)
    4. 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.
    5. 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

    EvidenceSourceComputedTestedEditorial
    SignalValueEvidence typeMeaning
    Quality score92/100ComputedDocumentation, specificity, maintenance, and trust rules
    Repository stars528SourceRepository attention, not individual Skill quality
    Compatibility0 platformsSourceDeclared in the catalog source record
    Usage guideautomated source guideEditorialGenerated 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

    ConditionRecommendation
    Core differentiatorBUILD (competitive advantage)
    Commodity capabilityBUY (focus on core)
    Strict compliance / data sovereigntyBUILD (control)
    Team has no domain expertiseBUY (faster, less risk)
    Vendor lock-in risk > 7/10BUILD or multi-vendor
    Time to market < 3 monthsBUY (speed)
    Budget constrained, long-termBUILD (lower TCO)

    Build vs Buy Anti-Patterns

    Anti-PatternNeden YanlisDogru Yol
    "Not invented here"Wasted engineering timeEvaluate vendors objectively
    "We'll build it in 2 weeks"Always takes 5x longerRealistic estimation with buffer
    Buying everythingNo differentiationBuild core, buy commodity
    Ignoring maintenance costBuild looks cheaper initiallyInclude 3-5 year maintenance TCO
    No exit strategy from vendorLock-in trapEvaluate migration cost upfront

    Tech Debt Quantification & Prioritization

    Tech Debt Classification

    TypeDescriptionImpactExample
    Code debtPoor code qualityDeveloper velocityNo types, huge functions, no tests
    Architecture debtWrong architectural decisionsScalabilityMonolith that should be microservice
    Test debtInsufficient test coverageReliabilityNo integration tests, flaky tests
    Dependency debtOutdated dependenciesSecurity3 major versions behind, CVEs
    Documentation debtMissing/outdated docsOnboardingNo API docs, stale README
    Infrastructure debtManual processes, legacy infraReliabilityNo CI/CD, manual deployments
    Design debtUX inconsistenciesUser experience5 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

    PatternWhen to UseSize
    Stream-alignedProduct features5-8 people
    PlatformInternal tooling, infrastructure3-5 people
    EnablingCoach other teams, remove blockers2-3 people
    Complicated subsystemDeep 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-PatternRiskDogru Yol
    Resume-driven developmentWrong tool for the jobEvaluate against actual needs
    Hype-driven adoptionImmature ecosystemWait for version 2.0+
    Single vendor evaluationNo comparison baselineAlways evaluate 3+ options
    Ignoring exit costFuture lock-inCalculate migration cost
    No POC/prototypeUnknown unknownsBuild 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

    RiskLikelihoodImpactMitigation
    Vendor acquired/shutdownLowCriticalData export procedure, backup vendor
    Price increase > 30%MediumHighMulti-year contract, alternative evaluation
    SLA breachMediumHighCredits, contractual remedies
    Data breach at vendorLowCriticalEncryption, contractual liability
    Feature deprecationMediumMediumAPI abstraction layer

    Engineering Metrics

    DORA Metrics

    MetricEliteHighMediumLow
    Deployment FrequencyOn-demand (multiple/day)Daily-weeklyWeekly-monthlyMonthly-6monthly
    Lead Time for Changes< 1 hour1 day - 1 week1 week - 1 month1 - 6 months
    Change Failure Rate0-15%16-30%16-30%16-30%
    Mean Time to Recovery< 1 hour< 1 day1 day - 1 week> 1 week

    SPACE Framework

    DimensionMetricsHow to Measure
    SatisfactionDeveloper satisfaction surveyQuarterly survey (1-5 scale)
    PerformanceCode review turnaround, incident resolutionTooling metrics
    ActivityPRs merged, deploys, commitsGit/CI data (NOT for evaluation)
    CommunicationKnowledge sharing, documentationSurvey + doc metrics
    EfficiencyDev environment setup time, build timeMeasure 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-PatternNeden YanlisDogru Yol
    Too much jargonBoard members aren't engineersTranslate to business impact
    Only good newsErodes trustHonest + solution-oriented
    No metricsUnverifiableData-driven with trends
    Feature list onlyNo business contextConnect features to revenue/growth
    Asking for budget without ROIUnlikely approvalShow 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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