Case Study: Migrating a 50-Developer Team to SpecWeave

A practical walkthrough of adopting SpecWeave in an enterprise environment.

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Company Profile

Aspect	Details
Team size	50 developers, 8 teams
Tech stack	React, Node.js, PostgreSQL
Existing tools	JIRA, GitHub Enterprise
Pain points	Stale docs, unclear specs, slow onboarding
Timeline	8 weeks to production use

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The Problem

Before SpecWeave

Reality at AcmeCorp:
┌─────────────────────────────────────────────────┐
│ JIRA                                            │
│ - 2,000+ tickets (50% stale)                   │
│ - Descriptions out of sync with code           │
│ - No one trusts requirements                   │
└─────────────────────────────────────────────────┘
        │ Manual copy-paste (often forgotten)
        ↓
┌─────────────────────────────────────────────────┐
│ GitHub                                          │
│ - PRs have minimal context                     │
│ - READMEs outdated                             │
│ - Architecture decisions lost                  │
└─────────────────────────────────────────────────┘
        │ Tribal knowledge
        ↓
┌─────────────────────────────────────────────────┐
│ Developer Heads                                 │
│ - Onboarding takes 2-3 months                  │
│ - "Ask Sarah, she knows this"                  │
│ - Knowledge silos                              │
└─────────────────────────────────────────────────┘

Symptoms:

• New developers took 3 months to be productive
• 40% of bugs were due to unclear requirements
• Same questions asked repeatedly
• "I thought we already decided this"

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Week 1: Planning

Day 1-2: Assessment

## Migration Assessment

### Inventory
- 12 microservices
- 3 web applications
- 2 mobile apps
- 180,000 lines of code

### Priority Projects
1. payment-service (critical, active development)
2. user-service (high churn, many bugs)
3. web-app (largest team, most confusion)

### Stakeholders
- Engineering VP: Sponsor
- 3 Team Leads: Champions
- 50 Developers: Users
- 5 PMs: Beneficiaries

Day 3-5: Pilot Team Selection

Criteria for pilot team:

• ✅ Open to new tools
• ✅ Active development
• ✅ Clear pain points
• ✅ Strong tech lead

Selected: Payment team (8 developers)

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Week 2: Pilot Setup

Day 1: SpecWeave Installation

# In payment-service repo
specweave init

# During setup:
? External tool integration: JIRA Cloud
? JIRA project: PAYMENTS
? GitHub repo: acmecorp/payment-service
? Living docs strategy: Bidirectional sync

Day 2-3: Initial Documentation

Used brownfield quick-start approach:

# Import critical documentation only
/sw:import-docs --source=confluence --filter="payment*"

# Result: Created minimal living docs structure
.specweave/
├── docs/
│   ├── living/
│   │   ├── modules/
│   │   │   └── payment-processing/
│   │   │       ├── overview.md
│   │   │       └── api-contracts.md
│   │   └── architecture/
│   │       └── payment-flow.md
│   └── internal/
│       └── adr/
│           └── 0001-stripe-vs-braintree.md
└── config.json

Day 4-5: First Increment

# Team's first SpecWeave increment
/sw:increment "Add Apple Pay support"

# PM agent generates:
# ✅ spec.md with user stories
# ✅ plan.md with architecture
# ✅ tasks.md with test specs

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Week 3-4: Pilot Execution

Team Workflow

Morning standup:
/sw:progress
→ Shows: "3/8 tasks complete (37%)"

During development:
/sw:do
→ Implements task with AI assistance

End of day:
/sw:sync-progress
→ Updates JIRA automatically

Challenges Encountered

Challenge	Solution
"JIRA is source of truth" mindset	Showed how changes flow back to JIRA
Context explosion (large files)	Enabled chunked editing mode
Existing docs in Confluence	Imported critical docs, linked rest
Resistance from senior dev	Paired with them on increment

Results After 2 Weeks

Before SpecWeave:
- Feature spec: 2-3 meetings, vague outcome
- Implementation: Constant questions
- JIRA updates: Forgotten, stale
- Onboarding: "Ask Mike"

After SpecWeave:
- Feature spec: 30 min with AI + PM
- Implementation: Clear tasks, embedded tests
- JIRA updates: Automatic via hooks
- Onboarding: "Read the spec"

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Week 5-6: Team Expansion

Rollout to Teams 2-3

## User Service Team (6 devs)
- Day 1: Init + import existing docs
- Day 2-3: First increment
- Day 4-5: JIRA sync configured

## Web App Team (12 devs)
- Day 1: Init + architecture review
- Day 2-3: First increment (small feature)
- Day 4-5: Full team onboarding

Training Materials Created

Material	Purpose
10-min video	"SpecWeave in 10 Minutes"
Cheat sheet	Common commands
FAQ doc	Answers to frequent questions
Office hours	Weekly Q&A for first month

Common Questions

Q: Do I have to document everything? A: No. Start with active work. Historical docs can stay in Confluence.

Q: Does this replace JIRA? A: No. SpecWeave syncs TO JIRA. Stakeholders still use JIRA.

Q: What about existing tickets? A: Keep them. New work uses SpecWeave. Old tickets stay as-is.

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Week 7-8: Full Rollout

All 8 Teams Onboarded

Rollout timeline:
Week 5: Teams 2-3 (2 teams)
Week 6: Teams 4-5 (2 teams)
Week 7: Teams 6-7 (2 teams)
Week 8: Team 8 + cleanup (1 team)

Standardization

# .specweave/config.json (shared across repos)
{
  "sync": {
    "jira": {
      "enabled": true,
      "direction": "bidirectional",
      "updateOnTaskComplete": true
    },
    "github": {
      "enabled": true,
      "createIssues": true
    }
  },
  "quality": {
    "coverageThreshold": 80,
    "requireTests": true,
    "requireADR": true
  }
}

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Results: Before & After

Quantitative Metrics

Metric	Before	After	Change
Onboarding time	3 months	3 weeks	-83%
Requirements bugs	40% of total	12% of total	-70%
Time to first commit (new dev)	5 days	2 days	-60%
JIRA updates per feature	2-3 (manual)	8-10 (auto)	+300%
Spec quality (stakeholder rating)	3/10	8/10	+167%

Qualitative Feedback

From developers:

"I finally know what I'm supposed to build. The spec is right there."

From PM:

"JIRA updates itself now. I can focus on product, not status updates."

From tech lead:

"New hires read the docs instead of asking me 50 questions."

From VP Engineering:

"We shipped the Q4 roadmap on time for the first time in 3 years."

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Key Success Factors

1. Executive Sponsorship

✅ VP Engineering announced migration
✅ Time allocated for learning
✅ Success metrics defined upfront

2. Pilot-First Approach

✅ Started with ONE team
✅ Learned lessons before scaling
✅ Built internal champions

3. Not "All or Nothing"

✅ Historical docs stayed in Confluence
✅ Existing JIRA tickets untouched
✅ Gradual adoption, not big bang

4. Clear Value Proposition

✅ Solved real pain points
✅ Made developers' lives easier
✅ Reduced meetings, not added them

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Lessons Learned

What Worked

1. Quick wins first — Small feature, fast results
2. Champions on each team — Internal advocates
3. Async onboarding — Videos + docs, not meetings
4. JIRA integration early — Showed stakeholder value

What We'd Do Differently

1. Start with living docs — Should have imported architecture docs day 1
2. More ADR training — Teams didn't write ADRs at first
3. Clearer git workflow — Some confusion about branching
4. Earlier PM involvement — PMs joined late

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Migration Checklist

Use this checklist for your enterprise migration:

Phase 1: Preparation (Week 1)

• Executive sponsor identified
• Pilot team selected
• Pain points documented
• Success metrics defined

Phase 2: Pilot (Week 2-4)

• SpecWeave installed
• JIRA/GitHub integrated
• First increment completed
• Lessons documented

Phase 3: Expansion (Week 5-6)

• Training materials created
• Teams 2-3 onboarded
• Standards documented
• FAQ maintained

Phase 4: Full Rollout (Week 7-8)

• All teams onboarded
• Configuration standardized
• Metrics reviewed
• Continuous improvement started

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Related

• JIRA Migration Guide
• GitHub Migration Guide
• Brownfield Workflow