Insurance Content - Visual Roadmap
┌─────────────────────────────────────────────────────────────────────────┐
│ INSURANCE CONTENT WEEK OF FEB 17-21 │
│ Ready-to-Execute System ✅ │
└─────────────────────────────────────────────────────────────────────────┘
📍 START HERE → INSURANCE_CONTENT_README.md
↓
┌───────┴────────┐
│ │
PLANNING EXECUTING
↓ ↓
┏━━━━━━━━━━━━━━━━━━━━━━━━┓ ┏━━━━━━━━━━━━━━━━━━━━━━━━┓
┃ PLANNING (Mon Feb 17) ┃ ┃ EXECUTING (Tue-Fri) ┃
┣━━━━━━━━━━━━━━━━━━━━━━━━┫ ┣━━━━━━━━━━━━━━━━━━━━━━━━┫
┃ ┃ ┃ ┃
┃ 1. Read Main Plan ┃ ┃ 1. Publish Daily Post ┃
┃ ↓ ┃ ┃ ↓ ┃
┃ 2. Review POST 7 Draft ┃ ┃ 2. Monitor Engagement ┃
┃ ↓ ┃ ┃ ↓ ┃
┃ 3. Draft Posts 8-10 ┃ ┃ 3. Respond to Comments ┃
┃ ↓ ┃ ┃ ↓ ┃
┃ 4. Schedule Posts ┃ ┃ 4. Move to DMs ┃
┃ ┃ ┃ ↓ ┃
┃ Time: 2 hours ┃ ┃ 5. Log in HubSpot ┃
┃ ┃ ┃ ┃
┃ ┃ ┃ Time: 2 hrs/day ┃
┗━━━━━━━━━━━━━━━━━━━━━━━━┛ ┗━━━━━━━━━━━━━━━━━━━━━━━━┛
📅 WEEK AT A GLANCE
MON 2/17 │ TUE 2/18 │ WED 2/19 │ THU 2/20 │ FRI 2/21
──────────┼───────────────┼───────────────┼──────────────────┼────────────────
│ │ │ │
PLANNING │ POST 7 │ POST 8 │ POST 9 │ POST 10
│ ✅ DRAFTED │ 📝 OUTLINE │ 📝 OUTLINE │ 📝 OUTLINE
│ │ │ │
• Read │ "Why Your │ "The 20-Hour │ "Architect + │ "Hiring
Plans │ LLM Pilot │ Report │ Assistants │ Coordinators
│ Failed" │ ($75K/yr)" │ Paradox" │ = Symptom"
• Review │ │ │ │
POST 7 │ Target: │ Target: │ Target: │ Target:
│ Shepherd │ Scott │ Starkweather │ All hiring
• Draft │ (failed AI) │ (surety) │ (digital trans) │ managers
8-10 │ │ │ │
│ 10 AM EST │ 10 AM EST │ 10 AM EST │ 11 AM EST
• Setup │ │ │ │
Tracker │ Engage │ Engage │ Engage │ Engage
│ 2-4 hrs │ 2-4 hrs │ 2-4 hrs │ 2-4 hrs
2 hours │ │ │ │
│ │ │ │ EOD REVIEW
🎯 THE 4 POSTS
┌──────────────────────────────────────────────────────────────────┐
│ POST 7 │ Why Your LLM Pilot Failed (and What Works) │
├────────┼──────────────────────────────────────────────────────┤
│ When │ Tuesday, Feb 18, 10 AM EST │
│ Target │ Shepherd Insurance, AI skeptics │
│ Hook │ "You rejected it for the right reason" │
│ Status │ ✅ FULL DRAFT READY │
│ File │ drafts/2026-02-18-insurance-llm-failure-uttam.md │
└────────┴──────────────────────────────────────────────────────┘
┌──────────────────────────────────────────────────────────────────┐
│ POST 8 │ The 20-Hour Report Costing $50K/Year │
├────────┼──────────────────────────────────────────────────────┤
│ When │ Wednesday, Feb 19, 10 AM EST │
│ Target │ Scott Insurance, surety firms │
│ Hook │ "$75,000 a year on one task" │
│ Status │ 📝 OUTLINE READY (in main plan) │
│ Draft │ Use POST 7 as template │
└────────┴──────────────────────────────────────────────────────┘
┌──────────────────────────────────────────────────────────────────┐
│ POST 9 │ Hired Architect but Team Lives in Spreadsheets │
├────────┼──────────────────────────────────────────────────────┤
│ When │ Thursday, Feb 20, 10 AM EST │
│ Target │ Starkweather & Shepley, transformation firms │
│ Hook │ "The $50M-$100M scaling paradox" │
│ Status │ 📝 OUTLINE READY (in main plan) │
│ Draft │ Use POST 7 as template │
└────────┴──────────────────────────────────────────────────────┘
┌──────────────────────────────────────────────────────────────────┐
│ POST 10│ Hiring "Intake Coordinators" = Treating Symptom │
├────────┼──────────────────────────────────────────────────────┤
│ When │ Friday, Feb 21, 11 AM EST │
│ Target │ All hiring managers, ops leaders │
│ Hook │ "Human middleware" │
│ Status │ 📝 OUTLINE READY (in main plan) │
│ Draft │ Use POST 7 as template │
└────────┴──────────────────────────────────────────────────────┘
📚 YOUR DOCUMENTS
┌──────────────────────┐
│ README (Start Here) │
└──────────┬───────────┘
│
┌───────────────┼───────────────┐
↓ ↓ ↓
┌──────────────┐ ┌────────────┐ ┌─────────────┐
│ Main Plan │ │ Quick Ref │ │ Tracking │
│ (70 pages) │ │ (1 page) │ │ (Checklist) │
└──────┬───────┘ └────────────┘ └─────────────┘
│
↓
┌─────────────┐
│ POST 7 │
│ (READY!) │
└─────────────┘
File Structure:
./
│
├── 📋 INSURANCE_CONTENT_README.md ← START HERE
│ (Navigation, quick start, FAQs)
│
├── 📖 INSURANCE_CONTENT_WEEK_FEB17.md ← Main Plan
│ (Full outlines, narratives, strategy)
│
├── 📄 INSURANCE_CONTENT_QUICK_REF.md ← One-Pager
│ (Key messaging, DM usage)
│
├── ✅ INSURANCE_CONTENT_TRACKING_FEB17.md ← Tracker
│ (Daily checklists, metrics logging)
│
├── 📊 INSURANCE_CONTENT_SUMMARY.md ← What We Built
│ (Overview of deliverables)
│
├── 🗺️ INSURANCE_CONTENT_VISUAL_ROADMAP.md ← This File
│ (Visual guide)
│
└── drafts/
└── 2026-02-18-insurance-llm-failure-uttam.md ← POST 7 ✅
(Full draft, ready to publish)
🚀 GETTING STARTED (5 MINUTES)
┌─────────────────────────────────────────────────────────────┐
│ STEP 1: Open README │
│ ↓ │
│ STEP 2: Read "Getting Started" section │
│ ↓ │
│ STEP 3: Review POST 7 draft (already done!) │
│ ↓ │
│ STEP 4: Open Tracking doc, start checking boxes │
│ ↓ │
│ READY TO EXECUTE! 🎉 │
└─────────────────────────────────────────────────────────────┘
📍 CAMPAIGN ALIGNMENT
┌───────────────────────────────────────────────────────────────┐
│ INSURANCE CAMPAIGN │
│ (Insurance Broker Lead Intake Automation) │
├───────────────────────────────────────────────────────────────┤
│ │
│ TARGET: $50M-$100M revenue brokerages │
│ Complex risks (surety, construction, captives) │
│ │
│ TOP 5 ACCOUNTS: │
│ 1. Shepherd Insurance (~$74M) → POST 7 │
│ 2. Scott Insurance (~$69-99M) → POST 8 │
│ 3. Starkweather & Shepley (~$78-91M) → POST 9 │
│ 4. Houchens Insurance (~$72M) │
│ 5. Bowen, Miclette & Britt (~$61-86M) │
│ │
│ CAMPAIGN GOALS (2-week gate): │
│ • 3 SOWs sent │
│ • 1 signed contract │
│ • 5 meetings booked │
│ │
│ CONTENT'S ROLE: │
│ ✓ Build credibility │
│ ✓ Support outreach │
│ ✓ Create conversation starters │
│ ✓ Drive inbound interest │
│ │
└───────────────────────────────────────────────────────────────┘
✅ SUCCESS METRICS
GOOD WEEK │ GREAT WEEK
────────────────────────────┼──────────────────────────────
✅ 4 posts published │ ✅ All of "Good Week" PLUS:
✅ 50+ total comments │ ✅ 1+ meeting booked
✅ 5+ quality ICP comments │ ✅ 1+ SOW sent
✅ 3-5 DMs started │ ✅ Top 5 account engaging
✅ Posts in 5+ outreach DMs │ ✅ Posts shared by ICP
💡 PRO TIPS
┏━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━┓
┃ 1. POST 7 IS READY → Just review and publish Tuesday ┃
┃ ┃
┃ 2. Use POST 7 as template for Posts 8-10 ┃
┃ Same structure: Hook → Body → CTA ┃
┃ ┃
┃ 3. Respond to comments FAST (within 2-4 hours) ┃
┃ Engagement drops sharply after 4 hours ┃
┃ ┃
┃ 4. Use posts in DMs: "Wrote this about [pain]: [link]" ┃
┃ Lead with value, not pitch ┃
┃ ┃
┃ 5. If Top 5 account comments → prioritize immediately ┃
┃ Public comment + DM follow-up ┃
┗━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━┛
🎯 QUICK ACTIONS
→ Need Overview? Open INSURANCE_CONTENT_README.md
→ Need Quick Ref? Open INSURANCE_CONTENT_QUICK_REF.md
→ Drafting Posts? Use INSURANCE_CONTENT_WEEK_FEB17.md
→ Tracking Progress? Open INSURANCE_CONTENT_TRACKING_FEB17.md
→ Publishing Tuesday? Review 2026-02-18-insurance-llm-failure-uttam.md
🎬 NEXT STEPS
NOW (5 min) → Open README, review POST 7 draft
TODAY (2 hrs) → Draft Posts 8-10 using outlines
MONDAY (1 hr) → Final review, schedule posts
TUESDAY-FRIDAY → Execute, engage, track
RESULT: 4 high-quality posts supporting insurance campaign 🎯
Summary: Everything is ready. POST 7 fully drafted. Outlines for Posts 8-10 complete. Tracking system in place. Just review and execute.
Start here: INSURANCE_CONTENT_README.md