Quick-Start Execution Checklist: Insurance Broker Campaign

Campaign: Insurance Broker Lead Intake Automation
Target: $50 M -$ 100M revenue brokerages
Last updated: 2026-02-04

This is your go-to execution checklist. Use this to launch the campaign in the next 48 hours.

PRE-LAUNCH (Do this first)

Setup & Research

Read the campaign brief — insurance-broker-lead-intake.md
Review research insights — insurance-broker-research-insights.md
Study custom outreach messages — insurance-broker-custom-outreach-top5.md
Set gate date in campaign brief (2 weeks from today)
Assign brief owner in campaign brief

Tools

HeyReach account set up and configured
HubSpot ready for logging contacts and outcomes
LinkedIn profile optimized (headline, summary mention insurance automation)
Clay (optional) for enrichment if needed

WEEK 1: TOP 5 NAMED ACCOUNTS (Custom Outreach)

Day 1-2: LinkedIn Research & Connection Requests (Decision-Makers)

For EACH of the Top 5 firms, identify and connect with decision-maker:

1. SHEPHERD INSURANCE (~$74M, Carmel, IN)

LinkedIn search: “Shepherd Insurance” + (“Head of Operations” OR “COO” OR “VP Operations”)
Save profile URL to spreadsheet/HubSpot
Send connection request using Message Option A from custom outreach doc
Log in HubSpot: Company: Shepherd Insurance, Contact: [Name], Status: Connection Sent, Date: [Today]

2. SCOTT INSURANCE (~ $69 M -$ 99M, Lynchburg, VA)

LinkedIn search: “Scott Insurance” + “Lynchburg” + (“VP Surety” OR “Head of Surety” OR “CFO”)
Save profile URL
Send connection request using Message Option A (20-hour WIP hook)
Log in HubSpot

3. STARKWEATHER & SHEPLEY (~ $78 M -$ 91M, East Providence, RI)

LinkedIn search: “Starkweather & Shepley” + (“SVP Operations” OR “Enterprise Architect” OR “COO”)
Identify the SVP who gave the “spreadsheets and PDFs” quote (research LinkedIn/company blog)
Save profile URL
Send connection request using Message Option A (spreadsheet fatigue hook)
Log in HubSpot

4. HOUCHENS INSURANCE GROUP (~$72M, Bowling Green, KY)

LinkedIn search: “Houchens Insurance Group” + (“Head of Operations” OR “COO” OR “Sarah Walden”)
Sarah Walden = Senior Application Technician (key contact from research)
Save profile URLs (both ops leader AND Sarah if possible)
Send connection request to ops leader (failed automation hook)
Log in HubSpot

5. BOWEN, MICLETTE & BRITT (~ $61 M -$ 86M, Houston, TX)

LinkedIn search: “Bowen Miclette Britt” + (“Head of Operations” OR “COO”)
Save profile URL
Send connection request using Message Option A (assembly line inefficiency)
Log in HubSpot

Day 3-5: LinkedIn Research & Connection Requests (Hiring Managers)

For EACH of the Top 5 firms, identify and connect with hiring manager:

Find Hiring Managers

LinkedIn Jobs search: “[Company Name] Underwriting Assistant” OR “Intake Coordinator” OR “Processing Specialist”
Identify hiring manager (usually posted by recruiter or hiring manager’s name in job description)
Alternative: Search company employees with title “Talent Acquisition” or “Recruiting” or “HR Manager”

Send Connection Requests (Multi-Threading)

Shepherd Insurance — Hiring manager for Personal Lines Account Manager
- Use Message Option B (hiring manager angle) from custom outreach doc
- Log in HubSpot (note: this is 2nd contact at same company)
Scott Insurance — Hiring manager for Intake Coordinator or Production Underwriting Assistant
- Use Message Option B
- Log in HubSpot
Starkweather & Shepley — Hiring manager for Commercial Underwriting Assistant
- Use custom message referencing “hiring armies of Assistants while SVP wants to stop dealing with spreadsheets”
- Log in HubSpot
Houchens Insurance Group — Hiring manager for COBRA Processor
- Use custom message referencing “hiring for rules-based task that should be automated”
- Log in HubSpot
Bowen, Miclette & Britt — Hiring manager for Placement Specialist
- Use Message Option B
- Log in HubSpot

Day 6-7: Monitor Connections & Prepare Follow-Ups

Check LinkedIn for accepted connection requests
Update HubSpot status: “Connection Sent” → “Connected” (with date)
Prepare follow-up messages for each connected contact (copy from custom outreach doc, personalize with their name)
Set reminders for Day 8-12 (send follow-up 5-7 days after connection)

WEEK 2: FOLLOW-UP MESSAGES & REMAINING 10 ACCOUNTS

Day 8-12: Send Follow-Up Messages (Top 5)

For EACH connected contact, send follow-up DM:

Update HubSpot after each message:

Status: “Connected” → “Follow-up Sent”
Log date and message option used

Day 10-15: Load Remaining 10 into HeyReach (Templated Sequence)

Remaining 10 accounts:

Marshall & Sterling (~$87M, Poughkeepsie, NY)
Sterling Seacrest Pritchard (~$86M, Atlanta, GA)
Premier Group Insurance (~$85M, Greenwood Village, CO)
Oakbridge Insurance (~$78M, LaGrange, GA)
Lawley Insurance (~$74M, Buffalo, NY)
Robertson Ryan Insurance (~$71M, Milwaukee, WI)
Towne Insurance (~$90M, Norfolk, VA)
Christensen Group (~ $50 M -$ 100M, Eden Prairie, MN)
The Mahoney Group (~ $50 M -$ 70M, Mesa, AZ)
Turner Surety & Brokerage (~$51M, Saddle Brook, NJ)

HeyReach Campaign Setup

Create new campaign in HeyReach: “Insurance Broker Lead Intake - Templated”
Upload list (CSV with Company, LinkedIn URL, Name, Title for each contact)
Build sequence:
- Step 1: Connection request (choose from Message Library based on profile)
- Step 2: Follow-up message (5-7 days delay, choose from Message Library)
- Step 3: (Optional) ROI/qualification message (on reply)

Selection Logic (Per Account)

Turner Surety → ROI-focused, reference WIP bottleneck (like Scott)
Christensen Group → Tech buyer angle (“saw you partner with ePayPolicy”)
The Mahoney Group → Innovation angle (“saw you joined BrokerTech Ventures”)
Sterling Seacrest, Lawley → Construction angle (speed + quality trade-off)
Towne, Oakbridge, Marshall & Sterling → Scale/volume angle (manual work doesn’t scale)
Premier Group, Robertson Ryan → Standard pain (intake lag, manual work)

Launch Templated Sequence

Activate campaign in HeyReach
Monitor daily for responses
Log outcomes to HubSpot (connected, replied, interested, not interested)

WEEK 2-4: CONTENT ROLLOUT

Content Drafting (Use Robert GPT)

Draft Posts 1-6 (core content) using outlines from campaign brief
- Use content/cc-content-system/robert-gpt/memory/examples/linkedin/FORMAT_INDEX.md
- Output in Campaign Post Template
- Load into Notion content calendar
Draft Posts 7-10 (niche content) using outlines from campaign brief
- POST 7: Why your LLM pilot failed
- POST 8: The 20-hour report costing $50K/year
- POST 9: Hired Architect but team lives in spreadsheets
- POST 10: Hiring “Intake Coordinators” = treating symptom

Content Publishing Schedule

Week 2:

POST 1 (Mon/Tue) — Why intake takes a full day (general problem)
POST 7 (Thu/Fri) — Why your LLM pilot failed (Shepherd, AI skeptics)

Week 3:

POST 2 (Mon/Tue) — Adding headcount doesn’t fix intake
POST 8 (Thu/Fri) — The 20-hour report (Scott, surety firms)

Week 4:

POST 3 (Mon/Tue) — Messy docs → cited risk profiles (solution)
POST 9 (Thu/Fri) — Hired Architect but team lives in spreadsheets (Starkweather)

Week 5: (If campaign extends)

POST 4 — Speed vs quality trade-off
POST 10 — Hiring Intake Coordinators = treating symptom

Content Amplification

Tag relevant companies in posts (if appropriate and not overly aggressive)
Send DM to prospects referencing relevant post: “Just wrote this about your exact situation — thought you might find it interesting. [Link]”
Monitor engagement from ICP personas (likes/comments from Ops leaders, Surety VPs, etc.)

ONGOING: RESPONSE HANDLING & PIPELINE MANAGEMENT

When They Reply (Scripts in Custom Outreach Doc)

“We already tried automation” → Acknowledge LLM failure, differentiate (task-specific, cited)
“No budget right now” → ROI reframe (you’re hiring $50K assistants; we eliminate those roles)
“Send me more info” → Send one-pager, push for 15-min demo with sample data
“Who else are you working with?” → Pilot partners, offer design partner role

Demo Booking

Offer 15-minute demo with their actual data (sample lead, WIP report, Excel schedule)
Use Calendly link or manual scheduling
Prep demo based on their pain point:
- Shepherd → Show deterministic extraction with citations
- Scott → Show WIP report automation (20 hours → 20 minutes)
- Starkweather → Show spreadsheet-to-structured-data ingestion
- Houchens → Show commission reconciliation parsing
- BMB → Show API submission workflow

HubSpot Pipeline Stages

GATE CHECKPOINT (2 Weeks from Launch)

Review Gate Criteria

3 SOWs created and sent?
1 signed contract secured?
5 customers attracted to a meeting (demo)?

Update Campaign Brief

Fill out SOW & meeting tracking table (§1)
Update gate decision (§7): Go / Conditional Go / No-Go
Add notes on what’s working / what’s not

Learnings to Document

Did “LLM failure” acknowledgement resonate or trigger defensiveness?
Did quantified pain points (20-hour WIP, $75K/year) accelerate conversations?
Did hiring managers respond to outreach?
Did multi-threading (ops leader + hiring manager) yield better results?
Did pilot pricing drive urgency?
Which of the Top 5 had highest engagement?
Which content posts (7-10) drove the most conversation?

DAILY CHECKLIST (Once Campaign is Live)

Morning (15 min)

Check LinkedIn for connection acceptances
Check LinkedIn for DM replies
Update HubSpot statuses
Respond to interested prospects (within 24 hours)

Afternoon (15 min)

Send follow-up messages (if 5-7 days have passed since connection)
Send any scheduled demos prep (sample data from their industry)
Check HeyReach campaign performance (templated sequence)

End of Week (30 min)

Review pipeline in HubSpot
Calculate metrics:
- Connection acceptance rate (Top 5 vs Templated)
- Reply rate (decision-makers vs hiring managers)
- Demo booking rate
- SOW sent / signed
Update campaign brief tracking table
Adjust messaging if needed (if response rate < 20%, revisit hooks)

RESOURCES

QUICK WINS (Do These First)

If you’re overwhelmed, start here:

This Week:

Day 1: Connect with decision-makers at Shepherd and Scott (Top 2 accounts with clearest pain)
Day 3: Connect with hiring managers at Shepherd and Scott
Day 8: Send follow-up messages to Shepherd and Scott (if connected)
Week 2: Draft and publish POST 7 (LLM failure) and POST 8 (20-hour WIP)

Why These 2?

Shepherd: Failed LLM pilot = highest readiness, clearest differentiation
Scott: 20-hour WIP = most quantified ROI, easiest to demo

If you land 1 of these 2, the campaign is a success.

Ready to launch? Start with Day 1 checklist above. Good luck! 🚀

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