Overview

This workflow generates a consistent pipeline of qualified discovery calls through direct LinkedIn outreach targeting small business owners and agency operators who are at the edge of adopting AI but haven't built a system yet. The goal is 15–20 DMs per week using the Matt Lajakev three-stage formula, with every message sounding authentic and specific to the prospect.

Before You Start

Access to Thad's LinkedIn account via 1Password
Weekly tracker in Google Sheets (LinkedIn Outreach tab)
Google Doc for batching message drafts
Target profile criteria: 1–15 person teams, service businesses, tech-curious, 500–5,000 followers, US-based preferred
Templates A, B, and C ready for customization
Understanding of the three-stage formula: Connection → Value → Soft CTA

Steps

Pull prospect list of 15–20 people from LinkedIn search and content engagers, focusing on small business owners and agency operators who posted about AI in last 90 days
Add prospects to weekly tracker with Name, Company, LinkedIn URL, and template type designation
Draft all 15–20 DMs using Claude with prompt template and appropriate Template A (cold intro), B (post engagement), or C (warm lead) based on prospect context
Batch all drafted messages into single Google Doc organized by template type, marking uncertain messages with "[THAD REVIEW]"
Submit batch to Thad for review (all messages first 2 weeks, then first batch of Monday plus 3–5 spot-checks)
Send approved messages via Thad's LinkedIn account, updating tracker with Date Sent
Send follow-ups for prior week's DMs that haven't responded after 3+ days (Thursday activity)
Update tracker with Response, Response Type, and Next Step for all replies
Book discovery calls for interested prospects and flag complex conversations for Thad
Generate weekly metrics report using Claude from tracker data: DMs sent, responses received, calls booked, conversion rates

Quality Check

Every message references something specific about the prospect (not generic)
Messages follow three-stage formula: what you noticed → problem you solve → soft CTA
Tone sounds like Thad: conversational, direct, warm, no corporate speak
Messages are 3–5 sentences maximum
No links, no immediate pitch, no "I hope this finds you well" openers
Target benchmarks: 15–25% response rate, 5–10% positive response rate, 1–3 calls booked per week

Common Issues

Low response rates: Refine ICP targeting if below 10%, ensure messages are specific not generic
Messages sound too corporate: Use shorter sentences, honest curiosity instead of persuasion, avoid AI/consulting terminology in first message
Spam filter triggers: Never include links in first message, don't message immediately after connection acceptance
Template confusion: Use A for new connections, B for content engagement within 7 days, C for multiple touches or strong ICP match

LinkedIn DM Outreach Campaign