Session 5 - Linkedin Outreach Playbook

Pre Read Content
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Hand Out Content
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LinkedIn automation workflow showing connection request sequence, follow-ups, message timing, and branching based on acceptance or reply

Step 1

The core Idea- Create an Eco-chamber on LinkedIn

Step 2: Target Account List

Stop fishing in empty ponds - target accounts that are actually ready to buy

First principles LinkedIn outreach strategy including ICP definition, buyer targeting, developer nurturing, and intent-based messaging
Content strategy diagram showing overlap between struggling sales reps and stalled prospects resulting in high-converting content

Step 3: Account Research

Stop researching every account individually - find the patterns

Example of personalized LinkedIn outreach message for DevTools highlighting intent signals, competitor awareness, and value proposition
LinkedIn outreach benchmarks showing connection acceptance rate, response rate, positive replies, meetings booked, and conversion rates

Step 4: Finding Economic Buyers & Connecting on LinkedIn

Connecting with the people who actually own budgets

LinkedIn account warming checklist including daily connection limits, profile optimization, content posting, and cleanup strategy
Two-pronged GTM strategy showing top-down sales targeting buyers and bottom-up developer relations building product adoption
Example of account segmentation for API monitoring DevTool using enterprise size, fintech industry, and reliability use case

Step 5: Messaging

Messaging, Follow-ups and advanced tactics that turn connections into meetings booked

Key account research dimensions for DevTools including industry, use cases, and company size with messaging implications

Landing page we built for LangChain

https://youtu.be/wzmvvHDa9wM?si=YPG4BNik17d7xSja

Weekly account assignment workflow using ICP, intent signals, and sales-ready filters to generate outreach target lists

https://www.youtube.com/watch?v=rZou1biB8WI&t=912s

Unstructured-Loveable 10 (1).pdf

Account list strategy showing difference between master ICP account list and in-market high-intent accounts for sales outreach

Unstructured.io’s playbook for converting free OSS users into enterprise customers starts with a simple, personalized LinkedIn message:

“Hey {Name}, thank you for using our Unstructured open source. You’re a valued customer. Here is a landing page that is going to show you your usage.”

And the second follow-up message builds on that with more insight:

“Hey {Name}, based on your product usage signals, here’s how many {X no. of hours} we estimate your engineers are spending trying to build your own solution.

That translates to approximately {$$ money value} in engineering time.

Would you be interested in discussing this further?”

Step 6: LinkedIn  Automations

LinkedIn profile optimization checklist including headline, summary, skills, experience, keywords, and content strategy tips
6-step LinkedIn outbound framework covering profile optimization, targeting, research, messaging, and automation

Full Playbook:

https://www.reo.dev/resources/linkedin-outreach-playbook