How to do LinkedIn Outreach with AI

Warm up prospects, start conversations, and convert connections without being a pest.

Make sure to replace the BRACKETED INFORMATION before use.

LinkedIn connection request messages

For: GTM Team · Solo Founder · Growth

Write 5 LinkedIn connection request messages for [PRODUCT] targeting [ICP].

Character limit: 300 chars max. Each for a different scenario:

1. After engaging with their content — you commented/liked something they posted

2. Shared community/event — you’re both in the same Slack group, attended same conference

3. Mutual connection — you have a shared connection you can mention

4. Triggered by their news — they got promoted, raised funding, published something

5. Cold, no context — honest and direct with a clear reason for connecting

Rules:

– No “I’d love to add you to my network”

– No immediate pitching

– Sound like a human, not a sales tool

– Include one genuine, specific observation about them

After the templates, give 3 rules for what NOT to do on LinkedIn outreach.

DM conversation sequence

For: GTM Team · Growth

Write a LinkedIn DM sequence targeting [ICP] for [PRODUCT]. I want to start a conversation, not blast a pitch.

Message 1 — Day 1 after connecting:

– Acknowledge the connection, ask a genuine question relevant to their work (NO pitch)

– 3 sentences max

Message 2 — Day 5 (if no reply):

– Share a relevant resource, article, or insight — still no ask

– 3 sentences max

Message 3 — Day 12 (value + soft ask):

– Connect a pain point to what we do, suggest a quick call or share a case study

– 4 sentences max

Message 4 — Day 20 (break-up):

– Honest, light close — permission to say no

– 2 sentences max

Also write:

– 3 engagement tactics to warm them up BEFORE sending any DM

– One “trigger event” to watch for that makes outreach 3x more likely to get a response

LinkedIn comment strategy

For: Solo Founder · Growth

I want to use LinkedIn comments as a top-of-funnel strategy to get on the radar of [ICP] without sending cold DMs.

Help me build a commenting system:

1. Target account list — what criteria should I use to identify 30–50 accounts to follow and engage?

2. Comment frameworks — write 5 comment templates for different post types:

   – Industry opinion post

   – A win/case study share

   – A question/poll post

   – A controversial take

   – A personal story post

3. Rules of good commenting — what makes a comment get noticed vs. get scrolled past?

4. Cadence — how many comments per day, for how long before a DM makes sense?

5. Tracking — simple way to track who I’ve engaged with and when

Goal: turn strangers into warm prospects who recognise my name before I ever DM them.

LinkedIn profile optimisation brief

For: Solo Founder

Rewrite my LinkedIn profile to attract inbound interest from [ICP]. My current profile:

– Headline: [CURRENT HEADLINE]

– About section: [CURRENT ABOUT]

– Recent posts or content themes: [DESCRIBE]

My goal: [e.g. attract founders to book demos / get recruited as an advisor / build an audience of CMOs]

Rewrite:

1. Headline (220 chars max) — benefit-driven, not just title. Include who I help and how.

2. About section (600 words max) — story arc: who I help, the problem I solve, how, proof, CTA

3. Featured section — 3 content types to pin (with a brief description of each)

4. Experience bullets — rewrite 2–3 bullets for my current role to sound outcome-focused

5. CTA — clear next step at the end of the about section

6. Keywords — 10 keywords to weave in naturally for LinkedIn search

Make it sound like a human wrote it, not a resume bot.