Verified against ChatGPT · 2026-08-06
Write a LinkedIn outreach message that earns a reply before you ever pitch
Build a two-touch LinkedIn sequence — a connection note under the platform's 300-character limit and a value-first follow-up — using specific profile signals instead of a recycled connection request.
The prompt
Ready to copy — highlighted parts are example details you can swap.
I want to reach out to Anjali Rao, Head of Revenue Operations at Wayfinder Analytics, on LinkedIn. Here's what's actually on their profile or recent activity: commented on a post about RevOps teams drowning in disconnected spreadsheets. What we do: a RevOps reporting platform that unifies pipeline data across tools. The reason I think this is relevant to them specifically: her comment specifically named the spreadsheet-reconciliation problem we solve. Write two messages: 1. CONNECTION NOTE — under 300 characters (LinkedIn's hard limit), referencing commented on a post about RevOps teams drowning in disconnected spreadsheets specifically, with zero pitch. This message's only job is to be worth accepting. 2. FIRST MESSAGE AFTER THEY ACCEPT — sent as a follow-up, not immediately after connecting. Lead with something genuinely useful or interesting tied to her comment specifically named the spreadsheet-reconciliation problem we solve — a specific observation, question, or resource — before any mention of a RevOps reporting platform that unifies pipeline data across tools. If you can't avoid pitching in this message without it feeling hollow, say so instead of forcing a pitch in. Tone: like a peer who did their homework, not a rep working a list. No "I came across your profile and was impressed by your experience" — that line shows up in more automated outreach than any other and reads as exactly that. After both messages, tell me honestly whether commented on a post about RevOps teams drowning in disconnected spreadsheets is specific enough to justify personalization, or generic enough that this will read like a templated message with a name swapped in.
Customize the highlighted detailsoptional — the prompt above already works
Why this works
LinkedIn actually caps connection request notes at 300 characters, so writing to that constraint from the start avoids drafting a message that gets silently truncated on send. Splitting into two touches reflects a real product-behavior pattern: pitching inside the connection note itself tends to lower accept rates, so delaying any ask to a second message sent after acceptance is a widely taught LinkedIn prospecting sequence rather than an arbitrary structure. Banning "I came across your profile and was impressed by your experience" targets the single most overused line in automated LinkedIn outreach — one that signals mail-merge to a recipient within the first few words, no matter how personalized the rest of the message is.
What you get back
Connection note (187 chars): "Anjali — your comment about RevOps teams drowning in spreadsheet reconciliation hit close to home, that's the exact problem we spend our days on. Would love to connect."
Verified against
ChatGPT GPT-5.1 · 2026-08-06
Claude Sonnet 4.5 · 2026-08-06
Changelog
- 2026-08-06 — Initial version, verified against GPT-5.1 and Claude Sonnet 4.5.
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