Write a LinkedIn outreach message that earns a reply before you ever pitch

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. My own relevant background or reason for reaching out: we both spoke at the same regional RevOps meetup last spring.

Write two messages, built to be sent days apart, not back to back.

1. CONNECTION NOTE — hard cap 300 characters, LinkedIn's platform limit for connection request notes, referencing commented on a post about RevOps teams drowning in disconnected spreadsheets specifically, with zero pitch anywhere in it. This message has exactly one job: be worth accepting. If you cannot reference commented on a post about RevOps teams drowning in disconnected spreadsheets specifically within the character limit without cutting it down to something generic, say so rather than quietly writing a note that only technically mentions it.

2. FIRST MESSAGE AFTER THEY ACCEPT — written as a separate follow-up sent after the connection is accepted, not immediately, and never in the same breath as the connection request itself. Lead with something genuinely useful, interesting, or specific tied to her comment specifically named the spreadsheet-reconciliation problem we solve — an observation, a question, a resource — before any mention of a RevOps reporting platform that unifies pipeline data across tools. If we both spoke at the same regional RevOps meetup last spring gives a real reason for the outreach beyond selling something, use it here; a rep with a genuine shared context has more room to be direct than one with none. If you cannot avoid the message feeling like a pitch given what's actually available, say so explicitly instead of forcing one in just to satisfy the structure.

TONE
Write both messages like a peer who did their homework, not a rep working a list. Ban "I came across your profile and was impressed by your experience" and any close variant of it — that exact phrase, or something functionally identical to it, appears in more automated LinkedIn outreach than any other single line, and it signals templated outreach within the first few words regardless of how personalized the rest of the message is. Ban exclamation points in both messages; enthusiasm punctuation reads as sales voice on a platform where the best-performing outreach reads like it was typed by a person, not scheduled by a sequence tool.

LENGTH
Connection note: one to two sentences, hard character cap as stated. Follow-up message: no more than four sentences, since a long first message after connecting reads as presumptuous before any real rapport exists.

CLOSING HONESTY CHECK
After both messages, state plainly whether commented on a post about RevOps teams drowning in disconnected spreadsheets is specific enough to justify the personalization used, or generic enough that a reader would recognize this as a templated message with a name swapped in — a signal like "works in your industry" or "has an impressive career" should be flagged as too weak to carry either message, even if the messages themselves read smoothly.