How to automate outreach personalization with AI

What counts as a reason to reach out?

Asking for “personalization” produces compliments.

Ask for evidence of a trigger instead, and allow the companion to come back with nothing.

Prompt: “For outreach research, these are the only things I count as a real hook, in priority order: they’re hiring for a role that implies the problem we solve, they shipped or announced something in the last 60 days, someone senior there said something public about this problem, or they just raised. Company size and industry are not hooks. If none of these exist for a prospect, tell me. I’d rather skip them than send a weak line.”

Research the list, hooks only

Sixty companies, four sources each, three new columns. No copy yet.

Prompt: “Take the 60 companies in the ‘Q3 outbound’ sheet. For each, spend a few minutes across their careers page, LinkedIn posts from the last 60 days, their blog or changelog, and any recent news. Add three columns: the hook, the URL where you found it, and how strong it is: strong, thin, or none. Don’t write any copy yet.”

Read that column before drafting starts. If 40 of 60 come back ‘none’, the target list is the problem, and you learn it now rather than from a 0.4% reply rate.

Draft from the hook, in your voice

Companions learn your writing style from the outreach you have already sent, so point at your best sent folder and name the phrases you hate.

Prompt: “For the ‘strong’ hooks only, draft a first email each. Structure: one sentence on the specific thing you found and why it made me write, one sentence on what we do for companies in that exact situation, one question that’s easy to answer. Under 90 words. Ban: ‘I hope this finds you well’, ‘quick question’, ‘circling back’, ‘love what you’re building’, and any sentence about their impressive growth. Match the tone of the five sent emails in my Gmail folder ‘Best outbound’. Queue everything as drafts. Send nothing.”

How many drafts should you read before approving 60?

Ten. Correct the pattern rather than the instance, and the correction carries forward.

Prompt: “Show me ten drafts. Do any two open the same way? If so, rewrite the openers so no two emails in the batch share a structure.”

Two prospects who compare notes should not find the same sentence.

When does a follow-up earn its place?

When it carries something new. The companion re-checks the company before it writes one.

Prompt: “Five business days after each send with no reply, check whether anything new happened at that company: a post, a hire, an announcement. If yes, draft a follow-up built on that new thing. If nothing new happened, draft a two-line nudge that adds one useful specific, not a bump. Queue both kinds for approval.”

That is the sales prospecting loop end to end, with a person at exactly one point: the point where sending happens.

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