How to Craft Context-First Messaging That Drives Replies

Most outreach today still feels lazy. Dropping a prospect’s name or title might look like personalization, but it doesn’t show you actually understand them and modern buyers tune it out instantly.

Tom Alaimo will show you how to move beyond surface-level touches to outreach that feels earned. You’ll learn how to spot the difference between basic personalization and true relevance, and how to lead with context that matters: recent company moves, industry shifts, or public signals that make your message stick.

Tom will also share his simple framework for context-first messaging, along with real examples across email, LinkedIn, and voicemail.

If your prospecting feels ignored, this show will give you the structure and inspiration to craft messages that connect and convert.

What You'll Learn:

• Why surface-level personalization falls flat in today’s market
• How to turn contextual insights into messaging that earns attention
• A repeatable framework for writing context-first outreach across channels