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exitfive Newsletter #161

Exit Five Newsletter: Direct Mail Strategies

July 10, 2025
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Hello and welcome to the Exit Five Weekly Newsletter — read by 42,000 B2B marketing professionals around the world. Exit Five is a membership site designed to help you build a successful career in B2B marketing. Join 5,700 other members at exitfive.com.

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ChatGPT, Perplexity, Google AI Overviews. These are the new gatekeepers of brand visibility and if you’re not showing up in their answers, you’re invisible.

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With 63% of websites already getting traffic from AI search, this isn’t the “future of SEO.” It’s happening now.

Find out where you stand in AI search and how to get ahead.

📬 Must-Try Direct Mail Strategies They’ll Actually Remember

Direct Mail Strategies Graphic

You're drowning in a sea of generic LinkedIn messages and ignored cold emails.

Your open rates are plummeting. Your prospects aren't responding.

8 years ago, Kris Rudeegraap was a sales rep at Talkdesk facing the same problem. Email was getting spammy. Inboxes were impossible to crack.

So he got creative. He started writing handwritten notes. Sending Amazon chew toys when he heard dogs barking on calls. Operating like a mini mail room in his office.

It worked so well that he thought: "There's got to be a platform to automate this."

There wasn't. So he built one.

Here's what Kris has learned building a $100M direct mail company:

Finding the Perfect Gift

Most marketers guess what to send. Kris uses data.

His "Smart Send" feature analyzes recipient behavior and suggests the perfect gift:

  • Boston prospects get Dunkin' Donuts
  • Paris prospects get macaroons
  • New parents get diapers (the ultimate win)

What to try: Research your prospect's recent posts, location, and interests before sending anything. One personalized gift beats 100 generic ones.

Know Where to Send

Kris's team knows whether to send gifts to your home or office using:

  • IP data tracking
  • LinkedIn content analysis
  • Office proximity mapping

They'll send cookies to your house if you work remote, or surprise you at the office if you commute.

What to try: Check LinkedIn for "WFH" mentions, recent office photos, or commute complaints. Adjust delivery accordingly.

Make Unboxing Part of the Experience

Kris's biggest pet peeve? Boxes stuffed with zigzag filler for one tiny mug.

His solution: Focus on the unboxing experience, not just the gift.

What to try: Test your packaging. If opening it feels like work, redesign it. Simple beats fancy every time.

Make it Personal

Instead of generic "hope this finds you well" messages, Kris's team uses AI to craft personalized notes based on:

  • Recent podcast appearances
  • Company news
  • Industry trends
  • Personal interests

What to try: Spend 2 minutes researching before writing. Reference something specific they've said or done recently.

Timing is Everything

Don't send randomly. Kris automates sends based on:

  • CRM triggers (deal stage changes)
  • Intent data (website visits)
  • Behavioral signals (email opens)

What to try: Set up 3 automated triggers in your CRM. When someone hits a specific stage, the gift goes out automatically.

The bottom line? Direct mail works when it's thoughtful, not expensive.

A $12 bag of cookies delivered at the right moment beats a $100 branded speaker that collects dust.

Make it personal. Make it timely. Make it memorable.

📺 UPCOMING EVENTS

Exit Five Pro Members Only

  • July 11th: Non-SaaS Marketing Meetup: How to Master B2B Virtual Events
  • July 22nd: 3 Smart Ways Marketers Are Actually Using AI
  • July 23rd: Women in B2B: Setting Boundaries and Expectations, Professionally and Respectfully

CMO Club Members Only

  • TODAY: AMA about ABM with Mason Cosby, CEO & Founder of Scrappy ABM
  • July 31st: AI Spotlight - How Are B2B Marketing Leaders Using AI?

Not a member yet? Learn more about an Exit Five Membership here.

If you are an Exit Five member, click here to RSVP to these events.

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