Sales From The Street-“Cold Emails & Curiosity" | Donald C. Kelly - 2028

Less than ten percent. That's how many highly targeted emails actually get opened. In this archive episode, pulled from an old Sales From the Street segment, I'm breaking down exactly what I look for in a cold email before I'll even open it, let alone reply. If email opens are a struggle for you right now, this one still holds up.

Why Most Cold Emails Never Get Opened

• People are buried in email. I was already at 67 messages by mid-morning when I recorded this, and I expected to hit 100 by the end of the day. Executives at bigger companies get even more.
• Less than ten percent of even a highly targeted email actually gets opened.
• If you want to land in that ten percent, everything starts with standing out immediately, not with writing a longer pitch.

Your Subject Line Has to Earn the Open

• The subject line is the first thing anyone sees, so it has to catch attention completely on its own.
• A common mistake, according to MailChimp, is a subject line that doesn't actually reflect what's in the email. Whatever you promise in the subject line has to match the message inside.
• The subject line also needs to spark curiosity instead of pitching outright. It should raise a question in the reader's mind that makes them want to open it.

Personalize the Subject Line With Real Research

• I referenced an example from Sales Hacker where a rep researched a prospect's Twitter, found out he was a Manchester United fan, and wrote the subject line, "Why a Man U fan is the best fit for sales enablement?"
• That kind of specific, researched detail makes a prospect stop and think the email is actually about them, not a mass blast.
• The goal is to find something real about the person, then build a question around it that gets them thinking before they've even opened the email.

Your Opening Line Has to Deliver on the Subject Line's Promise

• Once someone opens the email because of the subject line, the first sentence has to immediately pay that off.
• In the Manchester United example, the email opened by comparing Manchester United fans to sales enablement leaders, tying the personal hook directly into the pitch.
• Whatever personal detail earned the open needs to connect naturally to the product or service being pitched, right from the start.

Write Your Email Like the Letter F

• I picked this up from The Sales Development Playbook: structure the email so it looks like the letter F. A longer first line, a shorter second line, and lines that keep tapering down after that.
• Long emails are one of my biggest pet peeves, especially when people pitch me to be a podcast guest. I'm upfront about it: I won't read a long email, and it's likely to get deleted or ignored.
• Keeping an email close to the length of a text message makes it far more likely the prospect actually replies.

Keep the Call to Action Simple and Direct

• Every email needs a clear call to action that asks for a specific response, not something vague.
• Simple questions work best, like asking which day works best or whether the topic is something they'd be interested in.
• The easier the ask, the easier it is for the prospect to just hit reply, which is the entire goal of a cold email in the first place.

Skip the Fake Personalization

• I can spot a scraped, auto-generated email immediately. My LinkedIn profile reads "Donald C. Kelly," so any email that uses that exact version instead of how I'd actually be addressed gives itself away.
• Prospects notice the same thing. Sending "Hi Barbara S. Smith" instead of "Hi Barbara" is an instant tell that the email isn't personalized.
• Real personalization means using the way someone would actually be addressed, then tying the rest of the email back to something specific about them.

Tie Your Pitch to What Actually Matters to Them

• The best cold emails connect directly to whatever the recipient actually cares about. For me, that's downloads and value for my audience, so a strong podcast pitch speaks directly to that.
• Figure out the real business driver for the person you're emailing, then show how what you're offering moves that number, instead of just describing your product.
• Combine that with the F-shaped structure and a simple call to action, and the email does its one job: move the person to reply and take the next step.

"Keep it simple. The simpler it is, the better. The easier it is for me to hit reply and give you a quick answer, I'm game, and I'm all in it." — Donald C. Kelly

Resources

• Check out The Sales Development Playbook by Trish Bertuzzi, the book behind the F-shaped email structure.
• Join TSE Hustlers League this semester to improve your win rate and move deals through your pipeline.
• Visit Blue Mango Studios for help creating podcast production content.
• Join our LinkedIn cohort and learn to prospect the right way.

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.

1. This episode is brought to you in part by the TSE Sales Foundation.

Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey. We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and produced by Brightseed and Hill.