How NOT To Write a Prospecting Email, Part IV

Today’s winner comes from a popular marketing software company. 3 elements distinguish it for our education purposes: The subject line, an image and humor.

Element 1: Clever subject line.

Subject: Not ANOTHER generic Dreamforce meeting request

I am so conflicted about this subject line. On the one hand, it’s really funny, because the largest sales-marketing conference in the world does generate a ton of emails from hungry prospectors who attack the attendee list in order to set up swanky San Francisco wine-and-dining to win your business.

Initial grade: B+. This is clever humor. I like the use of capitalization, too … the emphasis is appropriate. The hint of mystery is also effective, leaving the reader to wonder: What makes this request different?

Ultimate grade: F, upon reading the message and learning that Mr. Eager Marketing Software Company Sales Rep assumed I was going to the premier conference known as Dreamforce. Nice try, but I’m not. (Thanks for rubbing it in, buddy.) What could have prompted him to think that I am? Did I go last year? Negative. In fact, I went two years ago … learned a lot, had some memorable late-night experiences with my colleagues at Jack in the Box (don’t ask: What happens in San Fran stays in San Fran).

Element 2: $50 bills, y’all.

Okay, you think you know where this is going … a $50 incentive. If only this email were so ordinary: No, it includes an image of what appears to be a stack of $50 bills. That’s right, an image of some cash money smack in the middle of the email, as item #2 in a numbered list, no less. In fact, it’s the entirety of his second reason to meet. Although, to quibble, this image really belongs in the third reason, the “$50 Most Wanted bounty,” because it simply illustrates the bounty, not a separate reason to meet. (Few things are more precious than space in a cold email, meaning the less of it you use, the better.)

email_generic DF request

Grade: B, because I can’t stop smiling. The logical part of my brain tells me A.) It’s crazy to use images in this kind of cold email because they’re usually blocked by email clients like Outlook, which would be the dominant client among this B2B audience and B.) Trying to buy random prospects’ attention is usually not the best path to ideal long-term clients. However, my inner child loves this image because its inclusion is so goofy. The stolid bearded face of former U.S. president Ulysses S. Grant is the last thing I expected to see in this email. I have to think Mr. Eager Marketing Software Company Sales Rep was aware of the humor and decided to insert this image with tongue firmly in cheek, which I can appreciate. (I’m giving him credit regardless of his intentions.) Which brings us straight to element 3 …

Element 3: Humor. Aside from the $50 bill, there are other touches of humor sprinkled throughout. The 4th reason he lists for meeting him at Dreamforce, a “therapy session” for “commiserating about all of the terrible Dreamforce meeting invites” is actually really funny.

Grade: A-. This is one of the more noteworthy prospecting emails I’ve actually read where the humor worked. A lot of outbound hustlers try to be funny, but often come off cheesy, self-absorbed or just plain creepy (see the online dating-inspired “Let’s do lunch” and other suggestively worded email subject lines from women senders to men).

Other thoughts

Great job with the personalization, but Mr. Eager Marketing Software Company Sales Rep betrayed his secret automation weapon (or lack of proofreading) when he left a space between my boldface name and the question mark in the first line (see image above, circled in red). In fact, the boldface helps call attention to the error, which is probably not what the professional salesperson intends. This means that #1, the personal touch is obviously machine-created (i.e., not friendly) and #2, the secret automation weapon (i.e., CRM or marketing automation platform) is broken or the sender is careless because he didn’t take the time to fix this simple, yet unmistakable error. And this glaring typo immediately kills what might otherwise be a charming message to somebody actually attending Dreamforce.

Overall grade: D.

The only thing preventing this message from an ‘F’ grade was the humor. Evaluating on humor alone, we’d have a passing mark, maybe even the start of a new series about brilliant prospecting email diamonds in the outbound rough. But you need more than humor to sell most business prospects, which is ultimately why I this message must be rated near a complete failure.

Thanks, Mr. Eager Marketing Software Company Sales Rep, for inspiring the latest in my ongoing series looking at bad prospecting emails. For other popular miscues deconstructed, check out:

Paul Richlovsky

About Paul Richlovsky

Paul brings a writing and teaching background to his decade-long marketing career. He advises clients on content strategy and editorial direction. He is an enthusiastic marketing automation practitioner and active member of the Cleveland Marketo User Group. He has written/edited multiple marketing guides, including those aimed at healthcare, higher education, financial services, B2C brands and manufacturing audiences. With a BA in English from the College of Wooster, he is also the author of a collection of poetry, "Under the Lunar Neon."He is particularly interested in usability, digital governance, ballroom dancing, bachata, racquet sports, and romping with his niece and nephews.

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