I love emails that tell a story. Messages that weave every detail into a satisfying and entertaining read. Uncommon Goods is one of my favorite storytellers, and now online sharing, storage, and file management company, Hightail, is quickly becoming another.

They’ve mastered providing a unique combination of compelling imagery and clever messaging. Their emails are so good, in fact, that I’ve saved all (yes ALL) of the emails I’ve received from them over the past several months so I can track their consistency. The verdict? They’re pretty darn consistent.

So let’s take a look at one of my favorites from them—a Get Smart-inspired email, below:



1)  Strong subject line and headline: “Ensure your sensitive files are only seen by private eyes” and “For your eyes only.” I’m intrigued. Intrigued enough to a) open the email and b) click through. Each piece of copy plays off of the other and inspires an action.

Hightail always picks a fun theme for their messages and maintains it throughout their subject lines, headlines, body copy, and imagery. They are subtle storytellers who prove that when you pick a theme, you should stick with it. (Note the cheeky “PS” at the close of the email below the social promo.) Hightail realizes that creating an experience for the reader fosters engagement…and (especially in my case) loyalty.

2)  Re-instate value prop of email message: To continue their consistent messaging, Hightail does something I really like—they include a small call out on the top right hand side of every email that summarizes the purpose of their email. In this case, it’s “Confirm their identity to control your files.” 7 quick words that sum up the entire email. It’s a nice shout out to all the tl;dr (too long, didn’t read) fans out there.

3)  Visible unsubscribe(s): Hightail includes not one, but two unsubscribe opportunities in their email. One in the top “nav bar” and another in the footer. Well done. With these two unsubscribes, Hightail makes it clear that they’re serious about only sending mail to those who want to receive it. By setting this precedent, they’re building trust with their engaged users…and gratitude from those who wish to unsubscribe.

4)  Permission reminder: Quintin from our compliance team wrote a nice article about the importance of permission reminders not too long ago. Give it a look and then see Hightail’s no nonsense example:

This message was sent to you because you opted-in to receive Hightail product news and special offers.

5)  Effective CTA: A marketing email is nothing without a call to action. Hightail’s copy effectively communicates that they take security seriously and highlights what steps they take to ensure it. With this information, they’ve armed their readers to confidently “send a file now.” Their CTA is straight to the point, prominent, and aligned with the messaging in the email.

6)  Upsell: Hightail subtlety upsells their Professional plan in the closing of their email as a secondary CTA. Never waste an opportunity to show your customers opportunity for added value—just do it respectfully and keep it relevant. Hightail does just that.

In sum, Hightail delivers a stellar email that tells a complete story from start to finish and provides:

  • Consistent design
  • Compelling content
  • Strong CTAs
  • CAN-SPAM Compliance

Nicely done!

For more examples of emails that inspire us and for tips on how to make your email copy more effective, download our free guide: Transactional and Marketing Email: How to Build a Powerful Integrated Email Program

*image via collider.com

Jillian Smith
As Twilio SendGrid's Sr. Director of Content, Jillian is responsible for ensuring that SendGrid provides valuable thought leadership content through the blog, whitepapers, webcasts, and more. When not writing and editing, you can find Jillian frequenting Denver restaurants in search of the best queso.