Sales / Sales Process

5 Tips You can Automate Your Cold Sales Email Outreach

Sujan Patel

Updated: Jun 01, 2020 · 7 min read

Toolkit for download in this article

A man reading his email on a laptop computer.

Automating your cold sales email outreach campaigns might seem like a godsend to time-strapped professionals, but you need to be careful when diving into the world of mail merges and automated rules.

Anand Sanwal, CEO and co-founder of CB Insights, learned this lesson firsthand when he analyzed 147 cold emails he’d received over a two-week span. Among his findings:

  • 93.9 percent of cold sales/prospecting emails were terrible
  • 88 percent used mail merge or copy/paste, and 77 percent of those had formatting issues
  • 76 percent of emails displayed zero knowledge of his business

Sure, “terrible” is subjective, but Sanwal’s experiences certainly point to the fact that automated sales emails are a tool that too many people are wielding clumsily. Want to get better results from your messages? Consider the following tips.

Want to get better results from your outreach emails? Consider these tips.

1. Test different subject line lengths

In late 2014, author Shane Snow and marketer Jon Youshaei set out to test what it took to get a cold outreach email opened. Together, they rounded up 1,000 email addresses from Fortune 500 and Inc 500 executives and sent messages asking what these busy professionals liked to see in cold emails.

After testing variables such as the use of “thank you” or the type of ask included, one of the biggest determinants they found in reply success was the length of the subject lines they used. The short subject line “Quick Question” received 66.7 percent of replies, relative to the 33.3 percent received for the longer subject, “15 Second Question for Research on Annoying Emails.”

Of course, as the team is quick to note, the relatively small number of responses received means these results aren’t statistically significant. The difference, however, is still worth noting and using to inform your own cold outreach efforts.

2. Automate in small batches

Today’s email automation programs like Keap can take a database of contacts and a template message and send it to hundreds or even thousands of people with the click of a single button.

And while this technology has the potential to significantly increase the efficiency of your outreach efforts, it’s worth remembering the wisdom of Spider-Man’s Uncle Ben: “With great power comes great responsibility.”

When you send to a broad batch of recipients, your message must be correspondingly wide-reaching to accommodate the needs of your full mailing list. And if you’ve ever been on the receiving end of such a generic, impersonal missive, you know it’s far less appealing than a message that’s been fine-tuned to your unique circumstances.

The answer isn’t to abandon automation entirely. While individually-personalized messages are nice, the limited number you can send out means you may miss some opportunities. Instead, automate in smaller batches by sending moderately-targeted message blocks to smaller groups of people.

For instance, you could email all of your sales leads in a certain geographic area with a message containing a comment on the local weather or sports team. You could follow up with speakers or attendees at a conference you recently traveled to with a note about your favorite sessions. In either case, you’re still sending more efficiently than you would be going one contact at a time, but you aren’t falling into the trap of overly-generic messages.

It’s a win-win.

3. Automate your follow up

In his CB Insights article referenced earlier, Sanwal goes on to lament the fact that, of all the messages he received, “Less than 20 percent of folks actually follow up with a second email.” That’s a pretty huge deal considering that, according to the Brevet Group, it takes an average of eight cold call attempts to reach a prospect, and that 80 percent of sales require five or more follow-up calls.

As depressing as these statistics may be, they represent an opportunity for savvy sellers. Regardless of who you’re emailing or what you’re asking for, your follow-up emails are probably going to be pretty similar and leveraging a tool like Keap can make this process easier. To keep things short and avoid annoying prospects, a sample follow-up email might look something like:

“Hey [name],

Just wanted to reach out again and see if you received my earlier message. I’d still love to set up a time to chat—can you please let me know when a good time to connect would be?”



That’s pretty generic, but your follow-up message isn’t the place for long personal appeals. What that means, though, is that—even if you personalize every aspect of your first message—you can still fully automate your follow-up process to send the same response to all of your prospects. Custom first messages; automated follow up. It’s the best of both worlds.

4. Automate regular email contacts

Alternatively, you can use this same process to initiate an automated series of regular email “touches” (think of this as marketing automation light, since you don’t need a full MA suite to pull it off).

For instance, marketer Neil Patel shares the idea of sending out a blog post email—as in, an update whenever you publish a new article. In particular, he highlights three benefits for doing so:

  • It provides a reason to reach out
  • It shows that you are interested in sharing information, not just making a sale
  • It proves your knowledge on a particular subject

This is another opportunity for automation that doesn’t require excessive personalization. Once your company has published a new blog post, you can send out an automated email blast stating that you thought of the recipient when the article went live.

If you want to get fancy, you could incorporate a merge field that pulls in information about the opportunity you want to discuss with the prospect. Now, rather than a generic blog post follow-up message, you could create something like:

“Hey [name],

Based on your interest in [our financial services offering], I thought you’d like to take a look at a recent blog post [our company] shared: “[blog post title]”

Hope you enjoy—would love to hear your thoughts on it!



You’ll need to tweak your wording so that all possible inputs to the merge field make sense, but once that’s done, you can use a template like this to reach a broad audience in an automated way.

5. Allow time to iterate your messages

Finally, when automating your cold email outreach, it can be tempting to take your huge database and send all your messages at once. But aside from the batch processing benefits described above, remember that sending smaller quantities over time gives you the opportunity to iterate different elements of your message.

Splinter off a small group, test a subject line and see what the response is. If you don’t get good results, you can try something different with the next batch because you haven’t already messaged them your first iteration.

All you need is a little time, patience and creativity, and you’ll be able to structure and send out automated email campaigns that your contacts actually want to open.


Sujan Patel is a leading expert in digital marketing. He is a hard working and high energy individual fueled by his passion to help people and solve problems. He is the co-founder of Web Profits, a growth marketing agency, and a partner in a handful of software companies including Mailshake,, Quuu, and Between his consulting practice and his software companies, Sujan’s goal is to help entrepreneurs and marketers scale their businesses. 

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