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The Ultimate Cold Email Checklist For 2018

Forster Perelsztejn author on Overloop the sales engagement, cold email, and LinkedIn automation software blog
Forster Perelsztejn Dec 26, 201710 min read

Writing great cold emails is simple, but no one said it was easy. Well, I'll make it easy for you with this ultimate cold email checklist for 2018!

Ready to nail those cold emails the Overloop way?

1. Subject line

Your subject line makes all the difference when it comes to email opens, which is why it's at the top of this cold email checklist.

Short or Specialized

There are two schools when it comes to subject lines: short and specialized.

It is usually recommended to write short subject lines so as to let it appear fully, especially on mobile devices.

That being said, a long headline that won't appear fully on mobile might still raise interest if the copy is specialized enough to encourage the recipient to read further.

According to data we've been collecting; subject lines between 100 et 102 characters yield 50% to 70% open rates.

That being said, very short subject lines have given us tremendous results as well.

To the point

Let them understand what's inside the message; it should be clear from the beginning.


Stay classy, avoid ALL CAPS, exclamation points !!!! and $$$$ signs

Not spammy-looking

Even though SPAM trigger words are all about context, be careful not abusing them, they could get you trashed or blacklisted real fast.

2. Sender settings

It doesn't only matter what you send; how you send matters as well.

Professional email adress

It's always better to use a company domain, it'll make you look more professional. Also, simple Gmail or Outlook (or better yet, AOL accounts) will look fishy to ESP's if you cold email a lot of people.

Trustworthy email address

It's not enough to use your domain. I mean, would you open an email from or

Go for or even

Also, it could cause deliverability issues since mailbox providers don’t just evaluate the IP and domain, they also put the From field under scrutiny.

Adequate username

If you get an email from Google and another from Larry at Google, which one are you most likely to open? Think about what your reader would rather see.

3. Keep it short

They don’t know you, and they’re probably busy.

Be smart, don’t waste their time with a foot-long page of information, you’ll have all the time to discuss that further down the road. For now, it’s all about getting attention and curiosity.

If you met that person in real life, you’d introduce yourself, tell them how you know about them, get to the point and probably exchange business cards. Use the same approach in your cold email. Be natural.

Attention grabbing

DO mention something about them, their company, their industry that has good reason to catch their attention.

If you start by introducing yourself, saying that you work at that company they've never heard of and presenting a product they don't care about at that point, you've probably already lost.

The goal of every sentence must be to get your recipient to read the next one, and then the next one, and so on.

So unless you’re someone very famous and important, like Elon Musk or Beyoncé, stating your name and the company you work for -which are in your sender field, email address and your signature anyway- doesn’t make me want to keep reading.

Reason for reaching out to them

Get to the point, quickly. If you have a message, it should be laid out as soon as you have your prospect's attention.

Reason for reaching out to them

It's not enough to state your purpose, show you've done your research by making clear why you've reached out to that person specifically, why you believe they're the appropriate person to talk to.

Clear benefit

Stating that you believe your product can benefit them won't cut it. Find out what difficulties and challenges your prospect is or may be experiencing and get into that.


Again, they don't know, so you need to build trust. Usually, dropping names of happy customers from their industry does it; the trick.

Call to action

This is one of the most crucial elements of this cold email checklist.

The goal, the very purpose of your email, is to get me to take action to make the sales process move forward. Which means everything you write in the email must be directed towards that one and only purpose: the action. Which implies a few things.

Only one CTA

If you ask your prospects to do several different things, you'll lose them. Focus on the single one action that'll move the process forward.

Dare to ask

If you legitimately believe that you can offer true value to your prospect, then there's no reason not to dare make an ask. If you don't believe in it, why should your prospect?

Make it easy

Make sure that, whatever you ask, it's easy for the prospect to do. Avoid having them fill out forms or give complex answers. Try instead getting them on the phone, having them download a piece of content…

4. Don't be a sales person

No one likes a sales person. Okay, I'm kidding, but really, nobody likes to be sold to. Start the conversation like a business conversation, not like a sales pitch.

Minimize the details

No one cares about your product. What people do care about, is their pain points; your product only enters the stage as a solution to those pain points. So, yes, tell the what it is you do, but keep the details to a minimum.

Focus on the prospect's challenges

Not only should you keep details to a minimum, they must also be directly relevant to your prospect's challenges. Do you know what pains they could be experiencing? If not, go back to doing some research!

5. Personalization

Personalization is the key, it's easy to see if you've put in the effort of doing your research of if you're just mass sending a template.

Do your research

Have you spent at least a few minutes collecting relevant information about your prospect? Collect data about their industry, company size, competitors, location, content they've published…


Segment your prospects into smaller relevant lists that could benefit from the same message/added value. For example, a CFO at a big company and a startup founder may both be in your target market but won't necessarily benefit from your product in the same way.

Mention something specific

After researching your prospects and segmenting your lists, use the info you've collected to grab their attention. Mention an event they've attended, content they've put out, a recent fundraising…

6. Links

Feel free to include links, just follow these best practices.

Only one link

Keep it to one link so as not to seem spammy and avoid multiple calls to action.

Don't mask links

Don't display a URL that's actually leading to another one -like this if spam filters don't catch you, your recipient will definitely be suspicious.

Reputable domains only

Only link to reputable domains or you risk ending up in the spam folder.

No URL shorteners

Shortened URL's are notoriously used by spammers who try to hide malicious link behind type links. If it's a matter of tracking, add tags that you can track in Google Analytics instead.

7. Follow up

Based on data we've collected, more than 70% of answers come from the 2nd to 4th email of the sequence; don't miss out on that!

Be assertive

Don't just "check in" or "touch base". It makes you come across as shy and unfocused. If your job is to make the sales easy for the prospect, you should be asking where the situation’s at and how they’d like to move further.

Don't put the prospect on a pedestal, this a business conversation, from equal to equal.

No repetition

Include your previous email in the follow-up message so as not to repeat yourself. This'll give you the opportunity of giving more/new information and bring additional value (see next point).

Bring additional value

You rarely ever convince a prospect to buy on the first email; in a way, you shouldn't try to outright sell on the first touch and instead try to build a relationship based on trust and credibility. Which is why the following three might be useful, as they show that other customers successfully faced the same issue, ideally with measurable results.

Case studies

They're an in depth description of how a specific customer overcame a challenge thanks to your product. Tease a case study in your email thanks to a success story or a referral.

Success stories

Don't sell, tell a story, a success story preferably so as to overcome your prospect's objection story!


Ask customers to put in a good word for you. If they're relevant to your prospect, it might resonate with them.

Read more about bringing value to sales/marketing emails in this article on the Datanyze blog.

8. Deliverability

A lot of what we already covered makes sure you don't end up in the SPAM folder. Here are a few more technical steps you should take to make sure your emails get where they're supposed to go.

Reliable ESP

The reliability of an E-mail Service Provider depends on the reputation of the IP addresses and domains of their clients. If you communicate through a shady ESP, you’ll be associated with shady IP’s and domains and your e-mails will more than likely end up in junk folders.

For that instance, we strongly recommend using the paid version of Gmail in G suite. Let’s just say that Google’s reputation is, you know, pretty good.

DNS records setting

These are more technical interventions but they can heavily improve your cold email deliverability.


To make it simple, your SPF defines which IP addresses can be used to send emails from your domain, which can be useful when you deliver emails through a sales automation platform.

Servers are like messengers, passing on mail from you to your recipient. By setting your SPF -which can only be done from your own domain- your sending server can prove to your recipient’s receiving server that you gave it permission to transmit an email on your behalf. If you don’t, it could make emails bounce back.

We, here at Overloop -as well as most of our clients- deliver emails through Google’s servers; so here are their instructions on how to set your SPF.

It’s unfortunately impossible to make a step-by-step guide for DNS settings since the process depends on every domain host. Here are, nonetheless the link to the instructions for some of the most popular ones:


Much like SPF, DKIM is a way to identify you as the real sender of the email. It works as some kind of seal.

You’re actually setting up two keys:

  • private one, which is encrypted, unique to your domain, only available to you and which you use to encrypt your signature in the header of your emails
  • public one, which you add to your DNS records using DKIM standard to allow your recipient’s server retrieve it and decrypt your hidden signature from the header of your email

Again, if you’re using Google, heres their guide. For the rest, it depends on your domain host.


Spam checker

Before sending your e-mail, take a minute to get it through a spam checker like It’s free and it will test your e-mail for the main liabilities that could impair its efficiency. It’s an easy way to avoid the spam folder, use it.

It won’t however tell you if your IP is blacklisted; in that case, you should check MXToolbox.

Email validity

People tend to change jobs on a regular basis, so their email addresses tend to disappear. To prove this point Radius ran an experiment: they looked at what happened over a 4-month period in 2016 (May to August) to 10.000 CRM contacts. When the experiment ended: 7,57% of the entries had become invalid; the person had moved to another job or was no longer be reachable.

This is a problem because when your bounce rate rises above the 10% threshold, you’re almost guaranteed to start ending up on blacklists.

Use an email validity checker tool to make sure your data is up to date.


Unless you absolutely have to, don’t attach files to your e-mails, especially if they’re unsolicited. And if you do, avoid large files at all cost. They’re yet another obvious red flag for spam filters. This is the reason why Overloop doesn’t allow you to attach files directly to your emails.

What you can however do is upload the files to a cloud service like Dropbox or Google Drive and share the link in your email. The reputability of these services won’t hurt your deliverability.

How guilty are you?

It's okay, I didn't know all of that hen I started out. No excuses now though, tick every box!