Everything you need
to know before sending
your first cold email
Helping you ensure maximum deliverability and reach more prospects!
Standing out in a prospect’s inbox is difficult enough of a task, but losing a good percentage of your outreach to spam is the kiss of death for cold email campaign results.
Success begins before the first email is ever sent.
Now here’s the ultimate checklist you need to follow before you send your first cold email.
1. Never ever use your own domain
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Not setting up a new domain for cold email is the same as not having car insurance: it’s fine until you find yourself in an accident.
In the land of cold email, this would translate into having your entire company’s domain blacklisted: all your emails are sending fine until nothing is being delivered.
Experience has taught us that people starting with cold email outreach often make mistakes that get them in trouble and it’s too risky to jeopardize your primary professional domain.
So now what? It is time to create a new domain, something domain adjacent.
If your company domain is company.com, you could try something like getcompany.com. Other popular choices are .net, .io and .co (although .co will need stronger inbox warming).
Like when trying anything new, it’s best to have some safeguards, and a new cold email domain is something every cold emailer needs.
2. Never use a free email account for cold outreach
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Free email accounts are very tempting because, well, they are FREE!
Free Gmail (@gmail.com) or Outlook… these accounts might have better deliverability in general, BUT there is a catch.
Free email accounts are blocked quickly when a mistake is made, with no possibility of re-opening them.
Using professional accounts like Google Workspace, get you access to business support to assist with any issues concerning blocked accounts that usually can be resolved within 24 hours.
3. Use Outlook/Office 365 as an email provider for best deliverability
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Over the last several years our team has tested many email providers and the winner for best email provided in terms of deliverability is…Office 365. Although Office 365 can be difficult to use, it works.
We recommend creating a professional business email account with them and using an inbox warm up tool, like Warmup Inbox to get them firing on all cylinders.
Although, Google Workspace is much easier to use and their integrations are stellar: Sending follow-ups will increase your volume quickly, so do plan that in advance.
By default, all new Google Workspace accounts are limited to 500 emails per day until you reach $30 in billing.
Pro-tip: Pre-pay $30 to unlock 2,000/day to avoid bounces from Gmail when your volume increases with follow-up.
4. Be sure your SPF and DKIM are set for your domain
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Protect yourself against spoofing & phishing, and help prevent your outreach emails marked as spam.
You’ll go straight to the junk folder if you don’t.
SPF with Office 365
DKIM with Office 365
SPF with Google Workspace
DKIM with Google Workspace
5. Always check your deliverability
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Before sending an email, first check out the spammy-ness of your email content.
The simplest way to test is by using services like mail-tester.com to determine your deliverability score. Mail-tester will analyze your message, your mail server, your sending IP… and show you a detailed report of what’s configured properly and what’s not.
Then look at how it can be improved by addressing all of their recommendations.
6. Your Inbox needs Warming
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You’ve created a new domain, tested your email content, followed the previous steps and are ready to send, right? Nope, not quite yet. Time to warm that cold inbox up!
Servers know when a new domain is cold and doesn’t have any history of safe sending or receiving traffic.
This is a red flag that can lead to getting spam blocked and quickly burning that new domain you worked so hard to set up.
Use an Inbox Warmer, like Warmup Inbox, to warm up your inbox before and during campaigns.
Using an Inbox Warmer, your email account will automatically send emails to a network of real people inboxes talking to each other. Your emails will be opened, and some of them will be replied to. This positive engagement will result in higher deliverability for your outreach campaigns.
Sales teams have reported seeing a ~20% increase in open rates just from using an inbox warmer.
7. Always verify your email list prior to sending
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You can set up everything correctly and take every precaution but if your list is junk, so are your results.
It is priority #1 to make sure the email addresses on your list won’t bounce. Google and other mail providers will block your account quickly. Remember…Bounce = spammer. So make sure all your emails are verified.
Never buy lists without verifying, and make sure you always use services like BriteVerify or Neverbounce to clear your list first.
8. Avoid similar email content
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Creating emails with similar content can get flagged as spam. Use custom attributes and dynamic tags to make sure each email is unique. Create a few different email variations (like A/B testing)… this will also allow you to measure what content is resonating best with your audience.
9. Spread out or Delay message sending
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Spread out your email spending. Don’t fire off all your emails in one shot.
Space out your emails by a few seconds to match more normal sending practices and behaviors. By default we like to space out emails by 30 seconds (you can always increase this number).
10. Don’t add images in the first email
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Keep imaging out of your first touch emails, if you can avoid it.
Your first emails should be fairly short, so adding an image has a bad text-to-image ratio, and spam filters don’t like that.
Tracking pixels (to determine open rate) are the same as images too. To increase deliverability, you should consider disabling the tracking of opens in the first message. That will help your initial email get into their inbox and greatly increase delivery of future emails.
Once follow-ups kick in, there will be enough text to add images back in – so that the ratio won’t be an issue.
11. No more than 1 link per email, and don’t mask links
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If you track links, make sure they’re not coming from a shortening service (e.g Bit.ly).
Those are likely to be listed in spam lists already. Spammers use these link shortening techniques all the time, and you don’t want to be lumped in with the spammers.
Either write the URL without making a clickable link or disable click tracking in the first message. For example: upsidesales.com (see, it’s not a clickable link, yet Gmail will transform this into a clickable link for you)
12. Don’t contact more than 50 people/day
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If you do it right, you can get around a 25% – 35% reply rate.
No need to max out Gmail’s limit.
It’s hard to find 2k valid emails that won’t bounce each day.
Let’s face it…without using a team, like Upside, to do outreach at scale, you don’t have the bandwidth to seriously engage with 400 replies anyway.
Don’t go for quantity, as you’ll be punished in many ways. Try to nail the quality down with low volume first. Then build in some automation to handle the wave of follow up that comes next…
13. Avoid unusual bursts of emails
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Firing off most of your emails in a day is bad for both the front end and back end of your outreach efforts.
On the front end your first touch emails will hurt your reputation score, get a larger percentage spam blocked, and hurt future deliverability. On the back end you’ll end up with a sea of follow up that will be unmanageable.
It’s way better to send 50 emails each day, than to send 250 emails one day a week.
Spam filters pay attention to things that are out of the ordinary. So to fly under the radar, you need to have a steady and continuous amount of emails sent daily rather than a one-time event that may be caught.
14. Only send to individual contacts
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Make sure your lists contain individual contact emails. Don’t send emails to groups such as marketing@, info@, sales@ … if you do, you’ll run the chance of getting flagged as a spammer.
15. Send to business emails, not personal emails
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Personal emails addressed with business activities lead to greater spam complaints, which will impact your deliverability over time.
So, avoid @yahoo.com, @gmail.com, and other free types of emails, as they are more likely to be personal emails and not business emails. That won’t lead to new business
anyways.
16. Relationship before revenue
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Don’t sell on the first email.
Remember that the goal of cold emails is to engage in a conversation, get a person to raise their hand, and hopefully have a meeting with you. Not to get a sale from the first email. It’s best to sell only once you’ve created a relationship; not before.
People who try to sell right away get flagged as spam super fast, and future emails will end up in junk folders.
A simple rule…relationship before revenue.
17. Don’t repeat yourself in a follow-up
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Be sure not to repeat yourself…be sure not to repeat yourself.
Include the previous email for context, and provide a different call to action. Remember to always add new value with each follow-up.
If you ask to connect in the first email, ask if they already have a solution in place on your second email. Keep it original.
18. Write as if it was text only
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It’s not a beauty contest. People buy people so write like a human. No highlighting, no color, no bullet points, bold text, or custom fonts… resist the urge! Your reply rates will thank you and you’ll improve email deliverability.
