7 Painful Lessons I Learned From Cold Emailing 943 Companies

Forster Perelsztejn

June 22, 2023
cold emailing mistakes

If you're looking for a humbling experience, try cold emailing.

Even if you do it well and get results, it's a thankless job.

In world full of spam, setting your focus less than 100% on your prospect is useless

That being said, cold emailing is still widely used in most industries, with varying degrees of success.

If you're learning how to do this correctly, save yourselves some blunders.

Here's what I learned.

1. Nobody cares about your product

I'm sorry, I know it hurts.

But to be fair, you don't care about the people cold emailing you either.

The point is, you need to make your email about your prospect. Not about you, or your product.

If you're going to disrupt their day, you need to make it worth their while.

So, how do you do that?

Grab their attention

This might seem counterintuitive but don't introduce yourself.

Seriously, they don't know you, they don't care about you, and your name is already in the email anyway. Unless you're an authority and your name speaks for itself, don't introduce yourself.

Instead, grab their attention by mentioning something about their company. For example: "Congratulations on opening your new store!" or "It was great meeting you last year at the conference!" are great ways to catch a prospect's eye.

Cut to the chase

They're busy, so get right to it.

Don't even tell them "I know you're busy", you'd be wasting 5 words. Also, you're not asking for a favor, you want to solve something for them.

Let them know why you're writing, and why they're the right person to discuss that with you (unless it's obvious).

Don't mention your product just yet, tell when what you want to help them with, not what you want to sell them.

No one likes to be sold to.

Give clear and quantifiable benefits

You can't get them interested if you're being vague about what you're offering. Quantify it as much as you can.


"I saw 2 things on your website you should improve to get more conversions"

"We can help cut your accounting costs by 35%"

"I can help your pages rank 1st on SERPs in just 2 weeks."

Show some credentials

Even if you manage to keep them reading until this point, they still don't know you. And since they don't care, they're not gonna give you their time—or their money—because you sound nice.

You need to give them a reason to believe that you can actually help them. The best way to do that is by using social proof. Drop the names of some happy customers. The more relevant to them the better. Or write a line or two about a successful project they might relate to.

Have a clear call to action

If you're interrupting their day, you'd better make it easy for them to further the interaction.

Everything you've written up until this point is designed to get them to take action. Whether it is to respond to your email, click a link, download a document, your goal is to get them to act.

There are 3 things you need to keep in mind here:

- Only have 1 call to action. Each email needs to be focused on 1 specific goal. Why? Because if you ask too much, you're going to lose them. Also, you can only design content towards one goal at a time. One funnel can't lead into 2 buckets.

- Make it clear. Your prospect should immediately know what you expect from them. Make it clear and to the point.

- Make it easy to act on. If you want to set up a call, suggest some timeslots. If you want them to download something, send a direct link to the file. If you need information, send a form they can easily fill out.

This is not about you. It's all about them.

2. Subject line length is a myth

A lot of people will tell you that the optimal length for a subject line is about 35 characters. It's not too long, not too short, and it'll appear in full in your prospect's mailbox.

The truth is, it doesn't matter.

Not to say that medium-length doesn't work, but what matters most is specificity. You need to find something your audience responds to, whether it takes 7 or 67 characters.

The quality of your subject line determines your open rate. Take an adequate amount of time to perfect it.

3. Not automating is a waste of time

Personalizing your emails is absolutely necessary.

But it doesn't mean you have to do it all manually. The content of your message should vary, but the structure doesn't have to.

You can find efficient and affordable automation platforms that'll allow you to send multiple personalized emails at a time.

They'll allow you to follow-up at the right time, without having to lift a finger. You set it, and forget it.

Copying, pasting, and sending emails doesn't have any added value. You should be able to focus on having actual conversations. Let technology do the grunt work and use a sales automation platform.

Cold emailing is already hard as it is. Make things easier for yourself.

4. Automating wrong is a disaster

You should only start automating when you have a process in place.

Otherwise, you're just going to be automating something that doesn't work. It's going to be a waste of time and money for you, and you're going to make your prospects angry.

Also, make sure all the data is in the right place. I'm sure you've already gotten automated emails in which your name was missing or, worse, that said something like "Dear %FIRSTNAME%". That kinda breaks all illusion and makes you look like an amateur.

Take some time to review your list and make sure nothing's missing.

5. You need to follow up, a lot

If you think that most prospects will respond to your first email, you're kidding yourself.

Some will, but most responses come between the 3rd and the 5th email.

Persistence is key here, but you have to do it right.

Be assertive

Don't apologize, don't say you're "just checking in".

You're emailing your prospect because you're convinced you have value to offer them. If you're not, then don't contact them at all.

Instead, ask if they've got a chance to review your email, or how they'd like to proceed.

Provide value

If you're going to sending multiple emails, you don't want to keep asking if they've seen your message. Chances are they have but haven't deemed it worth it to respond.

You need to provide value that'll help them make a decision. It could be testimonials from companies from other companies in their industry. Or a data-backed report that proves that your methods are effective when it comes to their challenges.

Rule of thumb: your prospect should be better informed about their situation after reading your email.

Send a breakup email

Make it clear that the last email is the last email, and that you'd love to just know what could have changed their mind. Not because you want to improve your pitch, but because you want to improve your service.

They won't feel pressured, and it'll play upon their desire to help.

6. You want a response, not a sale

Don't try to sell, try to solve.

Aside from very rare cases, you won't convince a prospect to buy strictly from cold emailing.

It's only logical. If you're focused on selling your product, you're not focusing on solving your prospect's issues. And if you're not focusing on your prospect's issues, they won't care about your product.

Cold emailing isn't about selling. It's about starting a conversation.

7. Data isn't valid for long

People change jobs every few years nowadays.

You don't want to wait to start your campaign after gathering your data or a lot of it will be outdated by the time you use it.

This is also part of why you shouldn't be purchasing email lists, especially in dynamic environments.

If that didn't discourage you, you should now have a better idea of how to approach cold emailing.

And if anyone on your team is guilty of these, do them a favor and share this article with them!

About the author

Picture of the author: Forster Perelsztejn

Forster Perelsztejn is the head of marketing and customer acquisition at Rooftop. He has spent most of his career working in SaaS and creating content for a variety of authoritative publications. When he’s not working, you can find him playing music, taking photos, and taking care of his pets.

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