Raise your hand if you’re sick of the debate over whether cold-calling is dead or not. All of you? Great! Me too.

As for whether social selling is taking over, well, let’s just say I have a few thoughts to share on this as well.

Buckle up for my mini-rant.

The debate is bullshit. To be successful in sales, you need to use all of the tools available to you. This means the phone, social media and email. They’re all valuable.

But before I praise the virtues of email and talk about how you can write killer emails at scale, I want to stress one thing first.

You cannot sell over email.

There, I’ve said it. So, you might ask, why am I writing this post?

Great question.

Email is still an incredibly valuable means to engage people, especially when you are trying to secure a first meeting. The challenge is that it’s a crowded marketplace with a lot of noise.

The rest of this article will unpack the tools, traps, best practice and strategies for scaling outbound sales emails.

After all, email use around the world continues to skyrocket. By the end of 2019, the number of worldwide email users will be over 2.9 billion. That’s over one-third of the world’s population! Can you afford not to be reaching them?

Before we get into how to write killer outbound emails, there are a couple of things that I’d like to address. First of all, technology.

The hidden trap of tracking tools

In recent years, there has been an explosion of data tools that allow people to scale and measure the effectiveness of their emails.

There are tools that provide you with lists of accurate data like Clearbit, Datanyze, ContactOut and DiscoveryOrg.

There are also outbound email automation tools like Outreach, SalesLoft, Yesware, ToutApp, PersistIQ and more that enable you to send multiple emails and measure the results.

The combination of these two technologies has enabled many sales people to become more efficient and more effective at creating first meetings.

Unfortunately though, these high-powered tools are also being used by lazy reps to send more crap emails out to uninterested people. These reps are sending out poorly executed emails at scale which are burning the quality leads in their territory and teaching our customers to ignore sales emails.

Still, there is some good news to come out of that.

The amount of crap emails people receive make the truly good ones stand out.

So, what constitutes a good email? Well, that brings me to my second point.

Relevance trumps personalisation every time

It’s no longer enough to insert {First Name} into your mail merge template or tool, and assume you have personalised your message enough for the recipient to think you care.

As Teddy Roosevelt once said, “Nobody cares how much you know, until they know how much you care.”

The key to showing someone that you care is making your email relevant.


Look closely at that definition. Notice the words ‘connected’, ‘appropriate’ and ‘considered’? It tells you what all emails should be. Which brings me to my next point.

What should you include in an outbound email?

There is a basic structure you should follow to get the most out of an outbound sales email.

Songs, movies, books… what do they all have in common?

They have a storyline.

So too should an email.

The proper structure of an outbound email consists of the three R’s:


R: Relevance

Which consists of research and reference;


An opening line that shows you have done your homework, and indicates this is not, strictly speaking, a COLD call. Think back to Teddy Roosevelt’s quote, and show that you truly care and that the recipient is not just a number.


A reference to another customer who has had a similar situation or experience. This shows the recipient they are not alone in what they are going through, and that they might be missing out on a potential gain. The psychology of ‘keeping up with the Joneses’ is famous for a reason!

R: Reward

There is an old saying that you have to give to get, and this holds true in email marketing. If you offer someone value, such as a link to valuable insights or a relevant blog post, they will start seeing you as a resource who understands what is directly relevant to them. They will be more open to meeting as a consequence.

R: Request

Lastly, you need to ensure that you have made a request. Too many emails these days simply fade into the finish line without giving the reader an action to deliver on. What’s the point of writing killer content if you don’t ask them to engage? I am not talking about going straight in for the kill, but you can drop a few breadcrumbs by offering to share additional insights or requesting their perspective on the reward you sent them.

Here are some other best practices.

Do’s and Don’ts of outbound sales emails

  • DO Keep it short. Half as long; twice as powerful.
  • DO Optimize content for mobile phones. Make effective use of the subject line and the first 50 characters.
  • DON’T Start with “Hi my name is … and I work for…” Get to the point!
  • DON’T Start your opening sentence with “I”. Make it about them, not you.
  • DO Be careful how you lead into your Reference story. Talk about “How Customer X and Y experienced great Benefit A and great Benefit B”, not “Our service offers great Feature A, B and C.”
  • DO Offer relevant links and industry insights.
  • DON’T Include attachments — always link to content.
  • DO Use a person’s first name to draw their attention to a key point.
  • DO Close with something social that communicates or relates.
  • DON’T Try to close by pushing for a meeting — your primary goal is to gauge interest.

Now that you know the basic structure, we can begin the process.

3 failsafe steps to scale killer sales emails

One question I often get asked is, if I write one killer email, will that be enough?

The short answer is no.

With today’s crowded inboxes, there is a very high chance that your first, third or even fifth email is never read.

Heather Morgan from SalesFolk, who creates email campaigns for hundreds and hundreds of companies, says that the statistics show that at least one third of all email responses come from the fifth or seventh email received.

So if you’re out there thinking you can get away with only writing one killer email, you’re not approaching this with the right attitude.

You need to be building campaigns or an email series with a minimum of 6, preferably 8–10 call-outs.

When I tell people this, they are often concerned.

“Won’t I piss them off if I send them that many emails?”

If you’re sending crap emails, then yes.

But if you’re sending emails that people love with a sound value proposition, then they will lead into a first meeting within the first 1–2. Meanwhile, the people who hate your emails will probably opt-out after 1–2 emails. So really, you have nothing to lose, and everything to gain.

Here’s a quick tip: make sure your emails aren’t all saying the same thing. They aren’t essentially saying, “Hey, did you get my last email?”

You should use your extra emails to systematically sound out different value propositions, for example, the pain vs. gain, to see what resonates with your prospective clients.

Here’s a system you can follow to scale your outbound emails.

1. Know your customer

This is what we call a sales-driven ideal customer profile (ICP). Your marketing team has one. Your product team has one. Most businesses have at least three.

Here is an example ICP:

example ICP

How do you do this?

  1. Get inside their head. Don’t guess, ask questions! If you can’t actually go out and speak to your customers, then go the extra mile and read their LinkedIn profile. Scroll right down to the end to look at their recommendations and see which companies they follow. It will give you great insight into what they like and value. By making an effort to understand the language they use and the type of people that they connect with, you will get a much more informed idea of how to write an email that speaks directly to them.
  2. Get to know their digital playground. Where do they go to hang out online and who are they chatting with? This goes beyond looking at LinkedIn. Check out their activity on Twitter or Facebook. Is there a particular meme that they’re sharing around with their friends and colleagues that you can potentially use to break the ice?
  3. Think about the rational challenges they face. This doesn’t just mean the challenge they face that you are already planning to solve. It relates to daily challenges in their business or day-to-day life. Why should I care, I hear you ask. Well, again, it’s going to give you that all-around picture. As I’ve mentioned in previous posts, in today’s customer-centric buying cycle, people are inclined to make emotional decisions first and then rationalise them with data. You need to truly understand your customer to tap into their emotions when you’re writing your emails.

2. Build your IMPACT matrix

So you’ve got this idea of your ICP and you also know how you can impact their business. Now you need to zoom in on whether you can alleviate the pain of challenges they’re facing, or bring a potentially valuable change to their business.

To really simplify this, people are motivated by the opportunity to solve pain in their business or increase their revenue and market share.

But don’t just focus on the positive or the negative. That’s the trick to this, and that’s why you need an email series, rather than just one.

Through multiple emails, you can create what I like to call multi-touch engagement.

Some people respond more strongly to the focus of pain whereas others respond more strongly to the focus of gain.

Your job is to mix the two up and create multiple value propositions.

This prospecting IMPACT matrix will help:

IMPACT matrix

Across the top, list the different features of your product that could provide value to your prospects. This is never to be shared during the prospecting stage but used to identify specific areas where you could positively IMPACT their business. This is just the start to building out your checklist.

Next step is to focus on the specific PAIN you are looking to solve. It might be something such as they’re experiencing an issue with loss of productivity. You will know this from your Research (remember the three R’s?). So that’s clearly costing them in revenue by increasing the cost of goods and reducing the amount they can ship.

You can make a REFERENCE to another customer who had a similar situation or experience. It could be that you knew two manufacturers who were dealing with a loss of productivity which was having a negative impact on their business.

Fill in the first line with your Reference point.

Now think about the REWARD. In this case, it might be, “Here’s an article from the Harvard Business Review which talks about how you can improve productivity in your manufacturing environment.”

Put that into the Reward section of the table graph.

Now for each email, the Reference and Reward will change, as will the pain vs. gain focus. Get it?

Overall, your task is to get rid of their pain altogether. And if you get them to think that you can within your email series, or better yet, secure a face-to-face meeting, then you’ve got the system down pat.

3. Now it is time to compose your emails

Create a timeline for sending out all of your emails. Think along the lines of one email every 4–8 business days. It’s really important that you plan out your emails so that you spread out your key messages for maximum effect focusing on the IMPACT for their business.

A common trap that a lot of people fall into is getting so excited about telling their ICP what they can do for them, that they give it all upfront in the first email. They have nothing to say after that and start writing emails like;

“Just checking to see if you read my last email” or even worse. “I’m just reaching out about my earlier email”.

Stop these bad behaviours immediately! This is a long-haul game, and you’ve got to think of it like that.

Remember, this is not about your ability to be likeable and impressive. It’s about your ability to create a structured sequence of emails for each business relationship you’re trying to nurture.

Do you remember what the third R was? It was Request.

When you are prospecting, it is to begin a conversation. Most people ask for 15 minutes of your time. What for? People know you want to use that time to sell them something. Why not change your request to something that your customer values. A meeting with an industry expert? A chance to learn from their colleagues?

Now you have crafted your emails, it is not time to set and forget and let the sequence of emails run their course. You need to constantly refine your message.

Which brings me back to the email tracking and bulk mail-out tools I mentioned earlier. They help you measure your performance over time. Look at them along the way, not just when your email series is over.

If results show that you’ve got an early subject line right and that it’s created enough intrigue to make someone open your email, then that’s great, but not if it doesn’t follow through as results.

However, it is still useful because it can help you understand what’s resonating and what’s making people engage, and you can tweak future emails to improve your conversion metrics.

I consider an email successful when it receives a reply. Otherwise known as a response to your Request.

So always have that endgame in mind — of getting your ICP to engage with the Request or with information you sent out.


As we’ve discussed, while the volume of emails people receive has increased, it’s still a powerful way to reach people, and it can be an efficient method for engagement when used correctly.

By following the three R’s and spacing out your email series, you will set yourself up for success as well as improve your relationship building capacity.

To get the best results, integrate your email strategy with other channels of engagement to maximise your chances of connecting. Think of it as an extension of multi-touch engagement — emails shouldn’t work in isolation!

And don’t forget to use tracking tools to your advantage. The value of understanding what engages and converts your ICP cannot be underestimated.

Remember how at the start of this article, I said you cannot sell over email? That’s still true. But in the long run, it’s worth your time to master the tools, best practice and strategies for scaling outbound sales emails, so that you can use them to bring you one step closer to selling in person and securing a meeting.