The Evolution of Cold Email

Prospecting has always been one of my favorite sales activities. Most people are surprised to hear this when I tell them because prospecting is generally looked at as one of the most challenging parts of the job. Indeed, most salespeople begin their career in a full-time prospecting role and they are overjoyed to get promoted as they do not need to think about what they consider to be a chore nearly as much as they used to.

What makes prospecting particularly challenging in my opinion comes down to two different problems: it is tedious and full of rejection. Prospecting requires a lot of time spent identifying good targets within your Ideal Customer Profile (ICP) and drafting correspondence that is likely to yield a response. The behaviors of writing emails and cold calling people over and over again can become repetitive. And the reality is that the overwhelming majority of the time, you will be met with no response or a rejection.

This is why I often ask Sales Development Representative (SDR) candidates if they like to win or hate to lose more. While I believe that more mature sales reps should hate to lose, the opposite is true in the SDR role: you need to love to win. The reason for that is because winning will be quite rare. So you better really love and appreciate the wins to keep yourself motivated. If you hate losing, then you will probably not last very long, because the losses pile up quickly.

A few years ago, I wrote a book “Authentic Selling: How to Use the Principles of Sales in Everyday Life” which accurately predicted current trends around Artificial Intelligence (AI) in the sales world. I had incorporated a chapter in the book entirely dedicated to the art of cold e-mailing. Why do I love it so much? Well, I was an English major in college with a certificate in Creative Writing, so I guess you could say that a lot of the job not only comes naturally to me, but also is something I’ve always enjoyed doing. I guess I have a knack for being able to read peoples’ personalities and I enjoy being able to make a legitimate connection with them.

Since I started my sales career, I have deployed a methodology that has worked time and time again. I remember in the early days of Next Caller, which was a Y-Combinator company, I heard empirically from the co-Founders that even Sam Altman was telling them he had never seen a sales rep get the type of results I was getting, booking meetings left and right with decision-makers across the Fortune 100. I’ve been quite open about what this methodology is as I have been invited to speak at various events or do podcasts and I even built an online course about it. Suffice it to say, I’m discouraged to see the talking heads in the industry continuing to pump up the same concepts to great fanfare knowing full well that they are not bringing anything truly innovative to the table.

Here is a shocking statement: the days of personalization are dead. In a world where AI is ubiquitous in the modern tech stack, it is very easy for lots of companies to pump out messages en masse to their audience that feel to the recipient like they were actually personalized for them. There are even video tools out there that can make it seem like someone recorded a video for you when the reality is they filmed it for thousands of recipients, merely swapping out the name of the individual as it appears on some notecard in the video or something to that effect.

Here is another reality: recipients do not have any more time in their days to spare than they did five or ten years ago before all of this AI stuff was commonplace in our industry. The amount of time our buyers have is finite and unchanging. The only variable that has changed is the number of cold emails they are receiving that “feel” completely customized.

What to make of this? It’s quite simple. The bar has risen for what is now “good” outreach. Sure, we all get that junk on LinkedIn from spammers who seem to be lost in another decade, with bullet points and statistics about why their service is great. As I write this, I had to block someone who connected with me on LinkedIn a few days ago who has bombarded me with five messages this weekend alone. I’m not talking about these people – they seem lost in the past and have not even evolved to pretend that they are trying.

But most of the market is indeed trying to leverage AI and by doing so, they are making it so buyers are now wary of what might be AI and what is not. This means that it is more important than ever to go out of your way to stand out from the crowd.

The name of my online course is “Weirder Than Waldo.” In the “Where’s Waldo” books, Waldo was this odd character who was dressed kind of like a geek. He was someone who should stick out in a crowd because of how weird he was, but he was nearly impossible to find in the books. Thus the name of the course was born. It’s my opinion that you need to be weirder than Waldo if you want to really stick out from the crowd. That means you need to be doing something that everyone else is not doing. And what everyone is doing right now is using AI to write personalized emails. 

So, what is that thing? I think it’s rather obvious. I’ll give you a hint: what can you do that AI cannot do?

AI does not have a soul. AI didn’t go to college, have a favorite sports team, or mentor for the same volunteer program as your buyer. What makes you authentically human is that you have shared values and shared experiences with the people you sell to. If you are wary that your buyer might be trying to deduce what is AI and what is not, a simple way to break through the noise is to make it obvious that you are a human.

Recently, an Account Executive candidate emailed me a video message about why he wanted me to hire him. I assumed the video was going to be spam – something he had sent to dozens of companies. When I watched it, I realized it was actually made for me. He specifically mentioned how he found out about the job, why he was excited about it, and how he hoped he was not too late to the game given that it had been posted weeks before. I responded simply because I knew he took the time out of his day to go to great lengths to get my attention. And I am glad that I did, because he is an awesome candidate.

People are tribal. It is just a simple fact about our evolutionary biology that we tend to associate with people who are similar to us. We feel safer that way. Unfortunately, this has led to all sorts of horrible things in the world, like wars. I’m not suggesting it’s a good thing. I’m just suggesting it’s the reality. We have a biological self-preservationist instinct, and this is what draws us to other people who share our values. It is also why our political discussions seem so stilted these days. For many people, you are either on Team Red or Team Blue, and you are perfectly fine with being a total hypocrite if it keeps you in the good graces of other members of your team.

Whenever I research a prospect, I think through the lens of shared values. What is it about the buyer from the perspective of their values or experiences that aligns with my own? And how can I take whatever that thing is and make it relevant to what I am selling?

A good example of this would be when I reached out to a business leader at a top bank a year or two ago. She had just won an award as a top woman in banking. Now, I’m sure there are many guys like me who congratulated her on the award. AI can personalize that. But here’s the thing – she knows she won the award. You are not providing any value by reminding her something she already knows about herself. It’s no different than when I got an email from an AI bot about my book. When I challenged the bot about its favorite chapter, it got flustered. So these types of pleasantries just come across as hollow.

In my instance, my wife also works in banking, and I know from talking to her how sometimes there can be challenges being a woman in a male-dominated environment. My mother was the first woman in a non-administrative role in her law firm growing up, and she used to take me to work sometimes. And my grandmother was in the travel agency business with my grandfather, and a very strong, matriarchal figure for my entire family. All this to say, I like to think I truly understand and value powerful women as I have been surrounded by them throughout my life and they happen to be the people I care about the most in this world.

Naturally, this is what I wrote about when approaching this individual. I didn’t do it to suck up to her – I did it because I genuinely appreciated what the award meant. I told her that I figured she might be open to new ideas on account of her winning that award and introduced my product. She was enthusiastic about it and it opened up an opportunity for my prior company.

This example is one of many that I could give. Sadly, I see too many sales leaders out there who shrug their shoulders at this approach because it is “time intensive.” I don’t know about you, but sometimes part of running a successful business is a lot more than thinking about it like running a call center. The positive sentiment I have created across every brand I have worked for by putting a smile on someone’s face is priceless. Hopefully the industry will wake up and smell the roses sometime soon, for the sake of inboxes everywhere.