Cold Email Automation & Selling in 2026
Are You Using Sales Automation?
When I talk about Sales Automation, many salespeople will have different ideas regarding what exactly is getting automated.
Is it closing a sale automatically from initial contact to receiving payment and product/service fulfillment? Or is it the automation of various individual parts of the sales process.
In the Age of Artificial Intelligence, every task humans have performed for decades and even hundreds of years is being automated. Is it good? I believe it depends.
As a salesperson who has used the telephone to make cold calls and warm calls going back to the eighties, I have always had to deal with various obstacles. I have dealt with everything from call display and hiding my number to avoiding assistants screening callers and pretending I was someone else to get through.
B2B Sales and Cold Calling
TeleSales-Pro.com was initially created as a place where I could post helpful tips and techniques for anyone cold calling prospects over the telephone.
This website/blog was a reaction to watching new salespeople in my day job struggle with selling our product and services over the phone. The fact rejection was inevitable with cold calling cleared out salespeople without the grit necessary to keep pushing forward!
After joining a start-up advertising sales company in 2015 and realizing the rate of executives answering the phone was plummeting like a rock thrown into a pond, I decided to investigate email, specifically cold-email.
Cold calling using the telephone always had challenges as you can’t pitch someone if they don’t pick up. So, is using the telephone to make cold calls a waste of time? Are there still businesses doing it?
I would suggest the phone is not a cold opportunity any longer. I don’t answer calls from unknowns, and even though it defies logic, yes, there are still businesses doing it. It won’t last in my opinion…
If you operate a business that has many salespeople making cold calls using the telephone, you may have been managing to still make sales and if your salespeople are collectively making more than a thousand calls a day, you may get through to enough prospects to keep your business viable.
The fact is, business people do not answer unknown calls to their office phones like they once did. Unless the call was previously scheduled or was from a known person, chances are your call will not get answered.
I don’t believe it’s feasible if you only have a few salespeople. If you have a small sales team there’s no way to scale your business if you are only doing cold outreach using the phone.
It’s time you looked at incorporating other methods.
When Steve Jobs launched the first iPhone on June 29, 2007 everything changed, and with the mass adoption of SMS, A whole new way of getting to busy executives expanded. As a result, it was getting progressively worse for people cold calling using the telephone as their go to method.
Even though it was proved years before the launch of the iPhone, the ability to receive emails on a mobile device enabled companies to reach their executives any time of the day or night, weekday or weekend. The Blackberry – often called the crackberry, made B2B communication via email mobile. It changed the game.
Communicating via email became ubiquitous, efficient and quite effective.
When Cold Calling Stopped Scaling
After moving on to become the Chief Marketing Officer at a media sales startup, I realized, considering my 15 years of cold calling experience going back to 2001, it was becoming extremely difficult getting decision-makers on the phone.
At that time I was still very busy selling, the telephone however, got relegated to a warmer position in my workflow. In one way or another, I have been using the telephone to make cold calls for over 25 years!
The drastic decline in prospects answering their phones had become excruciatingly painful in 2015 and back then it became obvious I should look at other ways to reach out to cold prospects. So, I started my quest to find a solution! That solution could include cold email automation, some type of email sequencing platform.
As I have been writing code, developing websites, and marketing online since the eighties, I follow tech trends. I am constantly on the lookout for emerging software tools to make my business activities easier and more effective, and this was true then.
I wanted some form of email solution so I looked at the typical list-building email clients Internet Marketers have been using for many many years to send out newsletters. The problem with email service providers like AWeber, ConvertKit, or any of the hundred others is they require a prospect to opt-in to a mailing list. This was not going to work for cold outreach.
I had a set of criteria and I went about trying to find a product that satisfied as many of my requirements as possible. I needed the ability to send a sequence of emails to potential buyers, just like a typical email client with one exception – I could enrol a prospect into my sequence without getting them to opt-in to an email list. In 2015, this was a huge challenge.
If my number one requirement was the tool not require a prospect to opt-in, it also had to be easy for any salesperson to learn and start using quickly. This posed a whole other set of problems, it had to be simple enough for anyone to easily use.
As luck would have it, there were a few tools available and I took a look under the hood of many of them before settling on a platform.
Back then all of the available cold email tools were delivered as Software As A Service (SAAS). This is not the case anymore…
Artificial Intelligence and LLMs have changed automation in ways unimaginable in 2015. And it’s not only sales, everything is being automated.
The SAAS offerings in this space are extensive. There are a hundred or more cold emailing solutions.
However, these incredible new tools were built-by and targeted-to tech startups and are built with that user in mind in my opinion and mainly it’s someone who is not an experienced salesperson. And in 2026, this is still an issue.
Sales Automation Does Not Replace Selling
As a seasoned sales practitioner, I have seen many tutorials and how-to videos on YouTube and elsewhere over the years as well as Expensive Sales Training websites, courses and tutorials. In 2015 I just needed the ability to send a sequence of pitches to prospects at scale. And I still believe this is actually where Cold Email Outreach is incredibly effective.
Even though Cold Email Outreach is no longer a tactic ONLY being used by early adopters like me, and I get cold email all the time to my various business email addresses, it’s obvious to me, many people need help getting this right which is why I am posting now.
I intend to use this website to teach and help salespeople use these tools to their maximum effect.
As we move through 2026 and beyond, I will explore the solutions to help you excel as sales professionals using cold email outreach. I will post about them here. I will let you know what’s now available and how those solutions can help you make more deals. But at the core of my intent is to help you understand selling and how to sell effectively.
Jim