The "Breaking Up With You" Email
A short history of what was once a great sales email.
If you’ve been in the business of buying just about anything over the past 25-years or so, you’ve probably received “The Break Up” email from some junior sales person that is trying to pull on your heart strings to call them back or at least have you email them to tell them to pound sand.
Maybe you’ve engaged with the sales rep a bit and they think that you have a relationship there. Maybe not.
The email always looks something like this:
Dear John,
I’ve tried to reach out to a bunch of times to follow up on my offer to let you buy some PRODUCT.
I’ve not heard form you, so I suspect that this is the end of our relationship. I don’t want to bother you and I don’t want to spend my time trying to get someone to talk to me that doesn’t want to.
I guess this is the end…
Or something like that. Usually, slightly more professional, but sometimes not. I’ve seen many business owners, including
mention these as a terrible way to get his attention and I know that when I see these, I get a certain sense of relief.“Great, I don’t need to hear from you any longer!”
With that said, I can’t help feel a little bit guilty for propagating this into the sales zeitgeist.
u/brk1 on r/sales asked about the history of this email, so let me take a break from my warm milk and stories and spin you a yarn young person.
When I was at WebEx, we would use this tactic and it would work. Not only would it work, it would work beautifully. We’d get the reaction that we wanted - either, “sorry I’m busy, but this is important” or “sorry, this isn’t important to me any more”. It was great.
This was a playbook from early software sales training, when this type of thing would get a reaction (and maybe other products too, who knows, email was still new then). I had heard versions of this from Sandler, Mike Bosworth, and Skip Miller (RIP) all around the time that Y2K was becoming an issue.
Like a lot of things then, it was new and like always, people don't want to be broken up with. So we’d get a reaction to this break email, probably 7 out of 10-times. Maybe more.
Back then, we didn't have a dozen different tools that just let us spam wildly.
As a result, all emails were actually more personalized then. All of the touches were personalized, because they had to be. And there were only about 50-SaaS companies with a decent sized sales team at the time and only about 5 of them went through that training, so you didn't get the deluge of emails that you get today.
This tactic was successful at early SaaS companies and quite a few of those companies actually made it through the winter of 2001 - 2003, but during that time, they also had to fire a bunch of people. All those people that lost their jobs in that downturn started to get new jobs and just replicated their playbook because it worked previously.
When I joined both Starfish (2001) and Yahoo! Enterprise (2003), they wanted me to basically recreate the WebEx playbook line by line.
There were a bunch of us out in the world now doing the same thing that was successful for us in the past. Venture money was deep and the number of companies using this playbook grew exponentially over a few years.
The companies that were successful in that era, grew using a lot of that same playbook from 2000. Then 2008 happened. Well, quite a few people got fired in 2008 - 2009, so when they were rehired, they kept on doing what worked for them before.
Now there were 100’s of companies that hired people that had learned what works and what doesn’t. Not only that, there were 1000’s of VP’s in that time frame that received that email and said “wow, this is clever, we should use this” and they did.
From 2000 - 2010, there were a lot of sales people that used the ‘Break Up’ email and it got results.
But we didn’t have metrics on things like email sends in 2000 and we didn’t see how the success of the break up email was declining. We just knew what worked and ran with it.
Now, 25-years later, we have a million email marketing tools, there is no personalization, and there are 1000's of companies running the same play books because they worked for me at WebEx 25-years ago.
Is WebEx entirely to blame for this? There were probably other companies in that era that were doing the same thing, but during my time there, we had about 100-sales people running this play. 25-of them reported to me and it worked. WebEx was enormously successful and this was part of the playbook. It was a Hail Mary pass.
According to ESPN, a Hail Mary pass works 1 in 12 times. "I'm breaking up with you" is the junior SaaS sales rep equivalent of a Hail Mary and I'd bet that the odds that this works is still like 1 in 20.
PS - and as a total aside - some of us WebEx’ers actually cobbled together a mass email tool out of Excel and an early version of Outlook in 2000, but it was fraught with problems and only would let you send to 50-people at once. There was no way to find emails, so we had to guess at them first.last@, first_last@, flast@ etc. They were all considered a single send, so our 50-people were closer to 10. It was brutal, but it worked.