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Our inboxes are cluttered with them.

Most of us hate them.

Some of we marketers, even though we know it’s cruel, hi8t the ‘spam’ button in an attempt to blacklist their email servers.

But sometimes, oh so rarely, I’m impressed by a cold sales email.

“The audacity of this email”

At every marketing conference I attend, there are inevitably sessions on these three topics:

  1. Email subject lines
  2. Knowing your customers
  3. Establishing emotional connections with your audience (usually through humor)

Well, kudos to Ian Jackson from pitchhero from managing to hit all three points, with a lasting impression I akin to Saturday Night Live’s cold opens.

This email hit my inbox at noon on a Monday… right about the point where I’m hungry, irritated with everyone and everything associated with the ‘Monday morning catch up,’ and have had enough of my inbox. Every email in my inbox at this hour is an audacity…and Ian acknowledged that.


justin topliff the audacity of this email


Email subject lines & the shift key

The composition of ‘the perfect subject line’ has long been a contested topic amongst marketers. What do we say? How should we punctuate? How can we make this more value centric? Did we get input from everyone on what they think is best? Ooooh, let’s test multiple ones for open rates!

For the love of god…Let’s be honest, we’ve over-engineered email subject lines ad nauseam. It’s. An. Email. Just like the other 200 hitting peoples’ inboxes everyday. You really want to get an open? Appeal to the pain your recipients are being subjected to every time they open their inbox. Acknowledge that you are bothering them. Flat out.

If you do that, you’ll at the very least, gain respect and avoid the ‘spam’ button. If you do it well, you’ll make me curious.

You know what else everyone hates? Putting in the effort to use the shift key.

I’m serious.

I dunno about you, but I’ve hit the point in my tech career where I’ve decided the shift key is a waste of my time (thank you, Slack)…unless I’m emailing someone I don’t know…or, in some cases, an executive. I feel like this is similar to the evolution of the telephone. Who uses a landline anymore? Who uses the shift key anymore?

Ian, either knowingly or unknowingly, used this to appeal to my subconscious. #downwithshift

Break the mold

Congrats, Ian, you got me to open a cold sales email. Now dance.

And dance he did.

How? By putting himself in my shoes & understanding my thought processes when I receive cold emails.

The formats for cold sales emails are always the same. 

  1. Short intro
  2. Business problem statement
  3. Solution offering
  4. Call to action

Ian realized that he still needed to accomplish all four of these things but that I, as a marketing executive, see hundreds of these every month.

Ian’s a smart guy because he realizes that I’m a smart guy. And he realizes that his email has almost no chance of making it through the ‘Navy SEAL bootcamp’ that’s me clearing my inbox Monday morning. For all I know, Ian is a Navy SEAL, because he brought no bullshit.

You know how many cold sales emails I see that…

  • Call out that stalking me on LinkedIn is, in fact, stalkerish? (Your Linkedin profile is impressive 😉 Stalkerish? hope not)
  • Acknowledge cold emails are always presumptuous? (isn’t cold email always presumptuous?)
  • Get to the point? (“Pitch what? Get to the point Ian!”.. Sorry….)
  • Exhibit some element of pop culture? (WINNING!)
  • Laugh at how much salespeople drink? (It’s basically a virtual sales guy (or gal) selling for you 24/7 who doesn’t expect a salary, compensation plan or have an alcohol problem)
  • Promise me a trick I haven’t seen before? (You never know, I may even wear a monocle!)
  • Understand I hate responding to these and make an effort to change my mind? (I await you deservedly annoyed response.)
  • Have a picture of Liam Neeson in them? (“If you are looking for a way to opt-out I can give you one. But if you don’t use it, I do have are a very particular set of persistent follow-up skills. Skills I have perfected over a very long sales career. Skills that make me a nightmare for non-responders. You may unsubscribe and that will be the end of it.)

None. Until Ian’s.

I almost emailed back…

…but I was so excited that I finally got a cold sales email I didn’t hate, I wanted to see what else was left in the queue! (Sorry, Ian)


justin topliff audacity round 2


See, Ian’s pretty clever here. He left the door open without letting a draft in. Low effort for me to read, low friction for his request and a low blow to his own self esteem. I like it!

I like it SO much that I didn’t respond…again…because this is turning into my favorite TV show & I can’t wait for the next episode.


justin topliff audacity round 3


Shock. GASP! Elon Musk and Mars! I can’t tell if this is American Horror Story or Rick & Morty but MMMMMMMM, I’m lovin’ it!  Sorry, James, your season finale has not yet come. Give me another episode.


justin topliff audacity 4


I never thought being told I’m elusive would be flattering but as a marketer being bombarded by salespeople, I take this as a compliment. Clearly I’m James Bond. Build me up, Ian.

Then tell me again how you know you’re bugging me, give me an easy calendaring option, then give me an out. Done, done and done.

My god, this is refreshing. So refreshing that I didn’t just finally respond to Ian, I wrote a blog post about it.

Treat people like people, not leads

I feel for SDRs, I really do. Their lives are made robotic through scripts and full of rejection. Almost everybody hates them and the work they do, except for the quota-carrying sales reps they’re enslaved by.

I was in Boston last week visiting one of our VC firms, OpenView Venture Partners. They brought marketing leaders together and I got to hear from Dave Gerhardt of Drift. Many of you may be familiar with Drift, Dave, David Cancel, or the results they’ve seen from killing lead forms and un-gating their content.

Dave’s assertion is that modern marketing has lost its way. We need to step away from SEO, automation, pipeline, etc. and get back to basics…the basics of human connection.

Nobody reacts to canned emails or marketing campaigns that came out of a cookbook anymore. We as marketers don’t like it (or fall for it), so why the hell do we keep doing it?! It’s impossible to differentiate ourselves this way anymore.

You know what’s so vogue right now? Getting off the marketing treadmill and breaking the mold. Going off script. Having conversations with people. And treating people like people, not leads.

So, kudos to you, Ian. For bringing the humanity back to cold emails.

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