Cold Emailing a CEO

Published 3 months ago • 3 min read

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DemandJen Weekly Newsletter

Making Complex Sales Simpler

Here’s what you’ll get this week (and every week):

A cold email before/after rewrite from one of YOUR submitted cold emails
A tactic to make complex sales simpler
Where you’ll find me this month
Rescue pup of the week

Cold Email Rewrite of the Week:

This week’s submission is a fun one. The sender is cold emailing the CEO of Container Store.

One of my clients got a reply from a cold email to Chuck E. Cheese’s CEO in < 24 hours after our workshop.

Let’s see if we can help this week’s sender get the same result!

Here’s what he submitted:

Let’s start with the positives.

It’s easy on the eyes. Lots of white space (no chunky paragraphs), short sentences, and no buzzwords. This reduces the effort required by the reader. Execs are skimming their emails - not reading them like fiction novels.

And, I love the use of “either way” at the close. Most cold emails sound desperate to book a meeting. “Either way” is a wonderful way to avoid a desperate, selfish tone.

Now, here’s what I worked on in the rewrite.

The upfront sentence is kind. But its placement at the top feels like we’re trying to sweeten up the reader. It makes for an awkward transition to the next sentence.

When it’s not directly tied to the subject matter of the email, I prefer to move comments like these to the PS.

BTW - this is a REALLY common pattern in the cold emails I review. We don’t have to flatter the reader. We just need to be relevant.

I prefer to make the 1st sentence about an objective/goal the CEO has shared about their business. I found this intel on Container Store’s investor relations page in their Q1 Earnings presentation (published August 2024).

Next - the problem hypothesis. I like that he included one before jumping into a solution (many don’t).

But “overspending on communications expenses” feels broad. Readers crave specificity. Every seller claims to save prospects time, money, and risk, but it’s missing specifics and social proof.

I checked the sender’s website and found some studies with other retailers. I’ll use content from those to tell that story.

Here’s my rewrite:

Want a rewrite of one of YOUR cold emails to a target account?

Reply to this newsletter with the account, the subject line, and your email.

I’ll pick one, anonymize it, and feature it in a future newsletter.

(And please consider forwarding this offer to others on your team.)

Tactic of the Week:

By end of year, 40-60% of the opportunities in your forecast will be lost to “no decision”.

It’s a bigger competitor than any competitor in your space.

How can we pre-empt a “no decision” outcome?

First, we need to build a point of view on the cost of inaction (COI).

Here’s an easy, free first step you can take today to build one.

Where You’ll Find Me:

I’m in London this week to run a pipeline generation workshop for an all-star team of 100 sellers, marketers, CS, and product leaders.

Next week, I’m headed to Vegas to speak at 6sense’s Breakthrough event. This is my first keynote speaking on a Vegas mainstage. I'm super excited and grateful for this opportunity! Wish me luck!