How to Write Hard-Hitting Cold Email Sales Cadences That Actually Convert

 

Giving reps an email template is a surefire way to give them a bad case of templatitis. This is the disease of thinking it’s the template that makes emails work instead of the context or meta-framework, and it’s everywhere!

I can share the exact sequences, cadences, plays, and flows that I write, but it’s less powerful than zooming out to 36,000 feet and analyzing the why.

So, today we’re fighting against templatitis, and we’re diving deep into the choices I make when creating email sequences and cadences so you can create your own hard-hitting emails.

Learn From The Emails You Receive

Breaking down the syntax of emails you receive is a great way to understand why they did or didn’t work. It can also be fun to forward some of the emails you receive to the SDR team to break down as well.

I’ve seen some great teardowns from Josh Braun that back up his prospecting theories, like this one.

 

To get really good at writing cold email, I recommend researching Josh Braun, Becc Holland, and Scott Britton. Soak their lessons in, and combine your favorite techniques from each to create your own special sauce.

Follow the Data

Most sequences are too soft or too hard-hitting, and it can be tough to determine which it is and how to fix it. The solution — like with many things in sales — is to AB test anything and everything.

All facets of linguistics are pendulums to test. Even the advice I just gave can be proven out with the data — open rates, reply rates, conversion rates into meetings, all the way down the funnel to close.

We now have technologies like Outreach.io that allow you to test almost any hypothesis and easily see what kinds of emails work and which don’t.

There are three categories of things to test with your emails — mechanics, personalization, and timing.

Mechanics

• Personas (how many, which)
• Subject lines (length/tone)
• First lines
• Calls to action (CTAs)

Personalization

• Technographics
• Firmographics
• Psychographics
• Level of personalization: Level I, II, III, or hyper (I’ll talk about this more later)

Timing

• Time of day
• Length of email
• Frequency of touches

Let the data speak for itself, and listen to what it tells you. Data is the key to building the perfect email sequence and cadence, but too many people don’t like putting in the work.

The Architecture of a Sequence

Now let’s get into the architecture of your sequences.

Imagine you send 12 emails over 30 days in clusters of three. The first is a standalone email with a subject line, the next two bump the first email after a day.

Take a look at this structure. This is my signature architecture, and it’s a bit wild transposed over a million emails. This stuff is like geometry or splatter paint drawings…. LOL

Each cluster contains its own narrative.

CLUSTER I

CLUSTER II

CLUSTER III

CLUSTER IV

Justin Michael SPEARS™

Because the emails are landing more frequently, this is an assertive (formerly aggressive) style, but it does one powerful thing — it gets you to NO, Remove, Refer, or even Yes! (lol) far faster.

Name Your Strategies

I find it very useful to give different designs of clusters nicknames. Now I know that Aaron Ross used some of this lingo in Predictable Revenue to differentiate outbound prospecting (Spears) from marketing, which is casting a wider net and focusing more on an inbound approach. I took his terminology and tweaked it a bit.

RELATED: The Prospecting Problem: Balancing Inbound and Outbound Sales Strategies

What he calls a spear, I sometimes call a Compacted, or short-form, message that doesn’t look like marketing — not a ton of bullet points, no beautiful grammar.

In the above array, each cluster can have a different theme, or tell a different story. You can even think of it as a storytelling narrative arc.

At LinkedIn, my manager, Alex Wolin (now at Slack!), taught me to leverage a left brain/right brain approach. What this means to me is leveraging qualitative and quantitative factors.

So, that could look like this:

Cluster 1:

Case studies

Cluster 2:

Multimedia/visuals

Cluster 3:

Stories

Cluster 4:

Client Testimonials / ROI

Giving names to your different clusters makes it much easier to find the exact messaging you need for every occasion.

Disrupt Their Expectations

I’m a massive fan of mashups as pattern interrupts, so it’s also totally useful to mix, mash, and connect these different types of clusters.

Messy is not actually bad.

You don’t want the recipient’s brains to predict what’s coming next. So, moving from appealing to the left brain to the right, even in a single sequence, can disrupt the normal marketing they have to read.

There’s another huge differentiator here, which is how often my cadences arrive. If you space out the days like 1, 3, 5, 8, 13, prospects start to believe they’ve been falsely opted into marketing emails and will opt out!

Travis Henry and Lars of Sales Source have released a touch pattern infographic to finally answer the question of what is the optimal, most hard-hitting, touch pattern outbound cadence possible.

The Prospect Pyramid

It’s important to know that you need to reduce your contact frequency at the C-Level and raise it toward the operational or user level. This is the revelation that Steve W. Martin, Professor of Marshall School of Business at USC discovered.

This insight creates a prospect pyramid of sorts. Tony J. Hughes shares his version of this in his book, COMBO Prospecting.

 

You can check it out for free here: 4 Must-Have Touch Patterns For New Account-Based Sales Development Teams.

Cold Email Ten Commandments

Over the years, I’ve built out a variety of rules to take general templates for outbound prospecting automation sequences and make them better instantly.

1. Remove bulky signatures. That means no images or links

2. Remove all links and attachments from your first email.

3. Make sure every touch can represent all the emails. This applies to every touch in the sequences that’s a main thread (not a bump). It needs to be able to be understood holistically on its own. I borrowed this from fractals and holography.

Why?

Executives have short attention spans, and once they finally click on that 7th touch, you’ve gotta hook them, pique them, and sell them.

4. Use visuals like Venn Diagrams and wow-factor, explainer GIFs (CloudApp is a great app for this) — one image is worth 60,000 words to the human brain according to neuroscience

5. Analyze your replies. You can leverage auto-responder automation to pause the sequence until they’re back in office, or even automate placing prospects into specific auto-responders or touch patterns.

6. High open-rates are a reason to call. I call this rule, “Call on Ruleset 3.” Create an alert to notify you if a prospect has opened an email more than three times.

Assume three is one view, four is two views, five is a referral, and over six… you’re getting circulated around the water cooler. One call is worth 240 emails, so you see the power of adding visuals and phone calls to scale your outbound.

7. Brevity is the soul of wit! This is the Shakespeare rule. Make everything painfully short. Subject lines should be 1-3 words. And the body should be just three sentences with a call to action. Think mobile responsive design.

8. Build linguistic pattern interrupts — everyone — literally everyone, starts every email with “Just reaching out” or “I hope you’re doing well!” DON’T do that.

9. Slow down to speed up. You’ve got to warm up your email to avoid getting on Gmail’s bad side. So send 25, 40, 75, all the way to 150.

If you need to send more per day, feather your emails across several different addresses. Get jane.doe@acme.com and jdoe@acme.com. Keep in mind that sideloading .biz and .org is gone. It gets a demerit with spam gauges now.

10. Personalization is a game-changer on the 80/20 rule. It’s a power law, so personalize at least 20%.

Hyper-personalization is very powerful. This is the type of radically customized outreach that only a human can do. Include some bizarre tiny detail like how I uncovered that I once had a colleague who dated the best man in the CRO’s wedding. Uncovering this got me the appointment in the Boardroom a week later because he wanted to see how Sales Navigator could surface that. (Full disclosure, I used to sell Sales Navigator!)

Don’t Be Passive

So why did I title this article hard-hitting?

Because passive approaches fail — if you’re conservative, look like marketing, and have perfect syntax, you’re not going to stand out. The same goes for visual prospecting.

Diagrams that look homespun or rep-built perform way better than some slick photoshop design.

You need to be highly concise, highly assumptive, and punchy to stand out. It’s the purple cow content that truly breaks through.

It’s critical to start with the why, develop a business case that’s relevant, and leverage visual prospecting in sequences after the first email.