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My inbox is like a box of chocolates: You never know what you’re gonna get (with apologies to Forrest Gump).
Just today I received:
I’ll bet your inbox is like a box of chocolates too — because pretty much everyone’s is. And that includes your email subscribers.
How can you make sure your emails are ones they engage with? Let’s discuss.
Table of Contents
There are many types of marketing emails, but these are the four with the highest engagement.
There’s a moment right after someone signs up for your list where they’re still curious. Still paying attention. Still wondering if they made the right decision.
That moment? It’s the honeymoon period.
And a well-timed, well-crafted welcome email (or even better, a short welcome series) doesn’t just capitalize on that moment – it can become the highest-performing message in your entire program.
Case in point: I worked with a B2C client that sells professional training courses. Their welcome email didn’t just beat the performance of their regular sends, it crushed it.
You can get the details on the case study here.
Yes, the revenue-generated-per-thousand-emails-sent (RPME) for the welcome message was three times that of the company’s average manual send. And the conversion rate? More than five times their manual send average.
And this wasn’t some fluke or one-time promo. It was their automated welcome email. The quiet overachiever that runs in the background and never takes a day off.
So why does it work so well?
Because the welcome email hits when attention, intent, and goodwill are at their peak. Your new subscriber is expecting to hear from you. They want to know what they just signed up for. They’re open to your message … maybe more than they’ll ever be again.
A strong welcome email:
Think of it this way: If someone shows up on your metaphorical porch and rings the bell, a welcome email is you opening the door and saying, “Hey, glad you’re here. Let me show you around.”
It’s not just polite. It’s powerful.
Welcome emails aren’t optional. They’re foundational. If you’re not optimizing this part of your program, you’re leaving easy revenue and long-term relationship equity on the table.
If welcome emails are the honeymoon, triggered emails are the “You left your keys on the counter” text that brings someone back before the door fully closes.
These automated sends – things like cart abandonment and browse abandonment emails – aren’t just polite reminders. They’re workhorses. Silent performers. Always-on revenue generators.
And they work because they’re behavior-based. You’re not guessing what the subscriber might be interested in — you know. They told you with their actions.
Take abandoned cart emails. I worked with a DTC ecommerce brand where the abandonment message was outperforming the client’s regular promotional emails by a wide margin. Open rates were 50%+ above average. Click-throughs? More than double. Conversion rate? More than 2.0%. Revenue-per-email-sent? Through the roof (like “$18 in revenue for every email sent” through the roof) – see below.
Why? Because timing and relevance are baked in.
These types of triggered emails, especially when they’re thoughtfully written, designed with intent, and sent promptly, routinely outperform the rest of the program.
They feel personal. They’re timely. And they’re directly tied to the recipient’s behavior, which makes them incredibly effective.
So if you’re not yet leaning into triggered sends as part of your email strategy? That’s a gap worth closing.
Want more information on this case study? You’ll find it here.
These are my favorite emails. They are the ones that show up with something delightful, informative, or just plain entertaining – and don’t immediately try to sell you something.
I call them value-first emails, and they’re a cornerstone of any long-term nurture strategy.
Instead of pushing a product, you’re offering a moment. A recipe. A puppy video. A quirky holiday tie-in that sparks curiosity or gives your reader a reason to smile.
And that’s the key: They open because they want to. Not because they’re ready to buy, but because you’ve trained them to expect something worthwhile, even when there’s no CTA to download or demo or schedule a call.
These emails are especially useful when:
I’ve used value-first emails to help clients reverse engagement slumps, reduce unsubscribes, and keep their brand welcome in the inbox for months (sometimes years) between major campaigns.
The best ones offer something of standalone value – like a fun fact, a tool, or a video – while weaving in just enough brand presence to keep you top of mind.
No hard sell. No desperation. Just a quiet reminder that we’re still here, and still useful.
Here’s a B2C example; this was for a well-known university’s MBA program:
And here’s another, for a B2B Financial Services organization:
Want to learn more? Check out this blog post.
Email is a visual medium. Even the ones that feel like plain text.
So it makes sense that how your email looks – how it’s structured, how easy it is to scan, how well the design supports the content – can have a significant impact on engagement.
And yet, too often, design decisions are made based on internal opinions or brand aesthetics alone. Not on what actually drives performance.
Here’s what I’ve learned in 20+ years of optimizing email campaigns: The emails that get the most clicks and the highest engagement overall are the ones that adhere to design best practices.
Not overdesigned. Not fancy for the sake of being fancy. Just clean, clear layouts that make it easy for the reader to absorb your message and act on it.
A few key best practices that consistently drive results:
If you’re not sure how your current designs stack up, I broke down some more real-life examples in this article. You’ll see before-and-after examples that highlight how just a few simple design tweaks can turn an underperforming email into one that delivers.
Because at the end of the day, good email design doesn’t just look good, it performs.
In this section, I’ll discuss the four types of emails with the lowest engagement rates.
Let’s clear something up.
Yes, three of the four emails in our “highest engagement” category were automated. But that doesn’t mean any automated email is automatically effective.
Automation doesn’t guarantee relevance. It just guarantees that the email will be sent.
The most successful automated emails, like welcome messages, abandoned cart reminders, and triggered follow-ups, are all responses to something the recipient did. Someone signs up for your list. Adds an item to their cart. Requests a download or fills out a form.
There’s intent. There’s context. There’s a clear next step.
But when automation is used without regard for relevance? That’s when things fall apart.
Maybe it’s a birthday message sent to someone who never gave you their birthdate. A win-back email to someone who just made a purchase last week. A “We miss you!” nudge to a subscriber who never actually engaged with your emails in the first place.
Not only do these emails not perform, they can actively damage the relationship. Best case, they’re ignored. Worst case, they drive unsubscribes or spam complaints.
The lesson here is simple: Automation is a tool. Relevance is the strategy.
If your automated email doesn’t match where the subscriber is in that moment – what they’re thinking, doing, or expecting – it won’t engage. It won’t convert. And it won’t build trust.
Automation should feel personal. Contextual. Useful.
If it doesn’t, it’s just noise.
Let’s talk about the “promote, promote, promote” approach to email.
Yes, email can (and should) drive sales. It’s a high-ROI channel. It moves the needle. I’m not here to deny that.
But if every email you send is just a coupon, discount, or “last chance!” promo … you‘re training your list to ignore you until you’re giving something away. And that’s a tough habit to break.
Email isn’t just a transactional tool. It’s a relationship channel.
Think long-term. You’re not just looking for a one-time purchase — you’re building familiarity, trust, and relevance. That means mixing in value: useful tips, insider info, even a little brand personality. The kind of content that makes your readers glad they opened your message even if they don’t click (this time).
The truth is, consistently helpful content earns attention. And attention is the gateway to action.
So yes, promote. But don’t make every email a pitch. Otherwise, the only engagement you’ll get is unsubscribes.
When someone signs up to receive email from you, it’s the start of a relationship. And deception has no place in a healthy relationship. For instance:
You might get an increase in your open and/or click-through rates the first time you do this, but it’s unlikely they’ll take the action you actually want them to take once they realize they’ve been deceived.
And it’s unlikely they’ll open future emails from you, ending the relationship.
If your email recipients are in the United States, an opt-in is not required under CAN-SPAM. Regardless, you should ALWAYS get an explicit opt-in before sending email to someone.
Here’s why.
Being a consultant based in the United States, I’ve worked with organizations whose lists are opt-in, not-opt-in, and a mix. Here are the data points to consider.
Opt-in lists just perform better. Period. Here’s a client case study, one of a few that I’ve done over the years, that proves it.
Yes, both lists got the exact same email. Yes, we sent the emails at the same time.
The only difference was how the email addresses were acquired. The subscribers on the opt-in list had explicitly asked to receive email from this not-for-profit. The email addresses on the not-opt-in lists had been acquired without the knowledge of those on the list.
Read the full case study.
If the person receiving your email doesn’t know how you got their email address, you’re putting yourself at an increased risk of spam complaints and deliverability issues.
The non-profit featured in the case study above was cut off by their email service provider. They were no longer allowed to send, because the spam complaints they were receiving on their sends were too high. They were so high that the IP they were on, which they shared with some of the ESP’s other clients, was at risk of being blocklisted.
How high is too high? Here are the thresholds as defined by Google’s Email Sender Guidelines:
Years ago I consulted for a publisher. Their entire list was not-opt-in; in addition to scraping names off of the internet (which is an aggravated violation under the U.S. CAN-SPAM Act) they had a company-wide mandate that every employee provide them 25 new email addresses a month.
When I got there they were looking to incorporate best practices to improve performance. They were also having serious deliverability problems. There was no way I could help them with the former without fixing the latter.
They were sending from their own servers and they had their own internal deliverability team, because the reputable marketing platforms and deliverability vendors wouldn’t work with organizations whose lists were generating this level of spam complaints.
It was a bad situation. The one thing that would fix it, not overnight but eventually, was going opt-in. But that was a non-negotiable for them. They felt like the risk, and the cost of addressing the consequences of taking the risk, was worth it. I didn’t agree. I didn’t work with them much longer, but we parted amicably.
When email marketing was in its infancy, people would ask me whether they should send promotional messages or newsletters. I would say “yes,” because, like a box of chocolates, variety is also a good thing in email marketing.
The key to success is getting the right mix for your brand – and for each of your recipients.
Here are the non-negotiables:
Does that seem like a lot? Don’t be overwhelmed. Great email marketing programs aren’t built overnight. Start with one email. Then another. Then another. And before you know it you’ll be an email marketing expert.
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