This is more than just a post on conversion copywriting for email. It’s your ticket to confidently take on email projects that would have previously given you pause. Made to teach you from the ground up, this resource is inclusive of everything you need to know about conversion copywriting for email. It’s so inclusive, in fact, we nearly published it as a book. So bookmark it now and refer to it to answer all your email-related questions. This is part III of IV.

So you now know how to build an email list of hot, interested leads. And you know how to get more prospects to open and click. (Right? If you don’t feel like a young Jedi master of both, check out part I (on building your list) here and part II (on clicks and opens) here. Otherwise, buckle up to see which type of email you should send to whom when.)

Automated Emails (aka How to Find Notifications of Bank Deposits Every Time You Look at Your Phone)

The first email blast was sent in 1978.

Yes, 1978. Back when computers were “computer terminals” and looked like this:

Meaning Gary Thuerk didn’t even use a PC. He used an ARPAnet terminal to send his email blast.

Batch-and-blast emails have been around for over 4 decades.

And email has gotten a lot more sophisticated since then. And with more advanced technology, comes better opportunity.

At this point, only sending campaign email blasts is akin to relying on a rotary phone for your communication or saying “Groovy” unironically.

Join us in the 21st century.

But you shouldn’t just adopt email to keep up with the times…

Automated email has huge benefits in every industry.

Because of this we’re going to do a deep dive into automated email. So you can get the most out of it.

Strap in. Read this end to end. And go get yourself some results money.

Who should send automated emails?

If you’re looking for clarity on what exactly we mean by “automated” allow me to clear it up. Automated email simply means email that is triggered by an event (usually one taken by the user), rather than being sent manually.

So if someone opt-ins to our excellent pop up from part I: Definitive Email Guide, and we’ve set up a welcome sequence in our ESP, then that sequence is triggered by their action:

So who should be sending automated emails?

Or an even better question: how can you know if you should send automated emails?

The answer is quite simple…

If you do business online, you should send automated emails.


If you have a website, you should have an opt-in on it with an automated welcome email. (So the website you poured blood, sweat and money into actually generates leads, instead of just being a forgettable cyber-billboard.)

Even if you don’t have a website, if you find clients online, you should have an automated follow-up process for new leads.

Yes, this can feel discouraging or like a lot of work. But as you can tell from the examples I just gave, your automated email sequences don’t have to be complex.

And we’re going to walk you through specific examples in this guide, so you can plug-and-play the strategy into your own business.

Even if you’re a newbie freelancer without any complex online sales process, I’m going to show you a sequence you can set up.

Let’s start with how to plan any automated email sequence.

How to plan an automated email sequence

Planning a sequence is similar to planning an email (like we did earlier).

The difference is that you have to think beyond just the transformation within a single email, but extend that to the journey the customer goes through the sequence.

Jo teaches how to plan the transformation journey using Trello, but we’re going to take a step back here. I’m going to show you how to identify which triggers you should be creating automations for first, before we get into planning each sequence.

Step 1. Identify the right triggers

First – a quick 101 on triggers versus segments.

A trigger is any condition that starts an automation.

A trigger can be:

  • An event happens (submitted form, purchase made, email opened) or doesn’t happen
  • A property (custom field) has certain value
  • User joins or leaves a segment

Segments, in return, can be based on events and properties, as well as any other condition.

Segments help us:

  • Structure the user base
  • Conveniently trigger campaigns without having to think about conditions every time.

You can trigger a campaign just fine, even if you don’t have a single segment. However, it is recommended to have them for clarity and convenience.

So when we’re planning which triggers are important for creating sequences, we can use our rule about segmentation from earlier:

It only matters if it matters.

Should you send a sequence to someone if they clicked a campaign email last week?

You could, but do you have a reason to? (Maybe, maybe not.)

What about if someone fills out a contact form on your website?

Now that’s a clear case where your subscriber is looking for a response.

Which makes it a great automation trigger.

When you’re crafting your automation strategy, you want to find all the triggers that are an important part of your subscribers’ journeys to becoming customers.

That’s why in my ecommerce email template I use “Lifecycle Stage” as an important part of planning any ecommerce email.

In ecommerce, lifecycle always matters. And you want to set up a sequence for each lifecycle segment.

The same principle is true in SaaS with pirate metrics, and lead scoring in B2B. It always matters. And you should build sequences for each significant shift in the customer journey.

To create an entire Automated Email Marketing Program, you need to identify every trigger that matters.

Then you can start planning each individual sequence.

(Now just a note for advanced email conversion copywriters. Technically you can use behavior data beyond triggers like… 

  • Skipping on individual emails within a campaign if they’re irrelevant like promoting a feature only if it hasn’t been used
  • Stopping the campaign if, for example, the user upgrades
  • Modifying each email using Liquid (adding custom fields or excluding certain copy)

So just be aware that although planning with triggers can take you far, there are other levers available to pull, should you need them.)

Step 2. Identify your Stages of Awareness

Once you know which triggers are essential for your customers, let’s plan the sequence for each trigger.

There are 2 question you need to answer:

  1. What is the beginning Stage of Awareness for your triggered segment?
  2. What is the end goal of your sequence?

The answers to those two questions show you where to start and where to end. So you move your prospects from where they are to where you need them to be.

This is what Jo used Trello to map out:

Each email brings our subscribers to the next Stage of Awareness, until we’re at the final stage we need them to be at.

Jo’s example is an onboarding sequence with an end goal of converting free trial users to paid. So the goal is a sale, and we need subscribers to be Most Aware (to get them to convert).

And because this sequence is primarily new subscribers who don’t know much about the product, her subscribers start in Pain Aware (also referred to as Problem Aware).

This is how I plan out a sequence. By using the prompts below, I make where showing the beginning and ending stage of each individual email, to get from our starting stage of awareness to our end goal:

If you’re planning a SaaS sequence, replace “Lifecycle” with “Pirate Metric”.

And if you’re planning a B2B sequence, replace “Lifecycle” with “Pipeline Stage” or “Lead Score”.

Step 3. Plan each individual email

Now that you’ve got your sequence mapped out, we just need to put the puzzle pieces into place.

Which means planning our individual emails.

With the beginning and ending SOA mapped out for each individual email:

We need to plan & craft each individual email.

Go back to “Advanced Email Copywriting: Increase Opens & Clicks” for a walkthrough of how to do this.

You’ll end up with a clear overarching journey. Plus individual emails that reflect the transformation you need to move the prospect through the Stages of Awareness. Meaning you have an end-to-end sequence built for conversions.

To see this process in action, let’s breakdown the most important sequence for ecommerce, SaaS, and B2B:

The welcome sequence.

(Or onboarding as its known the SaaS space.)

This sequence is critical because every new subscriber gets it. And it targets one of our most profitable segments: recent subscribers.

How to Turn New Leads Into Customers: Welcome Sequences for Ecommerce, SaaS, and B2B

The Ecommerce Welcome Sequence

Most ecommerce brands have a welcome sequence in place.

Unfortunately, many of them look like this:

…And that’s it.

Nothing to explain the value of the brand. Nothing to encourage people to engage or find out more. Nothing to even sell.

Just “Welcome, First Name!” and a few buttons.

We can do better. A lot better.

And make more money off every person who subscribes to our list.

And of course, this may vary greatly depending on your brand, but the welcome sequence below can be used for 95% of ecommerce brands (and adapted for the rest).

The SaaS Onboarding Sequence

While SaaS companies may have overlooked onboarding sequences in the past, industry experts like Claire Sullentrop and Val Geisler are making it clear the consequences of overlooking this email sequence.

When optimized sequences produce results like tripling paid conversions, you can’t overlook them any longer.

So while an email like this:

With its 3 separate links to totally unrelated content and wishy-washy call-to-action may have been relied on in the past, there is too much at stake to continue relying on a lukewarm onboarding email.

There is a better way forward. And it doesn’t need to be overly complex:

The B2B Welcome Sequence

With lead magnets, follow-up sequences, segmentation and many other options…

Crafting a B2B welcome sequence can feel overwhelming. There are so many moving parts, it can feel like an insurmountable task.

Thankfully, I’m about to share a simple sequence that’s been working well for me.

It’s four parts and dead easy. And it does something unlike the SaaS and ecommerce sequences:

It creates a sales opportunity. An opportunity for your new subscribers to raise their hand and say, “Yes! I’d like a sales call from you.”

Which makes it incredibly powerful.

This 4-part sequence was developed after much trial-and-error and can be used to convert even the smallest of lists:

The magic here is two-fold:

  1. Every email provides value. So those who are ready to convert, do. And those who aren’t, still get value from each email.
  2. Then, they get the survey email. And since each email has been value-packed with useful content, they’re eager to read this one too.

The survey email includes an easy link and a short survey.

Then, I reach out to those who are a good fit for my services in a non-skeezy way to follow up. (Since I can tell from their survey that they’re the right fit.)

Campaign emails that bring home the bacon

When most of us think of “email marketing”, we’re thinking about campaign emails.

It’s known by many aliases… the “newsletter email”, an “email blast” or “bulk email”. Essentially, the campaign email is the original “one-to-many” style that was the beginning of email marketing.

As email marketing has matured, the campaign email now has many different styles beyond just a classic “newsletter”.

Which can make you wonder: “Which format and strategy will work best for my brand?” But even with all of today’s fancy automations, the tried-and-true campaign email isn’t any less important.

Let’s get into the nitty gritty of how we can actually get this done.

The strategy behind the campaign email

Remember when we talked about how to grow your list?

We used the term “branded newsletter”. We explained that having a compelling, specific reason for your regular newsletters would help you gain subscribers.

And now, we’re not just going to use that strategy for new subscribers. We’re going to use that strategy to make your campaign email perform.

But even if you don’t “brand” your newsletter – meaning give it an outward-facing name and description – it should still have a “value proposition” so you stay really clear on why subscribers should care.

There are a lot of potential value props for your newsletter, which are ultimately for you to decide. But here are some common themes:

  1. Exclusive sales/discounts on your products
  2. New product/feature announcements
  3. Giveaways, events, and other community-based marketing campaigns
  4. User-generated & partnership content
  5. External links to valuable brand content
  6. Exclusive, valuable content in the email itself (or an exclusive landing page)

Now, you may be thinking… wait a second. I send discounts AND new product announcements AND links to content.

Not an issue. While it’s typical better to run with one theme, most of us have more than one thing to send to our audience.

If you’ve got an outward facing “branded newsletter” though… it’s best to keep things streamlined (and memorable for your prospect) by focussing on the one thing your email subscribers care about most.)

When it’s time to send a campaign email

When it’s time to actually sit down and write one of your brand’s campaign emails, you’re going to follow the sage advice already covered in Advanced Email Copywriting: Increase Opens & Clicks.

Which gets into the nitty gritty of how to plan, write, design and execute on creating an email that generates results.

So pick which kind of campaign email you’re going to send from our list earlier (e.g. exclusive sales vs. new product announcements), and use the guide to craft a conversion-optimized email.

And when you’re ready to transform your conversion-optimized generic email into a conversion-optimized campaign email…

You can use the following copy tricks that work particularly well with campaign emails. As always, if you want even more hands on direction to take your email marketing up a notch, check out our 10x Email Sales Program.

What’s unique about campaign email copy?

When you’re lucky enough to stand out among the dozens of other emails in a subscriber’s inbox…

And have them open up and read your campaign email…

There are two questions lingering in your reader’s subconscious as she reads your email.

1. What’s in it for me?

2. Do I want to stay subscribed to this list?

(And open the next email you send?)

“What’s in it for me?” is a classic objection that all copy should address. And “do I want to stay subscribed?” is the objection that makes the campaign email unique.

Every campaign email should address both.

Thankfully, there’s a cut-and-dry way to overcome each of these.

#1. What’s in it for me?

It’s become a marketing cliche, but the solution to this objection is one word: value.

What’s in it for the reader of your campaign email is the value you provide her.

Every campaign email you send should contain value… BUT we don’t need to use a narrow definition for that word.

Value can be something more tangible like a product discount or a giveaway.

But it can also be educational content.

Or even just an email with a relatable story.

If I close your email feeling like I took away something, then you provided me with value.

#2. Do I want to stay subscribed to this list? (And open the next email you send?)

This is where we bring the exclusivity.

All that value we just provided… if we can make it value that’s exclusive to only people subscribed to our list, then we’ve got a strong 1-2 punch for why people should stay subscribed, and continue to open and read our emails.

That means providing them offers, discounts and value you don’t also provide elsewhere.


(And if you got that Spinal Tap reference, let’s grab a beer the next time we’re at the same conference.)

Once you’ve nailed those fundamentals – which will take you all the way to 10 – then you’re ready to use the advanced tactics in this section, and get to 11.

*BUT* don’t worry about dialing your amp up to 11, until you’ve got it at 10.

Advanced Tactic #1: Segmentation

Ask any top brand who’s raking in the dough from email marketing, and they’ll tell you segmentation is fundamental.

The reason I’m including it as an “advanced” tactic is because it only becomes relevant once your list hits a few thousand.

But once you hit that range, it’s a tactic you should consider with every email campaign you send.

A good rule of thumb to remember here is to apply one goal to each segment:

Such as, you want your trials to activate. Or you want your free users to convert to paid. 

Whatever it is, apply just one big conversion goal per segment.

Then, simplify your campaign and drive that next action, hard. Once achieved, ruthlessly exit the campaign and focus your efforts on the next big goal (for another segment).

There are endless things to offer your reader, but only double down on those that take you to that single conversion goal.

And if you want to master segmentation, look back at Advanced Email Copywriting: Increase Opens & Clicks.

Remember the key takeaway was: It only matters if it matters.

Here are some examples where it will probably matter:

Advanced Tactic #2: Frequency

Again, this tactic is advanced because it requires a bit of testing…

Which means you need a few thousand people on your list before you can start dialing this in.

To optimize your campaign email frequency, you should split test, looking at the key metrics of open rates and unsubscribe rates. (We’ll dive deeper into this in section IV, set to be released Feb. 17.)

But let’s talk about best practices…

You want to email your list at least… at the very, very least… once a month. Any less frequently and your open rates and deliverability rates will go down. Your subscribers will forget who you are and your From Name will dissolve from their busy minds.

On the flip side, depending on your industry, you don’t want to email subscribers more than 3 times a week to once a day. But this is where things are more variable.

When in doubt, #swipefile

Subscribe to your competitors and top names your industry to see how others are doing it.

Take the upper limit of the typical range as your upper limit for now. (You can always test a greater frequency later.)

Professional Emails that Have the Power to Get You Anything you Want

What about those emails that you’re not sending to thousands of people?

Yeah, I’m talking about those emails you write every day. To your clients, your coworkers, and your boss…

Should we talk about those?

Yes. Yes, we should.

Like it or not, work happens over email.

And as of 2022, most of us work with people who we will never meet face-to-face.

If you’re self-employed like me, you work with clients remotely, meet your colleagues through social media and hire people who you will never meet IRL.

And no matter how many Zoom calls you schedule with these people, a big part of your relationship is going to be through email.

And even if everyone you work with sits in the same building as you… there will still be times when you’ll need to send an email that’s worded just the right way.

If you’ve ever sent a proposal and gotten back crickets, or gotten into a misunderstanding with a coworker, this section is for you.

Keep It Light

When writing any professional email, writing conversationally and with the right tone is crucial.

Sounding formal or irritated in your email isn’t going to build rapport with the person you’re writing to.

Of course, if you’re not a writer, writing conversationally can seem like an impossible task. But there are ways to make it easier on yourself.

Read your email out loud. If your emails always feature “in regards to”, “please see attached”, and “as per our previous exchange”, you’re coming across as too formal.

And this kind of formal language can cause people to tune out and miss important pieces of information that you’re giving them.

If you’ve ever had someone respond to your email with a question, but the answer to their question was ALREADY IN THE EMAIL THAT YOU SENT THEM (it’s frustrating, I know), then this might be your problem.

The simple solution is to read your email out loud. If it feels unnatural to say it, then you shouldn’t write it. And if you’re struggling to re-write it, simply say what you want to get across out loud. Then write that down.

Voila. Conversational tone transcribed.

Put it in a drawer and come back to it later. I do this every time I’m sending an important email.

When you take a break from writing your email, and stand up to go get lunch, talk to your work wife, or otherwise distract yourself mentally, you’ll come back to your email with fresh eyes.

Tools That Can Help

Thankfully, email tech is only getting more advanced.

And there are tools that can help you send the perfect email.

Hemingway app — if you don’t have “writing” as one of the special skills on your resume, the Hemingway app is a great way to avoid run-on sentences and ensure you’re communicating clearly and concisely.

Boomerang — Boomerang’s Respondable feature will rank your email on multiple factors to tell you how likely the recipient is to respond.

Grammarly — this one may be obvious, but if you’re not using Grammarly already… start. You won’t know how you wrote without it. (It’s especially useful with since launching a feature that tells you how friendly and confident the tone of your email is.)

How to Get a Response

Once you have a friendly tone to your email that clearly and casually conveys what you want to write, you need to tackle your final sentence.

That one sentence is the biggest decider of how and when your recipient will respond to you.

The kiss of death is ending with “let me know”.

The day I stopped ending my emails with “let me know” and started ending them with simple yes or no responses, my response rates from clients shot up considerably.

Less chasing people down. More of the answers you need.

And if that doesn’t work, follow up. (Which is the real finishing move.)

When In Doubt, Reach Back Out

Here’s what all salespeople since the dawn of time already know: follow-up is the key to getting what you want.

To get his dream job at Foursquare, one recent grad followed up 7 times on his initial email to get through to the CEO.

He then went on to become Foursquare’s Director of Business Development.

The key to following-up without being an annoying is this: keep it simple.

No additional explanation. No new information. They already have your original email at the beginning of the thread.

One, maybe two sentences is plenty.


“Hey, I know your inbox is crowded, so I wanted to make sure you saw this. [Re-state the original question.]”


“Hi, following up again. Is there anything I can clarify in the original email?”

And so on.

Mix it up every time. Add in a new, helpful “yes or no” question they can easily respond to. 

And use a tool like Boomerang or Spark to bring the email back to your inbox at whatever day and time you like:

Or, if you’ve got a lot of emails you need to follow-up on and you want to be efficient, you can check in on all your email follow-up at the same time each week.

I do my Weekly Review on Monday morning, but I know a lot of people prefer Fridays or Sundays. (And yes, I schedule going to the gym. Because that’s the only way it’ll ever happen.)

During my Weekly Review, I check in on my mail’s smart inbox called “Waiting For” (a phrase borrowed from David Allen’s Getting Things Done).

Whenever I send a message and I know it needs a response, I give it a green flag. And Mail automatically adds it to “Waiting For”. Then I can comb through the not-replied-to messages, and follow-up weekly. 

I’ve found weekly is a good cadence for most follow-up. Giving people the time they need to regroup and get back to me. (If something is more urgent than that, it usually makes sense to communicate more instantly through Slack or Asana.)

Those are the general rules for following-up. And no matter how perfectly you word that first email, you’ll never get a 100% response rates to that first email. Following-up is the answer.

So by now you have a conversion copywriting for email e-d-u-c-a-t-i-o-n. You know how to build your list. You know how to get your list to open and engage with you. You even know how and when to automate. And how and when to send classic campaign emails. If you think you know it all, you kind of do! (Go, you!) Except this one kinda important thing…

Read part IV of IV: Optimize Your Email Copywriting with Hard Numbers right here.