The Ultimate Guide to Email Marketing

Everything you need to know to increase email engagement rates and start conversations now


About This Guide

Over the past decade, several so-called “experts” in the world of sales and marketing have made the same, bold declaration:

“Email is dead.”

While there’s no denying that more modern communication channels, like chat, have been growing in popularity, that doesn’t mean email is going anywhere. Case in point: If you’re reading this guide, we’re betting you checked (or will check) your email at least once today. And with more than 280 billion consumer and business emails being sent every single day (a figure that’s expected to grow to 333 billion by 2022), it’s clear that businesses still see the value in using email to reach out to potential customers.

The only problem with email is that—from a customer experience perspective—it’s, well… awful. Think about all the impersonal ads, promotions, and sales pitches that are flooding your own email inbox, and how annoying it is when you have multiple people from the same company emailing you at the same time about different things. The icing on the cake, of course, is when you try to unsubscribe but keep receiving unwanted emails anyway.

☝That’s a terrible experience. But the underlying issue isn’t that email, as a channel, is dead (or dying). The issue is that as marketers and salespeople, we’ve been doing email all wrong. And that’s exactly why we wrote this guide: to offer an alternative to the traditional approach and to reimagine email as a channel that drives actual conversations.

In this guide, you’ll uncover a blueprint for building a modern, conversational email strategy—one that prioritizes creating an incredible customer experience.


Anyone who sends email on a regular basis can benefit from reading this guide. Whether you’re responsible for sending out email newsletters, or setting up lead nurturing campaigns, or managing your product’s onboarding flow, the lessons and best practices you’ll learn inside can be applied across the board.

For marketers and salespeople who are new to the world of email marketing and marketing automation, think of this guide as a recipe book you can follow for building your email strategy from scratch. It covers everything from identifying who you should target with your emails, to crafting the perfect copy, to sending your emails at the right times.

For email veterans, this guide will introduce you to a new set of tactics you can use for taking your email strategy to the next level (including how you can use an AI assistant to intelligently manage email replies and update your database with the most up to date contact information available to you today).


By the time you’ve finished reading this guide, you’ll understand, step-by-step, how to implement a conversational email strategy for your business. Unlike the old-school, “spray and pray” approach to email, conversational email emphasizes quality over quantity. Instead of playing a numbers game and hoping you’ll get a small percentage of people to open your emails, with conversational email you’re laser-focused on getting people to actually replyThe goal isn’t to get clicks, the goal is to have conversations—which is exactly what email was originally intended for.

Think about it: As a marketer or salesperson, why are you sending emails in the first place? Email marketing is about building relationships between your leads and your business. And how do you build those relationships? Through conversations. (Not clicks.)

Keep reading to learn how you can get back to email’s roots by implementing a conversational approach. You’ll also learn about different A/B tests and experiments you can run to measure and optimize your conversational email results.

Here are the 9 key topics we’ll be covering in the pages to follow:

Email Segementation

Who should you be targeting with your emails? 

One of the worst aspects of traditional email marketing is that the emails being sent are often generic, impersonal, and/or completely irrelevant. They don’t acknowledge the specific needs or pain points that different types of people have. Instead, businesses go broad, casting as wide a net as possible with their emails and treating all of their leads and customers exactly the same way. And while writing better, more personalized email copy (which you’ll learn how to do in the next section) is certainly part of the solution, there’s a crucial step that comes before that: segmentation, a.k.a. dividing your email list into smaller segments based on shared attributes.

In a study we conducted at Drift that looked at 290 cold emails, we discovered that one of the most significant factors for predicting whether or not people would reply to emails was how much segmentation companies had done before. As Drift’s VP of Strategy and Siftrock co-founder Adam Schoenfeld explained, “the killer combo is using personalization with smaller audiences. More targeted messages get more engagement.”

Of course, understanding the importance of segmentation is one thing, while figuring out how to segment your email list is another thing altogether. And the truth is, there are a lot of different ways you can do it. You can slice and dice up your email list based on all sorts of different target criteria. But when it comes to using email to start conversations, we’ve identified four key types of segmentation that stand above the rest.

  1. Segmenting by Industry: This is especially useful when you’re emailing someone for the first time. Being able to identify and refer to an industry-specific problem will go a long way in making an email (even a cold one) feel warm and relevant.
  1. Segmenting by Intent: Of course, just because someone works in an industry you sell to doesn’t mean that person is actually ready to buy. Luckily, you can also segment your email list based on signals of intent (e.g. Are leads actively researching your product or topics related to your product? Or are they visiting your pricing page over and over?). Segmenting by intent allows you to hone in on those people who are most likely to buy.
  1. Segmenting by Sales Stage: Segmenting by sales stage allows you to send emails that are tailored to the different questions and concerns leads might have as they move through your sales process. For example, you could create separate segments for new leads, leads who’ve already talked to Sales, and leads who have a proposal or contract in hand.
  1. Segmenting by Customer Lifecycle: Your email campaigns shouldn’t disappear for leads who convert into customers. After all, there will always be upsell and cross-sell opportunities on the horizon, and you’ll want to keep customers in the loop when it comes to new product releases. That being said, if someone just became a customer last week, you don’t want to start selling them right away. But sixth months later? That’s a different story. By segmenting by customer lifecycle, you can make sure you’re sending the right message at the right time.

Writing Compelling Email Copy

How do you write emails that lead to conversations?

Once you’ve successfully divided your email list into meaningful segments, you’ll be ready to write personalized email copy that addresses the specific interests and pain points of those segments. And while the concept of email personalization is nothing new, it’s often misunderstood.

For some email marketers, personalization simply means having a person’s name auto-populate at the beginning of an email based on what’s stored in your contacts database or CRM (e.g. “Hey [First Name]!”) and then having the body of the email contain some industry-specific jargon and buzzwords. Over the past decade, this has become the accepted standard. And because it’s a formula that’s so widely used, its effectiveness is waning. For potential customers, that old-school approach to personalization no longer feels very personal.

The solution? Think of email personalization as a combination of context and tone.

Your goal shouldn’t be to trick someone into thinking you’re writing a one-to-one email when you’re clearly not. Instead, your goal should be to write emails that people find relevant and that make you come across like a helpful friend—and not a corporation.

Do you have content you can share that will help people in one of your segments improve one of their businesses processes? Or, can you inspire a bit of FOMO by talking about an industry bigwig who’s using a certain approach to drive revenue? That’s the type of context you need when writing emails designed to start conversations. You need to put in the research ahead of time and make sure your message is relevant.

But that’s only half of the equation when it comes to writing compelling email copy. The other (and, arguably, more difficult) half is tone.

For years, marketers have been using the same formal, buttoned-up tone when crafting email in an attempt to come off as authoritative and trustworthy. And hey, it makes sense, right? After all, you want to convey to potential customers that you’re a professional organization. But here’s the thing: When your emails are void of personality, they sound dull and boring, and they end up blending in with all the others. In order to get your emails to stand out in today’s fully automated world, you need to double down on being human. That’s why at Drift, we always write our emails as if we’re talking to a friend or family member. The tone is informal but respectful. It’s not about being wacky or silly or making jokes, it’s about coming across like the authentic human being that you actually are.

Plain Text Email vs. HTML Email

What should your emails look like?

For years, email marketers were obsessed with using HTML to produce highly stylized emails. They designed colorful banners and borders and inserted all sorts of graphics and buttons. But eventually, most marketers and salespeople have come to see the light and realize that customers and potential customers really don’t care what business emails look like—what they really care about is the substance of what it is you’re offering, and whether or not what you’re saying is relevant.

In our recent cold email study, which looked at 290 of the most successful emails sent by marketers, SDRs, and SDR managers, we found that 87% of those emails were entirely plain text. No fancy formatting. No bells and whistles.

Remember, the goal of email marketing, whether you’re sending a cold email or sending a weekly newsletter, should be to build and strengthen relationships through conversations. By avoiding heavily designed HTML templates and using plain text instead, your emails will feel less like business emails and more like emails coming from a trusted friend. And because of that difference, people will be more likely to reply.

At Drift, we ditched highly designed HTML email years ago and never looked back. More recently, we made the case for plain text email in our book This Won’t Scale, which features 41 plays the Drift Marketing Team uses to drive growth and thrill our customers. “Opt for Plain Text Emails” is play #36.

Here’s an excerpt:

Using plain text email instead of HTML is a surefire way to get your marketing emails to end up in a person’s digital “A pile.” But to clarify, just because you’re using a plain text format doesn’t mean you only have to use text in your emails. Emojis and photos are still fair game and worth experimenting with. After all, this approach is all about making your emails feel personal (and we’re guessing your friends and family use emojis and include the occasional photo when exchanging emails).

Below is an example of a plain text email we recently sent at Drift that got a ton of engagement. A few reasons why it worked:

  • catchy subject line
  • sent from a real person (with a picture of that person to make it even more human)
  • short and well-organized (with links to get you where you need to go)
  • includes a P.S. with a call-to-action

Email Subject Lines

How do you write subject lines that cut through the noise?

With the average person now receiving 125 business emails every day, it’s hard to get your email to stand out from the crowd. Even if you’ve done everything right up until this point—you’ve segmented your email list, you’ve written compelling copy, and you’ve ditched your HTML template for plain text—you still need to pass one final gatekeeper in order get someone to open (and reply to) your emails: the subject line.

Think of your email subject line as the headline of a news article. It’s your chance to grab someone’s attention and introduce the information that’s coming next. And while it can be tempting to make your subject lines catchy and overblown in order to attract eyeballs, a better option is to keep your subject line anchored in reality and in the actual content you’re sharing. Remember: your goal here isn’t to drive clicks, it’s to start conversations. If the content of your email doesn’t line up with what you promised in the subject line, people aren’t going to have a good experience.

The solution, of course, is simple: Avoid hyperbole. And don’t try to trick people into opening your emails. Instead, you should focus your energy on writing subject lines that are relevant to your different segments, and that can succinctly address how whatever it is you’re sharing or promoting in your email can help people solve actual problems and address industry-specific needs.

In our email study, we found that the best-performing emails tend to have subject lines that are between three and six words long. However, that’s not a hard and fast rule, as there were plenty of high-performing emails that had much longer subject lines. Ultimately, in order to figure out the types (and lengths) of subject lines that work or don’t work for your business, you’re going to need to test, and test, and test some more. You can also use free tools, like the Send Check It email subject line tester, to see how your subject lines stack up against thousands of others based on attributes like scannability, length, and sentiment.

When to Send Email

When are the best days and times for emailing leads? 

After you’ve identified the right people, and you’ve created the right email (i.e. one that has compelling copy, plain text formatting, and a strong subject line), your next step is to figure out the right time to send your email. What day of the week? What time of day? What combination of day and time will optimize your chances of getting people to open your emails and start conversations? Here’s the answer:

Tuesday at 10 a.m.

Yep, seriously. That’s according to a recent study that brought together the results of 14 smaller studies—all of which looked at when companies were sending email and finding the most engagement. The biggest takeaways: Tuesday is the best day for sending email, followed by Thursday, and then Wednesday. The best time for sending email is 10 a.m., followed by 8 p.m. to midnight, and then 2 p.m.

So, case closed then, right? Onto the next section?

Not so fast.

While findings like these are interesting, you should really only think of them as jumping off points, as opposed to rules that are set in stone. Because ultimately, in order to figure out the best times to send emails to your leads and customers, you’re going to need to test out a bunch of day and time combinations to see what yields you the best results.

For example, at Drift we discovered that the best time to send our newsletters is actually over the weekend. That’s because the content of our newsletters is geared toward helping people get ready for the week ahead. Specifically, our marketing newsletter (which goes out to 20,000+ marketing & sales professionals) helps you get caught up on the latest tools and tactics, while in The One Thing, our CEO David Cancel shares one habit or mental model that will help you grow personally and professionally. The takeaway here: Don’t just rely on industry standards when it comes to figuring out the best times to send email. Take the type of email you’re sending into account as well.

Lead Nurturing Email

How do you build nurture campaigns that aren’t annoying?

In a perfect world, all of your potential customers would land on your website, qualify themselves via real-time conversations (with humans or chatbots), and then buy from your Sales team. That’s how conversational marketing works in its purest form. It’s fast, it’s streamlined, and it connects you with people who are ready to buy NOW. But what about the people who aren’t ready to buy now? How do you keep them engaged?

That’s where lead nurturing comes into play. For years, email marketers have been enrolling leads in nurturing sequences (a.k.a. drip campaigns) in order to re-engage them and help nudge them through the sales process. It’s become a default component of every email marketing strategy. The problem, however, is that it’s become so easy to set up these automated email sequences that marketers are abusing the power. They’re sending way too many emails, and enrolling the same people in multiple sequences. It’s annoying. And chaotic. And, as Drift’s VP of Operations Will Collins explained, it’s part of an outdated approach to marketing that doesn’t match the way people prefer to buy today:

So, how do we reimagine lead nurturing for today’s real-time, on-demand world? For starters, we need to stop being so annoying. We need to send fewer emails to more targeted lists of people. And we need to have technology in place that will automatically un-enroll people from nurturing sequences based on the actions they take (e.g. they convert into a customer, or they reply with the words “Unsubscribe me!”). Another way to reduce the frustration factor: Schedule sequences so that emails never land in people’s inboxes on weekends or holidays. You can also use a smart sending tool to send emails based on timezone and the time of day leads usually open their emails.

All of these little changes will add up to a better experience for potential and existing customers. But in order to truly bring your nurturing strategy into the modern era, we suggest you do the following (assuming you haven’t already): Connect your email to chat. Instead of treating email as a separate, isolated communication channel, make it as easy as possible for leads (and customers) to move from an email to having a real-time conversation.

For example, for people who are new to your sequences, you could start by adding a simple “P.S.” to the ends of your emails that let people know that your company is available to answer questions via chat. Meanwhile, for people who have moved further down your funnel, you can have starting a real-time conversation be the primary call-to-action of your emails. Pro tip: Be sure to add your chat link at the very beginning of your emails, even if you include a “proper” CTA at the bottom with the same link. After all, there are people who might be ready to chat right right away. Don’t force them to scroll.

From a customer experience perspective, connecting email to chat gives you another opportunity to make email feel more personal. Because when a lead (or customer) comes to your website from an email, you can greet them with a personalized welcome message. In addition referencing a person by name, or referencing the company they work at, or the industry they’re in, you can use your welcome message to say something as simple as: “Hey, we saw you were just reading one of our emails. We’re glad you’re here!”

Delivering this type of streamlined, hyper-personalized experience is something we explore in-depth in our Conversational ABM guide. The guide, which we created with our friends at Demandbase, gives a step-by-step breakdown of how you can roll out the red carpet for your company’s target accounts and provide a real-time, on-demand buying experience.

Managing Email Replies

How do you create incredible experiences for the people who reply to your emails?

At Drift, we consider replies to be the most important email marketing metric. Because if an email gets replies, not only is the subject line resonating, the message of your email is resonating too. The tricky party about replies, however, is figuring out what to do after you get them. Because the reality is, after adopting a conversational approach to email marketing and optimizing for replies (not clicks), the influx of replies you get can be a lot to handle. But trust us: This is a good problem to have. It’s a sign that people are engaged and ready to keep the conversation going.

As an email marketer, it’s your responsibility to not let these people down! If they’ve taken the time to reply, you need to follow up, regardless of how many dozens (or hundreds) of replies you get. It sounds like something that isn’t easy to scale… and that’s exactly why it’s so valuable. Not every brand takes the time to personally respond to every message. Those that do are showing they care, and providing a better experience.

That being said, there are now tools available that can help you manage your email replies more efficiently and ensure that no reply from a lead or customer falls through the cracks. For example, using Drift Email, you can have email replies automatically routed to the right sales reps based on your CRM routing rules. What’s more, your sales reps can choose to receive real-time alerts anytime one of their leads sends a reply so they can jump in and answer questions at a moment’s notice. Drift Email can also update and automatically remove contacts from your CRM based on the out of office messages and other auto-replies you receive. The end result is that all of the busywork associated with managing email replies is taken care of for you, freeing you up to focus on more important things—like having one-to-one conversations.

Email Experimentation

What new email tactics have been gaining traction?

What we’ve shared so far in this guide are a core set of principles and steps you can follow for adopting a conversational approach to email marketing. But for those of you who have already laid the groundwork for a conversational email strategy and are ready to take things to the next level, we’ve got three tactics for you to try. And FYI: These are all tactics we’ve been using (and testing) here at Drift in order to speed up our sales cycle and convert more of our email replies into sales opportunities.

1. Add calendar links to email signatures.

Instead of forcing leads to endure endless email back-and-forths and/or annoying games of phone tag in order to schedule meetings with Sales or Customer Success, you can include links to reps’ calendars directly in their email signatures. That way, with a few clicks, leads and customers can view availability and schedule meetings for days/times that work best for them. Then, once a meeting is scheduled, confirmation emails get sent automatically to both parties. It’s a real-time, on-demand approach to scheduling—no waiting, no back-and-forths, no annoyingness. It’s a simple change to an often-overlooked aspect of email (re: the signature), but if you’re serious about converting your email into actual opportunities, it’s absolutely worth doing.

2. Send abandonment emails to leads who go through your scheduling flow but don’t end up scheduling meetings.

Of course, not every lead who clicks on a calendar link and scopes out a rep’s availability is going to end up scheduling a meeting. But that doesn’t mean that person won’t want to schedule a meeting later. As email marketers, this is where our nurturing instincts should kick in. Because if someone is taking the time to look at a rep’s calendar, they’re showing intent. So why not have an automated email go out to these exact people, asking them why they dropped off and if they have any questions? At Drift, we’ve seen first hand how sending these abandonment emails can help us save meetings that otherwise would have fallen through the cracks.

3. Send emails to anonymous leads who leave your website before starting conversations.

Speaking of abandonment emails, you can apply the same principle to website visitors who abandon your website before talking to you first—including anonymous visitors, provided they match your target criteria. Using IP address matching technology, you can identify what companies anonymous website visitors work at and, if it’s a company that would be a good fit to buy from your business, you can send them a cold email and ask if they need help with anything. At the end of the day, these are people who have taken the time to visit your website and look around, so even though they haven’t started a conversation with you yet, why not be proactive and take the lead? (FYI: We ran this experiment recently at Drift and saw an 80% open rate and a 15% reply rate, which is way above the average cold email reply rate of 1%.)

Email Database Hygiene

How do you keep your email list up to date?

It’s easy to get caught up in the vanity metric of 10,000,000,000 emails in your database. But what good do those 10,000,000,000 emails get you if only 25 of them are up to date, accurate, and landing in the inboxes of real humans on the other side? Many executives will ask, “How much did our list grow this month, quarter, week, day or hour?” Growth is a great measure as long as you take a Marie Kondo approach to your database. For all the emails you acquire you should also ensure you have a process in place for removing those email addresses that are bouncing, out of date, not responding, or have never taken action on any of your emails in a timeframe that feels right for you. For example, this timeframe could be if a person hasn’t opened an email in the last 6 months, you consider purging these addresses from the database.

One of the best kept secrets of these email addresses that never open or engage is that they may be telling you who you should be trying to communicate with instead. Often an email address goes “dead” because the person has left the company or may be on vacation or on parental leave. However, the automated responder instituted by most businesses typically will inform you on who you should be trying to talk to instead. Even better, the person the autoresponder provides you with is often higher up in the business and more than likely the person’s manager. If you’re like most marketers we speak to, you have a junior member of your sales or marketing team sift through all of these autoresponders maybe once a week to ensure you catch any actual replies to your email. In doing this you are actually throwing leads in the trash. Using an AI tool like Drift Email, you’re able to automatically mine this data, add it to your CRM and then flag these contacts for your business development team to work. You would never throw any of your other leads in the trash, so why are you doing so here?

Thanks For Reading

We hope you’ve come away with some new ideas you can use for adopting a more modern, conversational email strategy. And don’t worry: If you ever need any help getting things up and running, we’ve got your back.

If you’re serious about maximizing the output of your email marketing program you need to look at Drift Email. It’s hands down the best personal assistant your email marketing program will ever have.

Let’s chat about how Drift Email can help you take your email game to the next level. Click here to check it out.

The Ultimate Guide to Email Marketing

Fine tune your email marketing strategy and up your conversion rates. Get the guide now.