Integrate Your Email Marketing

by Will Francis

Posted on Oct 28, 2022

Email marketing has been around for a while, but it’s still the ideal channel to span the entire marketing funnel. And it’s free!

In this episode, host Will Francis talks to Head of Digital Marketing at Drift, Caitlin Seele, on how we can integrate email marketing with all other strategies and keep it as part of the overall conversation. They chat about subject lines, smart scheduling, and A/B testing, as well as logistics of aligning internal strategies to nurture tactics throughout the funnel and how to exploit the new reality of first-party data.

A full transcript of this episode is available below. 

The Ahead of the Game podcast is brought to you by the Digital Marketing Institute and is available on our websiteApple PodcastsSpotify, and YouTube.

You can learn more about Drift on their website, Twitter, LinkedIn, and on their podcast, Conversation Starters.

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“You should write like you speak, no matter who your buyer is, because at the end of the day, everyone's a person.” Caitlin Seele, Drift
Integrate Your Email Marketing

Top 3 Tips - Email Marketing

Caitlin offered her top 3 tips for your email marketing.

  1. Read your email templates out loud, and make sure they clear and to the point. Write like you speak.
  2. Look at the audiences for your email programs. Are the CTAs and offers relevant to them or just what you want to promote?
  3. Use email as a channel that's going to help you nurture leads after the point of conversion, and use experiences and content that can re-engage people.

Podcast transcript

Will: Welcome to "Ahead of the Game," a podcast brought to you by The Digital Marketing Institute. I'm your host, Will Francis, and today I'll be talking to Caitlin Seele, all about email marketing and its role in integrated digital marketing campaigns. Caitlin is Head of Digital Marketing at Drift, conversational marketing platform, best known for its chatbots and widgets that you'll see all over the web, as well as a suite of other innovative marketing tools. Caitlin has been in the game for over a decade, working across all digital marketing channels, predominantly for software companies in the U.S., and also in the UK. Caitlin, welcome to the podcast. Let's start by just explaining where we're at with email marketing. What's happening? And what are the trends that we're seeing in this space?
Caitlin: For sure. So, email marketing is one of those channels that it's been around for a very long time, in terms of channels that marketers are used to and have worked with across the world, right? But it's changed a lot, and our use of it hasn't necessarily kept up with that pace of change. I think more than ever, marketers in different businesses around the world are trying to engage with all of their buyers and customers online, right? You know, they really wanna to get in front of and directly to, you know, their target customer as much as they can, and email's a great channel for that, because it goes exactly to your desired recipient, at that right moment of intent. But we're seeing that one of the big things that's changed with email is that a lot of companies aren't necessarily thinking about it as a piece of their broader overall marketing strategy, or how it connects to the kinds of messages that your buyers are getting from other channels. It kinda makes email more of, like, a one-off point of engagement, when it, I think, could have a lot more potential when you connect it to a broader campaign or message.
Will: Right. That's interesting. So, do you think that that's just a widespread mistake that a lot of marketers are currently making it, using it as this kind of standalone megaphone, to just blast messages out there?
Caitlin: Megaphone's a really great word choice to describe, and I think we can all relate to it, right? If you were to open your inbox at any point in time, whether it's your work email or your personal email, I think we can all see some pretty clear examples of, just really generic, one-size-fits-all messaging, right? And if anything, one thing that's really changed, you know, since 2020 and over time is, buyers crave a certain level of personalization. You know, they really wanna be seen and understood by your brand, whether that's, you know, a business-to-consumer brand, like Netflix, or a television streaming service, right, that's recommending personalized, curated content to you. You know, a music or audio platform, right, like a Spotify or an Apple Music, you know, they're really delivering curated content, playlists, recommendations for you.
Buyers are starting to expect the same from B2B brands. You know, they have a very certain pain point or problem that they're trying to solve. And they wanna really hear how you specifically can help them solve or learn about that very specific problem. So, an email that presents a tons of opportunities to really nurture your prospects, you know, ask thoughtful questions, even in an email, in terms of, you know, does this topic resonate with you? Right? Do you have any questions about this offer or this webinar that you've attended with us recently? It enables you to kind of take your email programs from a promotional channel for your offers and your content and your campaigns into more of a true conversational channel, so that you can really be engaging with your buyers and prospects at a one-to-one level, with just a much higher degree of personalization.
Will: It's interesting that, isn't it? Because that seems to me to reflect this big macro trend that we've seen in recent years of a move towards more customer-centric behavior, really, on the part of brands, where, rather than yeah, this kind of, the traditional brands just shouting down at people, it's really putting the customer in the middle, and making them the kind of center of this, I guess, hub of conversations happening across social and email and elsewhere. Do you think that's basically what's happening?
Caitlin: I couldn't agree more. You know, I think that, you know, that year the whole world locked down was really the impetus to, like, action on that trend, which has been building for probably the past decade, I would say, in terms of people really wanting to feel heard and seen, and have that kind of more conversational marketing component, regardless, if it's an email an ad, an event, whatever kind of marketing you're doing. I think when we all had to move to purely digital channels, that kind of really required us all, as marketers, right, or anyone in a go-to-market role, to really adapt. You know, how are you gonna use your email channel, knowing that you no longer have the physical events you once did, to engage with your buyers at that one-to-one level? And now that, you know, we are doing some things in person again, and able to travel, you know, and kind of connect with our buyers and our customers in the "real world," if you wanna call it that, that doesn't mean people no longer want to hear from you in the digital channels. They're really turning there first, still, now more than ever, as their first touch point with your brand, so you wanna put your best foot forward on all those channels, even more now than before.
Will: Absolutely. I like the way you use the words "heard and seen," actually. There is that sense, isn't it, that the people want to feel, yeah, just that acknowledged, heard and seen, I can't really put it any other, any better way, really, rather than just made to feel like one of a million, just this kind of faceless mass of the audience, you know? And you're right. Personalization can definitely help with that. So, just thinking, you know, about the kind of broad marketing strategy, where does email kind of fit in, in the various stages of the marketing funnel, in your view, today?
Caitlin: I think email is one of the few channels that can really span the entire marketing funnel, or customer lifecycle, whatever you call it. From your very first interaction with a brand to, like, when you're talking with the sales team, right, to your purchase point, and then afterwards, to your onboarding and kind of expansion opportunities as a customer, email is one of those channels that's very uniquely suited to deliver a relevant, timely message, no matter where you are in that journey, and to really almost, like, hold your hand as you go through it, right? Introducing content that would be relevant, and useful, and helpful, right, to a buyer at that specific stage. And also, it's very uniquely suited to incorporate everything you're learning across all the other channels as well. You know, if you're seeing a certain person is really engaging with a certain topic of content on your website, email's a great channel to build in some automation, to send them more on that topic, right? You know, and kind of adapt to everything you're learning.
Will: That's interesting. I've got a question for you, actually. I'm curious about this. You know, there's, like basically two, in terms of time, there's two different ways to send people email. There's send everyone a newsletter on the first Tuesday of the month, so, you know, everybody's on the same schedule, and then there's lifecycle email, where you send someone email in relation to the day that they signed up, or first downloaded your lead magnet, so, you know, three days later they get this, a week later they get this, a month later, they get this. Do you have an opinion on if one of those is the right way to message people through email? Or is it a blend of them, or?
Caitlin: I think it's gotta be both. If you kind of put yourself in a buyer's shoes, right, you know, they wanna know about the most relevant and helpful content to them at the point where it's going to be most helpful. So, for example, if you're putting on, like, a really huge event, right, or a really important webinar, that has a specific date to it, it makes sense to invite everyone who would be, you know, potentially interested in that event at the same time, really close to when that event might be occurring. That's kind of the classic playbook you might run for, you know, webinar, or event invitations, follow-ups, reminders, that sort of a play. I think those sorts of offers always have to have a really time-based component to them.
However, outside of that, you know, personally, we don't do a lot of, you know, you might call it, like, a blast marketing play outside of those sorts of offers here at Drift. We've really built our email program to be very, like, action-based, based on when someone's actually taking action on your website, and then enrolling them in kind of a progressive, nurturing program, which, send date is going to be dynamic, based on when they're engaging with you, and also where they're located. In terms of different time zones and sending like that, you know, it's really easy to scale things like user-friendly time zones, depending on where you're located. Different kinds of spelling, right? Languages, even, or translations can be really important too, and you can accomplish that in a nurture program much better than you could in some sort of a one-off offer.
Will: Yeah. So, yes, you're right. So, in terms of nurturing leads, that specifically really is all about, as you call it, an action-based, triggered email. Okay. So, let's just zoom in on that middle of funnel a little bit more. What tactics would you recommend someone deploy for nurturing leads? Let's say I'm gathering leads through, like, free downloads of templates or something on my website. What's the best way to go about nurturing those people over time, do you think?
Caitlin: I would really start with kind of taking a look at your audience, and how you're gonna define that middle of the funnel, for you and your business. Every business is different. A really common way to do it is kind of to start to understand, okay, what are the kinds of content offers, landing pages, right, that might represent someone is at that funnel stage? Is it a certain template or calculator that you might have available to help people quantify the value of a solution like yours, right, or start to use it at some basic level? Is it a case study? You know, people who are learning and reading about what your customers are doing and where they're sharing success? And you can start by identifying, you know, okay, what are the two to three conversion points that are most influential at that middle-of-the-funnel stage, and then start there with your nurture program, right?
Think of a series of, like, say, two to three emails, maybe space them out one a week, that are gonna get a follow activity on that conversion event. So, it kind of adds that element of, like, recency, based on the buyer, again, making them feel seen and heard of, "Oh, yeah. I did do that," right? I engaged with that piece of content, I took advantage of that offer, and now the company is trying to help me understand how I could even get more from it, or use it perhaps, or share it with my team, right? And when you're building a nurture like that as a marketer, you know, say it is, like, a very kind of straightforward email program, where you're gonna send one email a week for the three or four weeks following that conversion event. Make sure you're talking to your sales team too, about what are they doing to follow up with the people who also download that conversion event, so that your nurture programs are very complementary to each other.
It can be very frustrating as a buyer, if you're getting, like, a set number of emails from a marketing team, but then you also have someone from sales reaching out at a very similar cadence, with very different messaging and offers. There's oftentimes a lot of opportunity for you to just simplify everything, with, like, one nurture program, that might appear to be sending from your sales rep, right? You're kind of killing two birds with one stone, so to speak, right, or accomplishing two goals at once, when you kind of take that broader view of, all right, if the real goal is to engage people who downloaded this conversion event, what is that gonna mean from a marketing email program, and also, a sales follow-up email program?
Will: Yeah, that, suppose that just means marketing and sales have gotta kind of get along, and work well together, and, you know?
Caitlin: It's hard to do.
Will: Hello. A quick reminder for me that if you're enjoying our podcast series, why not become a member of the DMI, so that you can enjoy loads more content, from webinars and case studies, to toolkits, and more real-life insights from the world of digital marketing. Head to Sign up for free. Now back to the podcast.
So, let's then talk, think a bit more about how that integrates with other channels, like, how, in your work at Drift, how do you see what we've talked about, that nurturing of leads and using email as a channel, how does that best integrate with our other digital marketing channels, do you think?
Caitlin: Great question, and I think it really starts with thinking about and considering the different kinds of tactics and email programs possible, when you're planning a campaign, right at the very start. So, say you might only have, like, one campaign that runs throughout the course of the year, or maybe you're an organization with, like, 20 or more campaigns running every single quarter. Whatever your team structure is like, you really wanna kind of think through, like, all right, conceptually, what audience are we going to try to reach for the next foreseeable point in time? What's the messaging, the offers, the campaigns we're going to engage them with? And start from there in terms of where is the email channel best suited, and how can I amplify the work being done in other channels with an email program, right? Or a nurture program, or something of that nature.
A great example would be, you know, say you are going to publish a really influential report for your industry, right? Maybe you're in the process of collecting some third-party data, or running surveys and polls, to really understand what people in your industry are wanting, and what their challenges are. Maybe, you know, you're planning to do some advertising, or social media outreach, you know, around that report or offer. You could insert the email channel there, to not just promote, right, the end report and offer itself, but also to re-engage and nurture the people who are gonna download it through all of those other channels combined. A lot of marketers skip that step. They kind of assume, like, all right, I'm gonna use email to launch a certain campaign, right, or communicate a certain message at a certain point in time, and they kind of skip over email's big super power to re-engage and nurture people along a customer journey, and don't necessarily, like, think that post-conversion experience through. That's where you're gonna start to see a lot more ROI, not only from your email program, but also from your campaigns holistically, because you're able to, like, extend the life of that conversion, that event, that point of interest.
Will: Yeah, and I suppose, you know, on paper, if I'm understanding you right, on, you know, like, when you think about the cost of this, to once you've got someone's email address, to reach them whether they've converted or not, you know, leading up to conversion, to every time you reach them is costing a fraction of what it would cost to repeatedly reach them through other channels.
Caitlin: Exactly. You know, email's free, right? You know, once you've kind of gone through that work, to kind of get people interested in your brand, and you have that email address and you can market to it, which is certainly another piece of the email channel, for data privacy and its impact there, email becomes a no-brainer.
Will: That's an interesting thing, because I'm gonna, you know, stab a wild guess that you guys at Drift are kinda of all set to capitalize on the boom in interest in first-party data.
Caitlin: Definitely.
Will: Right. And we've, our listeners have heard plenty about this. We've done episodes about it. But for anyone who doesn't know, long story short is that using third-party data to identify and reach our audience is gonna get harder, for a variety of reasons, most notably because the big web browsers are going about the process of phasing that app technology out. So there's more pressure on marketers to gather our own data, rather than rely on people like Facebook and Google as a broker to reach audiences. Right, so, what are you telling people currently about a first-party data strategy, or approach?
Caitlin: I think it definitely changes how you would approach any kind of marketing, right? And email is very specifically impacted, because, as a marketer, you have to put much more thought and intention than ever when it comes to acquiring that email address, right? And to use a very marketing term, or the flip side of it is, to get a person out there in the real world genuinely interested in hearing more from your brand, right? Depending on the kind of language you wanna do...
Will: No, we've seen the tactics to do that change, because, you know, there's the "10% off your first order," and "download a free ebook." I mean, are the tactics sort of staying pretty much the same to gather those email addresses in the first place?
Caitlin: They really are, and that's, I think, a very frustrating part, not only as marketers, kind of, you know, seeing what other people are doing in the email channel, but also for your buyer and consumer. They're gonna get annoyed by those kinds of offers and that kind of messaging in the email channel, because they hear it nonstop, like a megaphone, to use that word, all day long. I think one way to change that script, or flip the narrative, can be to think of email as a channel to start a conversation with your buyer. And the funny thing is is that if you ask a question in an email, people will reply to you. It's something we've tested here at Drift, and it's something that's really helped us change our first-party data strategy, too, right? You know, if you know, say, someone attended an event, right, you could send a classic traditional follow-up email, saying something along the lines of, "It was so great to see you there. Click here to book time with our team to learn more."
Or, you could end that email with what we call a conversational CTA, which is asking a question and suggesting an action at once. So, you know, "What was your favorite session at the event? What did you think of the webinar? What's one best practice in this book that you're most excited to implement at your company? What drove you to download this?" And then suggest a next step, which could be, you know, another piece of content on the same topic. It could be schedule a meeting, "We'd love to talk about this with you." But people will reply. And in those replies, you can get a lot of data and information around, like, hey, their biggest challenge is X. You know what I mean? I'm gonna find a way to, like, document that and share it with my sales team, so that we get and can provide that kind of contextualized follow-up over time, in a way that balances first-party data needs with, like, real, actual, demonstrable behavior and action that someone's taken.
Will: Yeah, that's interesting. Could you record those responses in the CRM itself? Like, so that I could segment by that in future?
Caitlin: You can. Drift and other marketing technology platforms will offer, you know, technology to help you do that at scale, but you could definitely create a field, very similar to how your sales team might create a field, right, in their CRM. You know, after they get off a real call with a prospect, you know, they have some notes, they document what was said and done. There's certain things you can do in email, to look for certain keywords, right? Or your team can kind of document in general, right, if people do reply, it pops up in your real email inbox, and not, like, a no-reply email. And you can have someone in your team kind of filtering through the responses.
Will: Yeah, yeah. Because that's interesting, you know, it's an interesting opportunity, from my perspective, with first-party data, not just getting people's email addresses, but finding out their, just their preferences, or if I'm a fashion retailer, finding out, like, their shoe size, or their favorite color, or whether they're going on vacation this year. I don't know, just, do you know what I mean? And getting more of that kind of context that you can use to be more relevant to them, that's the more subtle stuff, really, I think.
Caitlin: Yeah, and there's tons of data out there from recent studies, too, that show, like, I think one study from McKinsey recently, which is, like, a large consulting firm, proved that buyers are 80% more likely to buy from brands that are delivering a personalized and relevant experience. The thought there is that they're really able to connect, right, what you're doing to what they're hoping to achieve, so it pays off, in terms if you are able to capture that data and turn it into increasingly personalized email nurtures, email campaigns, whatever the case may be, you're gonna get higher engagement rates. And, you know, in reality, what you're doing is just treating people more like people, in terms of how you'd have a conversation with them if you were together, sitting in the same room, right? You're not just that megaphone, spewing out messages.
Will: Yeah, that just seems to be something that's, I don't know, being talked about a lot. I'm an educator. Like, I lecture and run workshops about marketing all the time, and I feel like that's the thing I'm just trying to really change people's mindset around is, like, just stop shouting at people. You know, just talk to people. I mean, I used the example the other day in a copywriting workshop. Like, David Ogilvy said, in the 1950s, "Write copy like you would say it to someone, not like hyperbolic marketing-speak." I mean, he said that 70 years ago, and people are still doing it. It's crazy. But I think it's just what we think our job is, as a marketer, like, oh, I must get the megaphone out, you know, because I have to drive some results. And so, thinking about the way that we talk to people, is there a difference between the way that we ideally talk to people in email versus more conversational channels like social or, like, a website chat widget or something?
Caitlin: Yeah. Here at Drift, and, kind of, us, I've seen myself in my own experience working in, you know, the kind of the tech and marketing industry for 10 years now, there shouldn't be a difference. You should write like you speak, no matter who your buyer is, because at the end of the day, everyone's a person. So, you know, if you were to meet, you know... Say you're trying to target, as a marketer, maybe you're trying to reach, like, a chief marketing officer at a certain company. How would you talk to them if you met them in person, right, at a conference? That should be what your email sounds like. Some of the best compliments I've ever received is I actually went to an event here in San Francisco, where I live, recently. And someone said, "Oh, I think I'm on your email list," they send, like, from me. Right, from Caitlin? "Like, your email sounds exactly like you."
Like, they talked to me for a little bit at an event, like, that really sounded like you. It makes sense. And it should, you know? I'm not talking as informally as I might text my friends, right? You know what I mean? But you should always write like you speak, and that good old adage of just, "Read something out loud before you send it" can be a really good barometer of, like, okay, does this sound like whoever it's supposed to be sending from? You know? Is this really gonna resonate with a human, or is it just stuffed full of, like, jargon and industry terms that make it really laborious to read? People don't read things with much depth anymore, I don't think, in general, whether it's a website, an email, or what have you. So it's better to just be as to-the-point as you can be, and use the same language you would use if you were presenting at a conference or a trade show, to talk about your brand and your problems.
Will: Absolutely. Do you think that extends to email subject lines, which is something that I can't help but ask you about because you seem pretty well-placed to give us some nuggets of insight around that?
Caitlin: Completely. We have done a really extensive amount of A/B testing on subject lines, specifically here at Drift. I would say, across all of our email programs right now, we probably have over 100 of them running, like, live time right now, and to kind of test out what is that balance, and how does it vary for different kinds of personas that we might be trying to reach, right? And in general, our takeaways and some of the things that we've distilled and applied across all of those tacks is, again, write like you speak. People are people, they wanna be communicated with as such, so start there, right? Don't lead with the full name of a very long-winded, you know, webinar title. Distill it down to, like, the main, how you'd describe that topic generally, to just get someone's interest, because the goal is really just to get them to click through and learn more at that point, right? You don't need to provide all that information in this super-long subject line up front. We also find it works really well when you ask a question, and include data, or third-party touchpoints, right? Numbers. Seriously. Even if it's, like, the number five in an email, that says, like, you know, "5 best practices for" something, versus typing out the word "five," can make a huge difference.
Will: Or, like, "26% of marketers are doing this," or something like that.
Caitlin: Exactly. It adds, like, an element of social proof of, like, "Okay, that's an interesting stat. I wanna hear more." And it, again, makes it more skimmable when you have numbers, because people aren't reading the word "twenty-six": it can seem very obvious, but it works when you're using numbers, just to kinda break up that line of text. It catches someone's attention, enables them to really understand it quickly, and just get to the point of what is this email about, and is it gonna be relevant for me, and do I wanna click through?
Will: Someone asked me the other day, in a workshop, should they include the first name merge tag, you know, that dynamically populate the first name into a subject line? And actually, I didn't know. I wasn't sure what to say. What do you think about that?
Caitlin: I might have a controversial opinion about it, and that's that you shouldn't do it. I think that people are all too familiar with an email template that reads something like, "Hi, insert first name token, at insert company name token. I've heard you're a insert job title here." Oftentimes, your data is, A, wrong, maybe. B, or outdated, right? Maybe they've got a new job or a new role recently, and your data isn't updated to reflect that. Maybe you don't know it, because of first-party data concerns and everything you've got there. So, it renders oddly for someone, and makes them feel like you know even less about them than you probably actually do. And C, it just feels really generic at this point, I think, because of a lot of marketers are doing that. If you do wanna personalize a subject line, though, or an email copy, I always recommend doing it based on, like, behavior and action that someone's taken. That's oftentimes way more reflective of what they're actually gonna be interested in and what they're gonna click on, right, if that's your desired outcome as a marketer.
Will: "Still enjoying our social media content calendar template?" or something like that, you mean?
Caitlin: Exactly, right? "Did you enjoy speaking with us in, like, the city you were in at a certain event?" Right? "Do you wanna learn more best practices about this topic," that they just downloaded an e-book on? You can create the same kinds of dynamic fields and values in your marketing automation platform that you would for, like, first name, right? It could be topics of interest. And maybe if you download, like, a account-based marketing e-book, say, on a website, maybe that value changes to ABM, and you could insert that value into, like, an email body or subject line, or just develop a customized program for that topic, if you know it's valuable for your business. That's gonna feel much more genuinely personalized, in a very contextual way, and less like, "where did you get this data? How do you know my name?" You're gonna get way less of those kind of annoyed responses, and more, like, "Oh, yeah. That is genuinely interesting and helpful."
Will: That's good. I mean, I agree with you. I leaned towards that, because my response was, well, if you look at the biggest ecommerce brands on the planet, like Nike, Assos, etc., they don't do it. I've really noticed that. Like, by and large, they don't do that. They don't put my name in the subject line. And secondly, yeah, do I really trust the tokens, as you call them, or the merge tags or whatever? Not really, you know. Yeah. So, that is very interesting. I suppose, following on from that, because yeah, I didn't, you know, you really are kind of doing this, testing this stuff at scale, so I'll dig in a bit deeper. What are you finding about the actual content of emails, like, in terms of length, in terms of content, whether images and text, or just text, keeping it really plain? Are there any kind of patterns that you're seeing there, that work particularly well in the content of emails?
Caitlin: That's a great question, and I think the unhelpful answer is that honestly, it's really gonna vary, depending on what industry you're in, right, what the offer is in question? You know, that's really gonna vary, in terms of should I use HTML? Should I use plain text? Like, if you're sending a newsletter with a ton of different calls to action in it, you're probably gonna benefit from, like, a longer-form HTML-style email. But, holistically, on aggregate, I think centering back to this kind of big finding that we've had here at Drift, and kind of see with a lot of our customers or other marketers out there in the world, is that, at the end of the day, people wanna be treated like people. And we've seen that a simple, plain text email actually can way outperform an HTML-style email, because if it's written like you speak, it can seem much more genuine, and like a real email, right, than something people open immediately and say, oh, gosh, it's a catalog, it's a newsletter, delete, delete, delete, delete.
So, for some times and some cases, I really recommend start A/B testing plain text versus HTML, and you might be really surprised. Especially for things like a webinar invitation, a campaign launch, some of those more straightforward messages, that don't necessarily need a lot of text to them, test that out. Start there. We've seen really incredible results in a lot of different use cases from just making that switch to a plain text email alone, and the bonus it's gonna save your team a lot of time, being able to just write plain text emails and schedule those, versus designing a comprehensive HTML template.
On the flip side, though, I think anything you can do to make your emails more skimmable is gonna work really well too. Because in reality, people are usually reading their inbox on their phone, right? Maybe while they're commuting, taking a break, they're kind of scrolling and skimming through. You wanna design your emails with that actual behavior in mind, right? So things like line breaks, almost like you're writing a movie script, can be really helpful because it's built for that level of skimmability. So, including, again, things like numbers, bullet points, really adding those intentional paragraph breaks between sentences, help people digest the content of your email very quickly, and it's gonna make you write shorter-form copy as a result as well. So, just practice, again, getting to the point. You probably don't need five sentences to describe the content of a certain e-book, right, or the topic of a podcast episode. You probably should be able to do it in one sentence, two sentences max anyway. If anything, this is gonna be a forcing function to make sure you take a look at that in your copy editing process.
Will: Yeah, true. And you're right. It depends, doesn't it? I mean, I see a lot of creators who use platforms like ConvertKit. They send Neil Patel. You know, if you subscribe to his email, like, it's completely plain text, because he's sharing knowledge, someone like that. You don't need pictures. Whereas obviously, if it's a fashion brand, someone like Nike, then yeah, you wanna see the product, you wanna see models wearing the product. But, again, it's incredibly minimal, and it's straight to the point, and pithy.
Caitlin: An image speaks a thousand words, too, sometimes, right? So don't shy away. Even if you are sending a plain text email, you can still use images in a plain text, like, email format, right? Or a link to a video, or whatever you might be talking about. But again, whatever you're doing, HTML, graphics, whatever, keep the copy really short.
Will: Yeah, yeah. Absolutely. I suppose at this point, I have to ask, do you have any examples of brands, maybe brands that use Drift specifically? Do you have any case studies essentially, of brands that are doing this particularly well? And anything that you can talk about, specifically, that they're doing well?
Caitlin: Immediately what comes to mind for me are the brands that seem to be thinking about email as just one touch point in a broader experience they're trying to build with you, and are very contextual, again, based on that moment, intent, and actual behavior. A great example, you know, here, for me, personally, right, in kind of that business-to-consumer, B2C world, is, I do a lot of my grocery shopping at this grocery store called Whole Foods. And somehow, someway, they definitely know what I've purchased, and recommend to me in email recipes that involve ingredients I tend to purchase often. And I've actually made a ton of them, and have subscribed to their recipe newsletter, as a result of getting that email communication. They've definitely, you know, built a really strong pattern of engagement with me, right? And I shop there, so, it's worked, in terms of that email being very contextual, versus, you know, spammy about a sale, or maybe a promotion they're starting to run. I do get those too.
But a lot of the communications I get from them are very intentional, and I appreciate that. And I think there's no reason why you couldn't do something similar, again, if you were a B2B company, too, right? If you know someone's visiting a certain landing page over and over and over again on your website, you could probably recommend related content to them, to kind of get them to take that next step beyond that landing page, right? You know, if they're revisiting a certain book, you know, maybe they've got it bookmarked, right, because it's so useful, in their browser or a tab, you can certainly think about how you could use email to be recommending related resources and content to them.
I also think that brands I really admire in the B2B world, one of them that's top-of-mind for me would be Gong, like, a sales technology provider. They do a great job of not only really practicing what they preach, and writing an email like you speak. It's very conversational, it's very useful, it's very helpful. But then that same messaging and language is carried post-click. So, when you visit their website, and you see the chat conversation that pops up on it, it's the same kind of messaging and problem statement that you clicked through on on the email. And that's just a great user experience, in terms of when you click through, just immediately being, like, okay, I'm in the right place. This is what I expected when I clicked through, right? The message match is there. And then a conversation you're starting with me in chat or conversational marketing on the side is also on that same topic. And maybe there, you are greeting me by name, because you know I clicked through on a very specific link on an email. Just a very seamless, frictionless user experience.
Will: I could imagine B2B companies specifically struggling with that, you know, because they might say, right, we've gotta write our emails nice and conversationally, but no one's addressed the fact that their website's still really stiff and corporate, and it obviously be an obvious kind of, you know, jarring disconnect when we send people to the website. So, that's a really good point, actually. You know, landing pages absolutely do need to kind of, you know, keep that consistency. So, I'm curious about what Drift does, because I know that, you know, I know about Drift predominantly for the on-website chat functionality. Is I right? Is that what most that was what the company became famous for?
Caitlin: Kind of. Yeah.
Will: And then it's kind of broadened out into a suite of other products. So, how do... What do all those don't have to be too comprehensive, but, you know, what do all those other things do, and how do they kind of augment... Because you've hinted at some stuff like if someone visits a landing page, you email them. How do you do that? It must be some tracking technology, it'd be cool to just hear a little bit of a fleshed-out picture of the other things that Drift does around the edges, that kind of maybe bring it all together?
Caitlin: Certainly, yeah. So, Drift is a conversation cloud platform, which means that we help companies start conversations with their buyers in the moment of intent. So, while someone is on your website, right? While they're reading your email, while they're talking to your sales rep, we wanna be able to enable you as a marketer or a salesperson or a service, really, anyone at your business, to just start a conversation with someone there. So, again, you can engage that buyer while they're thinking about you and while you're top-of-mind, understand what brought them there, to that conversation, and recommend the right next step to them.
We do that through a pretty wide variety of solutions. So, conversational marketing, chat, you know, kind of what you mentioned. But also conversational sales, of if they are on an email reply thread, and they're really responding, getting back to you, you wanna loop in a sales rep as soon as possible into that conversation, to kind of help get them that right information, and, you know, really, again, understand and recommend how you can help.
We've helped thousands of companies do this. And, you know, I think whether you are talking about chat, you're talking about email, any of the marketing channels, you can apply that concept of how could I use this marketing campaign to start a conversation with somebody, right? And how am I gonna do that at some degree of scale? We do offer some email functionality and tools as well, that, again, if you do get replies to your emails, we can, you know, capture that data and feed it in across your digital marketing tech stack in a scalable way, so you can provide those kinds of personalized multichannel experiences. As kind of the next step, you know, once you are kind of moving forward with that more tailored email nurture strategy, it's a great next step to make sure it's all connected.
Will: Yeah. I see. Yeah. So, a bit of kind of technological glue, to create more seamlessly personalized journeys for people, I suppose.
Caitlin: Yeah, and just, you know, generate more conversations overall, right? You can kinda really engage that passive traffic you might get otherwise to your website, right? You know, you can start more conversation with your buyers, which leads to a lot more pipeline and revenue for businesses. Because you can jump in a lot sooner, and before they might reach out to you to get a demo, right, or request pricing, or any, learn more about your product, you can certainly use Drift to really engage them, and start that conversation way earlier on in the customer journey, and then provide a great, you know, tailored experience thereafter.
Will: Yes. Absolutely. So, you're head of marketing at Drift today, and you've really worked your way up over the years, from, all the way from being a marketing intern. What have you learned along the way about building a career in marketing?
Caitlin: Yeah, that's a great question. I think that one of the most important things I've learned, right, through my own career is to have a goal. And when you're deciding whether to undertake a project, or change something, or do something, always think about it like you're shooting towards a target, of, like, is that, you know, going to help me achieve this goal? Or is it something that would be really interesting, but maybe very unrelated to what I'm trying to do? And I think that's true when you're at work, right, thinking about should I build this email program? You know, is it gonna help me accomplish this end goal I have of generating a certain amount of pipeline for the business? Or professionally, right? You know, hey, if I really want to lead a digital marketing or demand generation function, what are the kinds of skills I'm gonna need to really achieve that goal? And what might that mean in terms of professional development that I might need to seek out, right, things I might need to learn? Questions I wanna ask, that are gonna help me get there, versus maybe some side projects that you can end up getting really distracted by.
I think having a goal is a great place to start. And with that, just, like, being curious. You know, recognizing that you need to learn and grow every single day. No one knows all the answers 100% of the time, right? Especially in digital marketing, where things are changing every single year, in terms of what technology can do, what kinds of experiences to provide, you've gotta stay curious, and always wanting to learn from what's out there, also the people on your team, other people at your company, kind of, your network, you know, podcasts like this, seeking out those learning moments, to kind of help you challenge yourself, in terms of am I doing this just because it's how I've always done things? Or am I doing it because it's actually gonna be aligned towards the goal, and kind of in line with trends happening in the future?
Will: I think that's what keeps it interesting. I think marketing naturally attracts curious people, because, for me, it would be really boring if it was always the same and it wasn't always changing, right?
Caitlin: Completely. It's the best part, right? Yeah.
Will: Yeah, of course it is. But I think the flip side is, because there's no, like, one marketing manual, that's, like, gathering dust over the decades, and has always been the same, there's no, like, one static way to do marketing. I do think that it's also an industry that's plagued by imposter syndrome, because you never really know if you're doing it right, and you never really know, like, am I the real deal, or am I just faking it, or what? I mean, was there a point in your career where you suffered from imposter syndrome? And was there a point where, you know, you overcame that, or you may not have done yet? I mean, who knows, but...
Caitlin: Certainly. I think, I assume a lot of the marketers out there would agree in terms of imposter syndrome is something, like, you know, I've certainly been challenged with over my career, right? And I think, you know, a lot of other people have too. One boss I had pretty early on in my career did a great job of kind of reminding me of, like, whenever you feel that way, take a step back, and look at the bigger picture in terms of the impact your work has had, whether you're looking at, you know, a data point from an A/B test you ran, where you're not seeing the point, and you're feeling like your recommendations are coming out of nowhere, ground it in data, always, and take a step back and just remind yourself kind of what you've really done so far. And it's, you know, a very reality that no one knows the answer 100% of the time, so don't hold yourself to that standard either.
The best you can do is kind of just make the best decisions you can with the data you have available, right? Seek answers to questions you don't know. Ask for help when you need it. But that's what everyone does, you know, kind of at a certain level of their career. And it, again, can sound really simple, but I think the imposter syndrome can build and build and build if you don't remind yourself, like, okay, the expectation isn't that I'm gonna have the 100% right answer to every question or situation I'm in. It's that you learn how to kind of navigate that situation, and, you know, seek answers from those who can help.
Will: Yeah, you're absolutely right. That was, I think that was really good advice actually, from that person that you worked with, about looking at the impact of what you're actually doing, the impact of your work, results of your work. We can lose sight of that. What advice would you give to an intern in 2022 looking to grow into digital marketing roles?
Caitlin: I think it would be to seek a role that's going to enable you to get exposure to as many areas of marketing as possible. You will never regret understanding, you know, how good marketing content is created, even if you're not a content marketer. Having spent time working in, like, a little bit of content marketing, public relations, event marketing really helps me today, as a demand generation and digital marketer, because I truly understand how the strategies can connect to each other, right? It's going to enable you, fast-forward 5, 10 years from now, which may seem, like, so far in the future you can't really think about it. That experience you build early on in your career is really going to enable you to develop more thoughtful, encompassing, integrated strategies.
Like, you know, having built so many nurtures and email programs earlier on in my career really helps me understand now, even as the world has changed, right, with this rise of personalization and first-party data, everything we've been talking about today, you kinda get the fundamentals enough to really recommend something very thoughtful, and also help your team, right? In terms of development, and how it might actually translate to actions or programs you can run. So, seek the widest variety of experience possible. It's okay if you don't like some things, you know. Happens to everybody. But that will start to enable you to understand, all right, here's what I love most. Here's what I'm really good at. How do I double down and seek more opportunities to do that thing, while still developing some skills you just need, right, to kind of move forward and advance in your career and other areas. There's certainly a bar with that, but, yeah, seek as much exposure to different kinds of marketing as possible, and, you know, ask questions to smart people.
Will: I absolutely agree on that, actually. And I think that these days, careers aren't as linear as they used to be. You know, so, if a fashion brand is hiring for a marketing manager, yeah, they don't necessarily just want someone who's only ever worked in fashion, and only ever done marketing in fashion. If you... People hire the... They welcome the difference. "Oh, you've worked in fashion, but you've also worked in TV. Hmm. Why is that interesting and useful?" And, you know, it makes people think. Or, "Oh, you've worked in marketing, but you've also worked in sales. How's that..." You know, and I do think that makes you a more interesting candidate, so I really agree with you there. I think that's a good point, good advice. 

What are three things that our listeners could do immediately after listening to this podcast episode, to get more out of their email marketing?
Caitlin: One, read your email templates out loud, and make sure that they sound like how you speak, right? Are they very confusing and full of jargon? Or is it very clear, direct, and to the point, is step one. Step two would be to really then look at your email programs and look at the audiences for those programs. Are you recommending CTAs and offers that are actually relevant to that audience, or just something that you really wanna promote internally? There's a big difference between the two. Sometimes it's the same answer, sometimes you are going to have that "megaphone effect," and you might not realize it, if you're just promoting what you wanna to promote, and not what might actually be useful to your audience.
And third would be stand up some post-click nurtures. You know, use email as a channel that's gonna help you nurture leads after the point of conversion, and think through, like, all right, if these are my top offers, it's these three, what are some really simple email nurture experiences you could stand up to really re-engage those people, and suggest, you know, kind of more helpful content to them? That'll help you, you know, really build more pipeline directly from your email program, right, and also just develop much more of a relationship with all of your buyers.
Will: Yes. Great advice. Thank you. Well, look, thank you so much for your time and your insight, Caitlin. It's been a really fascinating conversation. I've certainly learnt loads. So, I do appreciate that. I've just got one last question for you. Tell our listeners where they can find you and connect with you, and also find out more about Drift online.
Caitlin: Yeah, it was really awesome talking with you too, today, Will. You can always find me on LinkedIn, Caitlin Seele. You can email me, And definitely check out Drift. Our website's  . You can listen to us on our Conversation Startups podcast, which is wherever you might listen to podcasts, Conversation Starters. We really talk a lot about that rise of personalization, and kind of trends in marketing, so it's a really great spot to learn more about Drift, and also just hear from some really talented marketers out there.
Will: That's great. Well, thank you so much again, and look forward to one day chatting to you again soon. Thanks a lot.
Caitlin: Yeah. You too, Will.
Will: If you enjoyed this episode, subscribe wherever you get your podcasts. And for more information about transforming your marketing career through certified online training, head to Thanks for listening.

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Will Francis
Will Francis

Will Francis is a recognized authority in digital and social media, who has worked with some of the world’s most loved brands. He is the host and technical producer of the DMI podcast, Ahead of the Game and a lecturer and subject matter expert with the DMI. He appears in the media and at conferences whilst offering his own expert-led digital marketing courses where he shares his experience gained working within a social network, a global ad agency, and more recently his own digital agency.

Connect with him on Twitter (X) or LinkedIn.

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