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You’ve Grown Your Email List…Now What? – @bestofjess
The Agents of Change

Email marketing can be a tricky beast. It’s more than just making sure you have an email list that you’re spewing out x number of emails to a week. You need to finesse your audience, make sure the content is informative, compelling and eye catching, and allows you to stay front of mind without bombarding them to the point of unsubscribing.

Jessica Best has taught businesses how to do email the right way. Her decade of experience in email and digital marketing has allowed her to strategize for a diverse audience, while helping businesses improve their return on investment.  

Rich: Jessica Best is the Director of Data Driven Marketing at Barkley, where her business card says she exists in space between expertise and evangelism. In her nearly 10 years of email and digital marketing strategy, she’s worked to improve return on investment for a diverse clientele including Dairy Queen, Spirit Airlines, Farmland Foods, beauty brands, Hostess, Water.org, and Boulevard Brewing Company, just to name a few.

Jessica has spread the good word of great email marketing from New York City to Las Vegas, from Content Marketing World, to SXSW Interactive. Jessica lives in Kansas City and is an active member of the marketing community there, including being past President for the Kansas City Chapter of the Direct Marketing Association.

Her passions are good food, good people, and great email marketing. Jessica, welcome to the show.

Jessica: Thanks. Thanks for having me.

Rich: So I was checking out your LinkedIn profile earlier, and I understand that you have a conversational language expertise in French. How do you say, “Join my email list” in French?

Jessica: Rejoindre ma liste de email…maybe? 

Rich: That sounds about right. It sounds romantic, but it’s probably not the best way to get people to sign up. So you seem very passionate about this whole email marketing thing, what drew you to email marketing?

Jessica: You know, it was kind of an accident, actually. The very first time that I came in contact with email marketing was I had just started a job where I didn’t really know how to do any of the things that I was assigned. I was hired because I was a client’s vendor relationship before, and they hired me away saying they were going to put me on direct mail and this new thing “email”. And I didn’t have very much experience with how to do any of those things, and they assured me that that was not a reason to not accept the job. And I learned it all kind of on the fly.

I had basic marketing principles, I had gone to school for strategic communications, I had taken some marketing classes and psychology classes. But what they really taught me was the idea of database marketing, using a direct mail list. People who have purchased tickets to a theater show in the past are more likely to purchase tickets to a theater show in the future. And so using the information I had actually informed my marketing. One of the big pieces of that, obviously, was email. Because it was so much more cost effective than – at the time – direct mail, catalogs and things like that.

So I kind of got to learn email marketing accidentally. After about a year and a half I joined an email platform company right here in Kansas City, called emfluence, and that was when the real geekery got turned up to 11 on the volume knob. I learned how to do email the right way – not to say I didn’t do some things right on my first go – but I certainly learned some of the things I was doing wrong. But that was where I really learned the way that email really moves the needle, things I can test and try with hundreds of different clients and learn that email has progressed from this tiny thing in 2008 to today.

It’s been a real long-term love affair for me, and I think the reason I get so excited about it is not only can I use data to inform it and to make it more relevant to the people I’m sending it to, but I especially get excited about what the data can tell me about how it performed.

So I came up in a world where media is really the king, TV and radio. And I saw this opportunity for an area of marketing where I can prove every dollar that an email made for my company, and I was hooked. So it’s a long-term love affair, like I said, but it’s still being written on that.

Rich: Excellent, so that’s your journey. Now you mentioned almost in passing that you had made a few mistakes in your first go round. What were some of those mistakes, and how did you overcome them?

Jessica: Oh boy. Well some of them are all together terrible ideas that I just didn’t know the repercussions of. So one thing that makes me cringe thinking about is, was we actually used purchased lists. And this has been a number of years ago.

Rich: Sacre Bleu!

Jessica: I know, fire me on the spot, right? But again, it was that logic of if somebody has been to a theater show in the past, they go to a theater show in the future. And for us that meant any theater, not just our own theater. So we had our own list of ticket buyers. Of course, here’s my other mistake – confession time – I was also automatically adding anybody that purchased tickets to our list without asking them. Which of course in 2016 would be a “no-no”, as well. Certainly they were not shocked to find emails for future shows in their inbox.

But let’s say they got tickets to the ballet for years and they’ve never even heard of the theater company that I was with, they’re usually surprised to get my email in their inboxes. And while surprises are good in life, in email marketing they are a bad sign, it’s usually the first reaction people have before they hit the “spam” button.

So those are my worst two, those are the things I tell people consistently not to do today that I have to admit every so often that I have done once in my career.

Rich: When I first started my email list for flyte new media all those years ago, I started my list by just taking all my clients and putting them on that list. At the time, there really weren’t a lot of rules against things like that, and people weren’t getting so much email. I’m not saying that made it right, maybe it just meant nobody complained. So the rules that were available then are obviously much more different than what we recommend today.

Jessica: They are, and that continues to evolve, and it’s different by county, and it’s different by industry really. I mean, there are some business to business providers that can completely justify sending to a list of people that have not given them explicit permission, and then the United States says that’s okay. In Canada it’s not, but if you’re only emailing your demographic and your geographic region, then at least these people know why you’re sending them email. That factor of surprise is really when you get into trouble. 

Rich: Absolutely. Now a lot of the focus when it comes to email marketing is on list building. Obviously very important, less is said about how to do email marketing the right way. So we’ve talked about a couple mistakes you made and how you overcame them. But what are some of the other things that you feel are important – and possibly missing – from email marketing, especially as it relates to small businesses?

Jessica: Great question. And this is one that I feel like my answer changes perpetually because there are things I see that really move the needle that become more widely adopted. And the first thing that I think of is a Welcome email. Even in a small business, whether your business is a consumer product or business, or business to business, everybody needs that first touch. And the biggest opportunity as a marketer is, if somebody’s asked to receive your email – they’ve opted in on your website – or because of a promotion that you’re doing, they’re at least semi interested. Don’t just go on a first date and say, “Well that was really nice.”  What’s the second date? Ask them on a second date.

So that welcome email can be a chance to – even if it’s a simple “follow us on social” – that a lot of times it’s “now start shopping online”, or just reach out to them and invite them to call if there’s anything you can do to help them. Take that next step. Not everybody is going to say, “yes”, but the worst they can do it delete the email. They’re probably not going to unsubscribe, they’re at least interested enough that they just had their first email from your company.

So the welcome email is more pervasive, which I love. I think it’s really important but then there are little things that are sort of baffling to me that have not become as pervasive. And one of those is something called the “pre header’. This is actually kind of interesting to describe verbally instead of showing. But the gist of it is it’s the very small type that’s at the top of the email that is true text before you get into a lot of the graphics that sort of start a traditional email.

And the reason for that is – and usually it says something like, “If you can’t see this email click here” – that text is what pulls into the inbox in something called a “snippet”. In Outlook, in Gmail, on Android and on iOS devices – including the iPhone – you get a little bit of the first text in the email that shows up in the inbox as you’re skimming your inbox. In fact, on an iOS device, it’s twice the real estate of the subject line. So you see who it’s from, you see the subject line – which is usually truncated about 20-24 characters on a mobile device – and then you get two full lines of preview text of what’s in the email. ”Snippet text” is what they call it. 

So if you’re just using that pre-header text of “if you can’t see this email please click here”, that is unfortunately what’s showing in the inbox. And there is so much opportunity in making something that really dances with or works well with your subject line to drive up your open rate. Because, “if you can’t see this email, click here”, is not really doing a lot of heavy lifting for you here.

Rich: Should we be teasing the content of our email to get them to open it, and have some sort of mystery or interest to get them to click on that “open” button?

Jessica: Absolutely. It’s kind of a good headline. Subject lines especially, but subject lines and pre-header combinations are a headline/sub-headline dance. You might see that what you would normally tweet as a takeaway from the article or content that you’re sharing, that makes a pretty good length estimate for what your subject line plus pre-header should equal in total.

So think of it as that’s your one shot to entice somebody to read the email that you have to offer them. And make sure that if you have a discount or a promotion, put that right in the subject line. I see so many people have great offers and their subject line is something really clever instead of really clear about their offer. And I blatantly steal this from a gentleman at MECLabs, but clarity trumps cleverness when it comes to email marketing. If they don’t know why to open it, then it doesn’t matter how clever it was.    

I would say enticing is great and a preview is great, but you want to be really careful not to be tricky. And I think that’s maybe the line that a lot of people cross. That’s for Buzzfeed, leave that out of your emails. It might work once or twice, but eventually people will stop responding to it. And unfortunately, you may have lost them forever.

Rich: It seems to me that this subject line and pre-header are not dissimilar from the search engine results with the big blue header and then the meta description underneath where you need to be clear, you want people to click through – or in this case, click “open” – and then you give them another snippet of language/text to give them more reason to open it up. I’m sure there are many psychological techniques that you can use to make it seem more enticing for them to open it.

Jessica: Exactly right. And I love that you talk about the psychological mechanisms, because that’s one of the big things that are underutilized in email marketing, and marketing in general. Sometimes when we test a subject line to see whether one works better than the other, we get into a trap of testing the words and not the mechanisms – or motivators. So if urgency works or the sense of joining a community or a sense of competition, if there is only so many available and you have to hurry, there is kind of an urgency and a rarity draw there. So using those old tool marketing mechanisms that we had to learn way back when, that still applies. And as long as we’re using those in our subject line and pre-header, we have a lot better chance of getting an open.  

Rich: That’s great. Are there other things – before we move on – that we should be focusing on when it comes to some of these tactics? And you mentioned the “welcome” message and the pre-header. What other things should we be paying attention to?

Jessica: The big thing I’ll say is just like any channel, email is evolving over time, and there’s been some discussion about the length of an email. And again, this is completely different for a business to business, technology to writer, than it is for the restaurant down the street that has an event going on Tuesday.

So it’s very specific to every market to understand what your audience needs to see or wants to see and what they’ll interact with. But in general, email is not the place to put the whole enchilada. The email is really meant to be sort of a second level of enticement to get them to do something else. And sometimes that is “walk right into my restaurant”, and sometimes that is “click through to buy”. Honestly, some of it is the email is one of a series of emails that is trying to get you to reach back out to me to schedule some sort of an appointment or demo or something like that. “So I’d love to talk to you more about our services and give you some stories of people I’ve helped in the past”, that email needs to be pretty brief, and it needs to probably click through to more information, more social proof, more case studies.

All of that really needs to live on your website. You need to have a brochure or profile built, but it doesn’t all need to go in the email. And one of the mistakes I see people make quite a bit is trying to put every idea into the email, when really each email – just like a social media post – probably needs to stay pretty focused to a primary message and maybe some supporting messages. 

Rich: I have noticed that the length of emails seems to have gone down over time. It feels almost like email and email marketing is more almost about a transition of getting someone out of their inbox and back into your website, more than just sharing a long article with them. Are you seeing similar things in your industry? 

Jessica: It’s an interesting observation because I think that’s true for some industries. I think that the newsletter is still a work horse – big time – for the right industries. And those are largely going to be business to business or somebody where your thought leadership is a huge portion on your brand image. And those people that have long lead cycles – I go back to a technology example – I came from a company that was a service provider, and our sales cycle from when we met somebody to when we were likely to start working with somebody if we were to close that business, was between 12 and 18 months. And you can’t just hit them for 12-18 months, so our newsletter was just a way to stay in front of that person to give them a little bit of free insight in exchange for a little bit of their attention, and to hope that our brand rises to the top when they’re ready to look at or consider different technology options.

So I think the newsletter still carries a lot of weight for the right type of product. I think what we’ve seen go away – and I’m sort of grateful for this myself – is that volume of email where every product thought they needed a newsletter. I love the behind the scenes stories of your employees, but sometimes that doesn’t need to go out to your prospects or your buyers as often as it just needs to be something for your internal company culture.

So I’ll switch examples here and go to a clothing company, let’s say you make your own t-shirts. Some of that is your brand, you can totally put your brand together in your emails. But sending something every month “newsletter-style” just because it’s a newsletter, doesn’t fit as well as sending out promotions when it falls in line with your content calendar, if that makes sense.

Rich: It does. I’m going to totally take center stage here and just kind of pick your brain on this thing, even though I hate the phrase “pick your brain”, I apologize for saying it out loud.

So my day job is for a digital marketing agency, and we do a lot of educational blog posts and those are almost always emailed to our clients. Unless it’s something like we just launched a new website. So if we do something like I did recently about how to land your first podcast guest, now I have for a long time – in part because I see other internet marketers doing this – is I have the email more conversational. Where in the old days, I would have put the entire blog post into that email. If people read it in my email, great, if they read it on my blog, great, as long as they read it

Do you think that I’m making a mistake and I should just be putting all that content into an email and not asking people to leave the email in their inbox to go get that information? Do you have a strong thought either way?

Jessica: So I have kind of a double answer. The first is the easy one which is, as an email marketer I like putting the short version or a snippet of that blog post or research or asset that you’re trying to drive them to. I like putting a little bit of a blurb in there, too, a teaser or maybe a really strong opening paragraph, then saying click to learn more, partially because I like seeing the clicks. So the click is an indicator to me that they engaged with it or read more of it than just the first couple of sentences. And to me, that gives me an indicator. So selfishly, I like doing a little bit of a short link for more process because it helps me track how well my content or my asset is doing with my audience.

The flipside of that, the “right answer” is, what is your goal for your newsletter.

Rich: Well I guess my goal would be that somebody would read that blog post and think this is a company that I want to be working with.

Jessica: Bingo. So here’s the thing that I found out, and I did a similar setup, again I was with a technology company and I had a newsletter and we tested 2 different subject lines and we determined that the open rate of one was better. The click through rate of the other one was better. So I asked people which one won, which one should I mimic going forward. And I had people saying “open rate”, I had people saying “click through rate”. And if somebody says “open rate”, I always ask them why.

Why would open rate be more valuable to me than click throughs to read the rest of the article? And the answer for me was, because I only need them to spend a little time with my brand. What’s on that webpage does not get them closer to a sale with me. I want them to read the article and remember that I’m a thought leader in the space, and I want my brand to be in front of them for a little while. So for me, something that has a higher open rate actually means that I spent a little more time with those people. And it’s my hypothesis that long term, the people that open consistently are going to be of more value to me than just getting a high click through rate from a smaller percentage of people.

So again, it’s what your goals are. If you have products listed on your website, if you have consultations or something listed on your website and you want them to spend time on the site as part of cultivating or nurturing that relationship, then the click is where it’s at. And there may be cases where as a new subscriber where you’re welcoming them, and you really want that click through because the click through is kind of how they get that next ask. And in that case, you’re going to measure against clicks.

But for the most part, when you’re business to business, your newsletter is about being in front of people on a consistent basis. Almost staying top of mind the way old school media does. SO I would argue that the benefit to you is to have a well-read summary in your email, and then let people click through if they want more.

Rich: That’s a great answer, and it does make me start to wonder if even if I don’t move all of my emails to long form, at least experiment with some of them and see what happens.

Jessica: That’s exactly right. And like I said, the email industry sort of has a running joke that every answer to every question is, “it depends”. And I’m trying really hard not to use that, but it does. It depends on your audience, it depends on how you cultivated that audience, how people got on your list, what the expectations are. It definitely depends on your product and that lifecycle or sales cycle.

And the right answer is, you’ve got to test it. You’ve got to figure out what time of day and week works best for your audience, what subject lines or subject line mechanisms or motivators work the best for your audience. In this case, test whether short or long form gets better engagement. 

Rich: Absolutely. And I’m also kind of curious – because the other brand is the Agents Of Change brand – and when we go live with yours there will be a nice picture of you and your best quote from the day, and then I’ll talk about what amazing things I learned from you, and then it’s click here to learn or click here to listen.

And now I’m wondering, we do a full transcript on the show, I may start experimenting with here is her best line for sure, but here is the full transcript – or maybe the first half – and then see what response we get from that as well.  

Jessica: I think that’s an excellent test, especially because though video is becoming a more assumed part of most marketing programs and most consumers – or in some cases business to business prospect – for me, watching video used to be time consuming, and now it’s so the natural part of…leaving a podcast on is completely normal to me.

So that becomes a lot more accepted and a lot more accessed. But at the same time, I still have those days where I’d rather skim so I can skip to the part there may be pertinent to me. And I found that a lot of people do transcripts – especially podcasts or webinars – that we do.

Rich: Absolutely. So you had mentioned earlier in the pre-header section that you liked to see the pre-header above the image. So one question I was going to ask you today is, should we go plain text or HTML? Now I run a digital agency where we’re all about design, so I’ve always done this. But I notice when I look at some of the leaders in the internet marketing space, they’ve almost all moved to a plain text email that comes across as if they’re writing directly to you with your name on it, and it’s a one on one conversation. When it comes to brands, do you think that works for them, too, or is that something that really should be left to the solopreneur information peddling people out there?

Jessica: I love “information peddling”, that’s good. You know, there’s a little bit of a dichotomy there, too. It doesn’t seem as authentic if let’s say Jessica at Hallmark emailed you. Did she really? Of course she didn’t. So there’s an authenticity gap between you doing it because you are the face of Agents of Change, or in technology feeling like the inventor of a certain app or piece of technology is really emailing you. I don’t believe they emailed me either, but at least I know them as the figurehead of that company.

I actually strongly believe that emails should probably come from brands as long as you’re a more scalable brand. We have a great example here in Kansas City of a coffee roaster, and about once a month their CEO writes an almost Christmas-style letter, and it is long. It’s all words and it’s got his signature at the bottom as if he actually sat down and wrote you a letter. And for whatever reason, it goes gangbusters for them, because people know him as the figurehead of the company, and even his emails still look like it came from the coffee brand. It’s from the Roasterie brand, it’s got the banded header at the top, very simple body, and then a little bit of branding at the bottom.

So I think it depends on what your product is, but the one to one that you’re seeing is either really one to one – which would be great – or it’s a mimicked one to one. And that’s where marketing automation has become really popular. Especially in technology sales, you totally hit that nail on the head. 

In technology sales, they have an entire marketing force to support their sales force that is making emails that actually look like Bob sat down at the computer and typed an email to Jessica. Of course in that case Bob is not, but the authenticity and feasibility of that is actually extremely high. Bob really could have sat down to write the email, but in order to save time and be able to track the results of that email, he used a marketing automation platform instead.

So I think you kind of just have to balance that. If you have a one to one relationship with somebody, especially a sales relationship – and this is pertinent so that if I pick up the phone and call you, you know who I am – then absolutely use that. Because that is the piece of the brand that your prospect or customer knows.

On the flipside, if what you’re selling is more like shoes or t-shirts or a restaurant, unless the chef or the well-known persona for that restaurant is really involved in their marketing, I would say let the brand do the marketing and go ahead and use some of that great design that you have the capabilities to use.

I’m one to say the difference between the design and the plain text, and the truth is they’re totally different mechanisms. If you’re going to do a promotional email saying that you can get $3.00 off of a shipment, then just go with a great looking branded email that uses all of those visual elements that we know help drive response rates. Don’t use just the text only, because it might look like it’s more personal, but you sort of have to fight that authenticity battle.

Rich: Good stuff. Excellent. So this has been a lot of good information, and we only got to a few of my questions. But I don’t want to keep you all day. I know that there’s more information online, where can we learn more about you online, Jessica.

Jessica: Absolutely and there are so many good resources in general. I have plenty that I follow including Litmus. They are one of the big content creators in the email marketing space on how to design and make great emails. 

But me, personally, I put out some fun stuff on the Barkley Free Knowledge. We call it “free knowledge”, because of course, it’s free. And I write about once a month for them. There’s lots of other goodies in there for marketing and the trends that we see in content marketing and things like that, as well. So that is one you can check out at barkleyus.com, and click on that “free knowledge” button right at the top.  

Rich: Excellent. Jessica, thank you so much for stopping by today.

Jessica: Excellent. Thanks for having me, Rich.

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