The New Rules of Email Marketing

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By now you know the importance of an email list for your business. But are you using those email addresses wisely and strategically, or are you just bombarding your clients – and prospective clients – with emails that will eventually cause them to remove themselves from your mailing list?

One of the biggest mistakes businesses make is using their emails to actually try to sell to their audience. The key is to use the emails to direct them to other platforms that excel in selling – like your website.  But avoiding a few common mistakes, you can start sending out the kinds of emails that get you more clicks, longer engagement, and make your audience want to read the next one, and the next one, and the next one.







Rich: Matthew Montoya of Constant Contact has crisscrossed the country, hitting 46 states, helping in person over 9,000 small businesses to better understand how email marketing can affect growth and impact your bottom line. In addition he’s taught over 11,000 small businesses and non-profits via webinars, and holds nearly constant training and support for Constant Contact’s extensive and exclusive group of reseller partners.

In his 16 years in marketing he’s worked on nearly every kind of marketing vehicle from print, broadcast, social, digital, web, and email. He’s seen and had a roll in them all. His extensive background has helped thousands of organizations rethink their email marketing strategy to meet the expectations of today’s jaded email subscriber. Matthew, welcome to the show.

Matthew: Thanks Rich, glad to be here.

Rich: I’m glad to reconnect with you, because of course you were one of our star presenters at the Agents of Change Conference.

Matthew: That was such a good time, though. Such an excellent experience. Thank you so much for having me.

Rich: So as I mentioned in the intro, you’ve been involved with a lot of different elements of marketing. Why are you so bullish on email?

Matthew: You now, there are several reasons for that. I’ll give you a little backstory, going back about 10 years ago now I was in print and I could see the writing on the wall. And as I re-thought my career the one thing I realized was unless they’re something completely revolutionary, email is not going away. In fact, I often ask these groups when I speak to them what’s the one app they check every day. Of course someone will yell out Snapchat or something else, but of course it’s email. We don’t think of it as an app, we don’t think of it in the same way that we think of those other social media-style apps, but it’s the one thing we check constantly. Any time we get a notification we’re always checking it, email is a really powerful tool.

The problem is – and I like the fact that you said “jaded” – is that people have gotten savvy enough that we can’t get away with the kind of typical old school email marketing, a laundry list of different products and services, different kinds of content that makes an email really long. And I think that’s where that kind of negative feeling around email marketing comes from is that there’s just been years and years of bad email marketing so we can’t do that anymore.

Rich: Well that kind of leads into my next question, because I hear a lot of small businesses that I talk to focus primarily on social media. They’re talking about Facebook, and they’re talking about Snapchat, and Instagram, and they don’t give a whole lot of thought to email marketing as part of their digital marketing strategy. What would you say to these people?

Matthew: Well you know I believe in a whole ecosystem, I mean there’s absolutely a role for small business to use social media. But a couple of things I would encourage a small business to think about, the first one is ownership. When it comes to social media those followers and those people that like your organization or connect to you through social media, you don’t actually per se “own” them. If there’s any kind of change in the software or terms of service, you could lose out in those contacts or that experience.

The second thing I’d encourage a small business to think about when it comes to social media versus email marketing, is intent. When you think about it, a small business collecting email addresses, that is a very deep potential relationship. Most of those email addresses were collected at trade shows, on a conference call, in a one-on-one meeting. Those email addresses were collected by small businesses, those are people that are already either sold on the small business or are very interested in what the small business has to offer. So when small business collects those email addresses, there’s a lot of potential revenue with that experience. And again, you own those email addresses from then on out. 

And then lastly, email marketing when you think about the differences between social media and email marketing, a lot of people are unaware – and I think this is probably something you preach pretty regularly – social media done bad, on the cheap, and without some experience, doesn’t necessarily produce results. So I think all of those three things together, absolutely email has a role to play in social media, and social media has a role to play in email. But to use one without using the other can ultimately hurt a small business’s bottom line.

Rich: I completely agree, obviously, I’m a huge fan of email marketing. One of the things I tell people – even while they listen to this podcast – they might be missing dozens of Facebook posts and hundreds – if not thousands – of tweets, and they’ll never see them again. But any email that is delivered into their inbox is still going to be there waiting for them. It’s almost unavoidable.

So to get access to what I call “the most valuable piece of real estate on the internet” makes a lot of sense, and that’s what email marketing delivers.

Matthew: Absolutely. And you know driving people to the pages that you want to drive them to is obviously critical in that most important real estate, but of course with email marketing you get to track that behavior. And so if I send out an email and I notice that out of 1,000 people 200 click on a particular product or service that I’m offering, I now have a hit list for follow up emails. Doing that kind of analytics and behavioral response in social media, it’s pretty hard.

Rich: Yeah, absolutely. Now we’ve been preaching the importance of email marketing, the critical nature in your overall digital marketing, on this show for a while. For the people who have been listening – and they know that this is important to them – I’m sure they’re interested in getting more subscribers. What are some of the strategies and tactics that you’ve seen work to build your subscriber base?

Matthew: Well first and foremost I’m going to go a little old school here, it comes from the owner, the operator, the head of the organization, believing in collecting email addresses enough that they’re doing it themselves. Then it goes down a level into the frontline staff to make sure the frontline staff are asking for the email addresses and explaining to people what they’ll receive in the email. But you know, asking for it. I find that basic step is the one thing a lot of organizations have trouble embracing.

If it’s only the staff that’s behind this or are being encouraged to do it, it’s going to eventually fall by the wayside. They’re taking orders, they’re on the phone, they’re doing their job, and ultimately asking for email addresses falls by the wayside. So it really starts with the owner believing that those email addresses contain a large potential revenue stream that will not be used or accessed if you don’t do email marketing. So it starts at the top.

Other ways to grow their subscription list that works well, again kind of basic simple philosophy here, it’s not earth shattering. Make sure you’re soliciting for email addresses on your website, on your blog, and through your social media channels. Make sure that you’re getting that solicitation out there where those consumers – or potential consumers – will be visiting.

And then also think about how you’re accessing one-on-one collateral-type experiences. So invoices, receipts, flyers, handouts, window decals, billboards, print buys, radio buys, television buys, all of those experiences. How are you soliciting for email addresses in those kind of experiences? Because so many people are going to interact with you in that kind of content, so make sure that we use something like a “text to join” or similar feature that can solicit for email addresses there.

Rich: Now on that first item that you mentioned, basically the owner and the staff talking to people. So what you’re saying if I’m understanding you correctly is, “I’m on the phone with a prospect or someone who is calling in, and as part of my “script” – so to speak – I’m going to say, “Hey, do you mind if we add you to our email list? We’ll be sending out bi-weekly emails that are going to help you grow your business, generate more leads, save money on whatever we might be selling.” You’re just saying that should be part of the conversation we’re having with just about anyone we get in front of or on a call.

Matthew: Absolutely. If the top of the chain doesn’t believe in getting those email addresses, no one else will, and it needs to be part of the script. Now that can be on the phone but that can also be for retail like when somebody comes in, “Hey, would you like to be a part of our email club?”, and offering the laundry list of things they might receive in that email. That’s Email Solicitation 101.

Rich: Alright. Now we’re all overwhelmed and inundated with emails these days. I was just on Facebook complaining about this earlier today. How can we make our emails stand out, get noticed, and get opened? What are some of the things that you’ve seen people do that really had a big impact on open rates?

Matthew: That’s actually a somewhat complicated question to answer, because one thing I want to make clear to all the listeners – and I know that they know this – is each situation, each small business, each organization is different. But high level some generalization. One is to make sure that the list that they are using is as segmented as possible. Making sure that you’re putting these contacts into various buckets that makes sense for the business.

So maybe that’s separating them by the different kind of products you offer, for different kinds of services you offer, break them up into customer and non-customer lead, etc. So making sure that you segment those out and then build content around those segments, making sure that the content that you’re sending out is as relevant to that particular audience as possible.

I’m going to go back to 10 years ago when we were sending emails out. Back in the late 2010’s and earlier you could send out a laundry list email with 3-4 different subject matters that might appeal to 3-4 different segments. Now especially because of smartphone usage, people are only spending seconds in an email, we want to make sure that content is as relevant as we possibly can make it so that it will be received well. And the philosophy behind that is not only to get them to read the email and act on it, but also to read the next email, and the next email, and the next email. Because if we don’t provide relevant content to that particular smaller segmented group, odds are they’re going to assume that every email is irrelevant and they’re going to stop paying attention.

The last example I’ll give you is you kind of have to watch how you sell in an email. A lot of small businesses instincts are to do nothing but promotion in an email. And what you want to do is you want to mix that content occasionally, you want to mix that content with something that’s educational or informational, or going to showcase the business in some other light other than just trying to sell you. And the reason for that is – except in rare circumstances – not everybody wants to buy right now, they’re not in the position in the sales cycle to buy right now. So you want to retain that relationship until the moment when they’re ready to purchase/attend/buy/do whatever you’re trying to get them to do. And if all you do is promote all the time through email, you can be alienating that group of people.

Rich: And like you said earlier, I think it really does depend. When you’re talking about somebody like me who’s got a digital agency, people aren’t buying websites or even social media strategies or email marketing strategies every day, so it’s more about education. When you get something like Groupon, you don’t really care about anything but the deal. So I think it really does – like you say – depend on the type of company you are and what people are expecting from your emails in the first place.

Matthew: Absolutely.

Rich: So you mentioned segmenting lists, and I wanted to get to this anyways. I love the idea of segmenting lists, but if I’m being honest with you, many times I’ve tried to segment my list and then all the smaller groups just gather dust and I never use them. The only time I’ve ever had any success with both flyte and the Agents of Change when it comes to email segmentation, is when I was able to segment out a local group. Because I figured those were the only people who were interested on events that we were putting on here at flyte.

With small businesses there’s only so much content we’re going to create, and sometimes segmentation feels overwhelming. What are some basic tips that are really going to make a difference when it comes to segmenting our lists, and how do we segment the list? Do we ask people to join extra lists, or do you have some ideas around that as well?

Matthew: There’s a couple of ways to approach that. One is I want to encourage everyone that gets that overwhelmed feeling, it doesn’t have to be a completely different email for every segment. You can reuse parts of that email for different segments, even if it’s just your introduction. Treating these groups differently is going to have some impact.

I’ll give you a real world example form my life. About 10 years ago I was working for a nonprofit, and when I first started there they were sending emails out to members and non-members and even vendors, they were sending one email out to all of them. And I realized we don’t want to talk to members in the same verbiage, in the same way, that we would talk to the non-members. And of course we’d want to change up some of the content but it was really just the way we were talking to them, we wouldn’t want to talk to a non-member in the same way we talk to a member because it’s making the assumption they’re already a member.  We want to make them feel a little excluded so that they’ll buy the membership and join. So it doesn’t have to be completely different content.

Now to go into the second question you asked, which is more about how you do it. One, don’t feel overwhelmed that you have to break it into these extremely tiny super sub-segments. That’s optimal, but ultimately you’re probably going to need to hire a professional to help you do that because that is a lot of data management. If you’re doing it yourself start with those big buckets first, “customer” and “non-customer”, “this product affinity”and “that product affinity”, “this location” and “that location”. Start big, at least you’ll be receiving better results just by doing that. 

Now to specifically answer the question about how, one of the easiest ways a small business can start segmenting – there’s actually two ways – once is  scheduling some time with you and your staff and making your list and making either assumptions or knowledgable choices about who belongs where, and breaking them up that way.

The second easy way to segment is by creating an email that’s designed to help you segment. Meaning you put out an email with 3 different products or services, or 3 different avenues of information. By monitoring what people click on, and moving those people through your reports into a segmented list, it’s not perfect but odds are by their clicking on that particular link in the email they’re actually telling you something about what they’re interested in, or where they live, or what they look like.

In the same vein sometimes some small businesses can be really overt with that. Putting in a series of links with your emails that literally ask, “What zip code are you living in? What product are you most interested in? What describes you as X?” And when they click on the button or link that describes them, you now have that information with nothing more than them just clicking on a link.

Rich: Ok that’s definitely helpful, I’m glad that those tools exist. Now I’ve heard you say that email marketing is not the message, it’s an ad for the message.  What do you mean by that?

Matthew: If there’s one theme for this podcast today, it’s “Matt is older than he’d like to be.” But I’m going to go back a little bit and talk about behavior that small business nonprofits used to do, which is the laundry list email, one size fits all, the thing would be 10 scrolls. You can’t do that anymore. And the primary driver for that is smartphones. The average subscriber is going to spend anywhere from about 15-30 seconds on a PC or a Mac or a tablet reading an email that becomes about 5-10 seconds on a smartphone.

So what I encourage small businesses and nonprofits to do  when I’m either training in person, speaking to a group, or doing a webinar, is to make sure they’re always linking. Make sure that you give folks just a taste, just enough information to pique their interest and get them to click and go to read more, to learn more, to watch that video, to interact on social media. And there’s a couple reasons why you want to do that.

One is again, most software packages are going to track the behavior, they’re going to track the click, so you learn something about that subscriber. Two, behaviorally, somebody when they click on a link to read more or watch that video or do whatever, they’re making a time commitment. They want to learn more so that 5 seconds might become 45 seconds or a minute.

And in that process as you’re motivating them and they’re reading the rest of the content on the website or the blog or on social media or watching that video, now you’re selling them. Somebody’s not going to be in the metal headspace to buy, or attend, or donate, or whatever you’re trying to do in the email, They’re just not there, it’s not a transactional mindset that they’re in. But when you get them to click, now the time is slowing down, now you have more chances to convince them to do what it is you want them to do.

And so when I say that the email is not the message it’s an ad for the message, having that mindset of knowing that people are just going to be spending a scant second in this email, and we want them to go and actually be convinced to buy somewhere else is key to being successful today.   

Rich: I would also wonder as you’re talking about the idea that once we get them to our website we can also then start different remarketing packages, retargeting, and we can also get them to engage with our content through social shares as well. And maybe those things are all doable in email, but it seems like they’re more normally done on a website.

Matthew: Absolutely. And it’s mainly just kind of small businesses and nonprofits – even medium sized organizations – really just need to realize that the purpose of the email is not necessarily to sell or motivate, it’s really to get them to the platforms that are good at that. 

Rich: Absolutely. Now we’ve kindo of touched on this already, but once we’ve gotten those emails opened, how do we get people to take action? Are there some things that we should keep in mind as we try and move them from inbox to landing page, things that we can do within that email itself?  

Matthew: Yeah sure, there’s a couple things. One is – I’m going to call back to my days in the newspaper industry – be aware of the scroll line. So in newspapers the term is “above the fold”, we want to have that same philosophy in an email.  Make sure that what the main purpose of the email is, the reason you’re sending it out, is high up in the scroll line. So before somebody scrolls as they’re first glancing at that email, they need to within a split second understand what the call to action is.

The second thing is to make sure you’re using images and text wisely in the email. And that’s actually one pitfall I see a lot of small businesses and nonprofits do.  They either go to one end of the spectrum or the other. So starting with the images, a lot of organizations will rely too much on imagery. And the danger there of making an email that’s mostly image or all image, is that images are still often blocked. I’d be willing to bet your listeners have gotten an email at some point in their life where they have to download the images. Well that happens roughly 40% of the time. So relying solely on mostly images, you might be providing people mostly or all of nothing, just a white screen.

The second thing to actually balance it out, you want to have some text supporting that image and that call to action. The other example and the other end of the spectrum is organizations that bury the lead, they make the image really tiny. The purpose of the image is to convey to the reader in a split second what the content is about. So making sure that the image is directly related to the content, making sure that the content and text is either wrapping around the image or very closely adjoined to the image is key to getting behavior.

The last thing I’d suggest for best practice in getting them to that landing page to that website is making sure you’re utilizing both images and buttons in your email to cause the click. So what a lot of organizations unfortunately still do is they use hyperlinks in their email, and hyperlinks are awfully hard  to click on on a smartphone, especially if your email is riddled with them.

So what I encourage small businesses  and nonprofits to do is make sure that their images are always clickable to the page that’s reflected or resident to the content, and to use things like buttons where are usually literally buttons in your email that people can similarly click on and go to that site, go to that landing page, go to watch that video. Those things make it really easy for somebody to;  1) understand the content, 2) understand the relevance to them, and 3) take action very quickly, is key.

Rich: So as we’re on the cusp of 2017/2018 – depending on when people listen to this – what are some of the trends that have emerged in email marketing, or what do you see as the next big thing in email marketing?

Matthew: That’s actually a very easy one for me to explain. Automation.

Rich: Ok, go into a little more detail.

Matthew: So automation when it comes to email marketing is several layers to this. One is automating the segmentation of automatically moving the contact that take some behavioral movement in the email – clicking on a lik or watching a video – and automatically relaying that into a brand new list. That’s the first level, kind of high level of automation.

The next layer would be because somebody clicks on something they’re going to receive – a follow up email or a series of emails – because they showed affinity to that particular product or service.

The next layer of automation would be based on demographic information or behavioral information. So perhaps let’s say one person who has opened emails regularly would get one version of the email, somebody who is a casual subscriber who doesn’t open every email or doesn’t open email after x amount of time would get a different kind of email.

Taking that a bit further, maybe a retargeting or re-engagement campaign where the software looks at people that have yet to open or don’t open regularly, and sends a unique email to them. And so what we’re seeing now and what we’re going to see definitely in 2018 is much more automation. All those things I just described and more.

Rich: Fantastic. Now I know that people are going to want to learn a little bit more about you and Constant Contact, Matthew where can we send them?

Matthew: So if you want to learn about me, I’ll be selfish for a second and you can connect to me on Twitter @MatthewMontoya_. But for Constant Contact, the best place, I’ll actually give you two places to go. If you’re interested in having a free trial in Constant Contact, We have a 90 day free trial, you can actually build some emails and see some of this technology that I’m talking about. Another place if you want to learn more is There we write daily articles about email marketing best practices, social media marketing best practices, and beyond. But we also give webinars – many of them I host – we have free training all over the country for you to attend, so there’s a lot of ways that people can learn more about this.

Rich: Awesome, and we’ll of course have those in the show notes. Matthew I want to thank you so much for coming by today and sharing your expertise with us.

Matthew: My absolute pleasure Rich, thanks for having me.


Show Notes:

Matthew Montoya loves helping businesses succeed with email marketing. As a member of Constant Contact he shares his expertise through blogs, webinars, and speaking engagements. Feel free to reach out to him on Twitter and tell him you heard him on the Agents of Change podcast!

Rich Brooks is the President of flyte new media, a web design & digital marketing agency in Portland, Maine. He knows a thing or two about helping businesses grow by reaching their ideal customers, and to prove that, he puts on a yearly conference to inspire small businesses to achieve big success. You can also head on over to Twitter to check him out, and he just added “author” to his resume with his brand new book!