Ask Amanda About Marketing – Episode 29: How to Confidently Click “Send” (And Have People to Send To)

When you’re drafting emails for your brand’s email list, do you end up having a bit of a Tom-Hanks-style writer’s block?

, Ask Amanda About Marketing – Episode 29: How to Confidently Click “Send” (And Have People to Send To)

I spoke with digital marketing guru Wendy Maynard about her email marketing tips for beginners and pros alike. Wendy explains:

  • Why email marketing is important
  • How to focus on quality rather than quantity
  • Everything you need for a successful email marketing strategy
  • How you can improve even the most impressive email strategy


Mentioned/Related Links:

, Ask Amanda About Marketing – Episode 29: How to Confidently Click “Send” (And Have People to Send To)

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Full Transcript:

Amanda Milligan: Welcome to Ask Amanda About Marketing, a podcast in which I, Amanda, or occasionally a special guest, answers your questions about inbound marketing. Straightforward, right? If you want to submit a question, e-mail me at [email protected]. I’d love to hear from you. Let’s get right to it.


This week. I’m joined by Wendy Maynard, who has been in marketing strategy and business development for about 20 years now. Welcome to the show, Wendy!


Wendy Maynard: Thank you so much. I almost hate that announcement because I feel like it always dates me, it seems like such a long time.


AM: Haha yeah, but it’s such an impressive stat. I mean, think about marketing 20 years ago and how it compares [to today].


WM: Yeah. Yeah. It’s been an interesting journey for sure. When I first started, most companies were just getting their first website up. I had written a little history of all the things that were happening when I kind of first started. And you know, there was no Facebook. There was no Twitter. There was no Instagram. There were none of the social media sites that there are [today]. At the very beginning, you even had to, you know, go and take a break to get your cup of tea while your next page loads, because there was no high-speed internet, right?


AM: I remember the dial-up days. It’s dark days. That’s great. So just to kick things off, would you mind giving a little bit of the background of your career? What have you been working on?


WM: Yeah, absolutely. So currently, I have a consulting and coaching business and you can find out everything about me at I kicked that off, oh it’s been almost a year now. So the end of May last year is when I really started that, and I have two feisty young boys. I have a nine-year-old and a two-year-old, and that was part of the reason why I decided to make the switch. But before that, for almost 18 years, I had co-owned and had co-founded a marketing firm. It’s based in Portland, Oregon and I sold my half of it. Like I said, just to stop traveling, be with my little guys a little bit more. That firm is doing great, it’s continuing to grow, but I really just wanted to continue to work closely with CEOs, business owners, and entrepreneurs and scale their businesses. I don’t have to travel as much. I work virtually like many of us, working from home gives me a lot more flexibility and time to be a mom which is important as well.


AM: So you’re on the show today to talk about email marketing, which we haven’t really discussed in length on the podcast so far. So I’m really excited about this. And I want to start just with some top-level questions and you can answer them. These are usually pretty big questions. You can answer them however you think makes the most sense.  


WM: Perfect.


AM: Why is email marketing, in general, an important part of a marketing strategy?


WM: Yeah, so I find that in certain industries, this is really underutilized and so it depends on the industry that you’re talking about. However, that said, it doesn’t really matter what type of business you own. Email marketing is super powerful. There are studies from the Direct Marketing Association, for example, [which] states that your return on investment—so for every dollar that you spend on email marketing—your return is $38, which is insane.


AM: Wow.


WM: Yeah, it’s insane. And some studies I have read it actually puts it up a little over $40 and it depends on you know, what you go with. I go with a DMA study just because you know, they’re a pretty good organization and I trust their studies; but it is crazy. Nothing else gives you that kind of ROI. No other social media. No other type of advertising. No other type of, you know—people tout YouTube channels and Instagram or whatever it is, like whatever the latest and greatest is. I always look at those channels as opportunities to grow brand awareness and drive traffic to your site. But ultimately and again, I don’t care what industry you’re in because I have worked with tons of businesses and tons of different industries—getting an email list up and running and then nurturing that list and having strategies to convert those folks into customers, the return on your time and dollars, there’s nothing that matches it.


AM: That’s a pretty incredible ROI right there and yeah, the strategy will vary based on what industry you are in, but say someone is listening right now, and they are thinking, “Okay, I don’t have an email strategy.” What is the first thing you need to take into consideration if this is something you want to try out?


WM: So the first thing to take into consideration is getting an email service provider. So that’s the first step, and I have two that i work with a lot. There’s tons out there. Personally, I use ConvertKit. I feel like that is a really great tool if you are in an industry where you really wanna send frequent emails. It’s text-based, which is actually an advantage because you’ll get higher open rates.


That said I do have certain clients that I work with MailChimp. MailChimp allows you to have more graphics in there and they’re free to get started, which a lot of people like. I think you can go up to a couple thousand. So, those are two good places to start. Now, that said, I’m not dissing any of the others. There’s tons of email service providers out there, but your first step is really to get an email service provider.

Then, the next step is to really make sureand I always mention this, I feel like it’s said so much that people overlook it. Yet, I’ve worked with clients and there’s still not as much clarity as they can get on this. I look at it as an evolving process instead of a static process.


But, the key is really understanding who your ideal client is, and again, I feel like people’s eyes are now glazing over because they hear this so much and yet, as I said, I work with client after client and there’s still so much work to be done around that. The reason that you want to get so much clarity on your ideal client is that when you do that, all your marketing messages become so much easier when you truly understand their pains and outcomes that you’re delivering to solve their pains. All of your email content and driving them into the solution that you provide, which essentially is when they become a buyer, all of that becomes so much easier. So that’s reallythose are really the first two foundational steps.


AM: Yeah, that makes total sense. It sounds like you can almost—when you’re building out an editorial calendar, hopefully, based on the same thing you’re talking about which is understanding your audience or your clients and the questions they have and those points you mentioned. You know, not just answering those with the content you’re creating, but also with how you’re going to reach out to them and get their attention and bring them back to the site. So that’s a great tip.


WM: Exactly. Let me ask you something. Do you know which industries most of your listeners are in?


AM: I do not. See, you know, I wish I had that information.


WM: Okay, everyone, listen send your industries into Amanda so she knows better [laughs].


AM: [laughs] Yes, please do. I appreciate that very much.


WM: What I was going to say, so depending on the industry, the next thing you really want to do is start thinking about capturing folks and getting them on your list. And the best way to do that is to offer some sort of incentive for them to give you their name and email and so on, you don’t really need to get complicated. First name is perfect. First name and email is enough. You don’t want to have complicated forms. Your email service provider will have a little bit of code that you can install on your website and if you’re not tech savvy or whoever you work with can help you do this, but you have forms on your website and keep places and then you want to offer your ideal client something that is really juicy to them. And in some industries, they call it a lead magnet and in other industries, it’s a whitepaper.


There’s all kinds of different things that you can offer, but this is—and this is really important—whatever is that opt-in incentive, keep it super focused so it should really just solve one small thing. And this is a place where I see people getting into trouble a lot. They try to be too broad and so you really want to think about your ideal client’s pain points and solve one thing. So it should be actionable and it should be fairly simple.


Let me give an example: If you were say, a person who helps folks get their lives organized and become more productive, right? There’s tons of things you could offer them. But if you, say, offer them something like “how to organize your whole house,” and that is the free thing that you are offering, they probably aren’t going to succeed because that’s overwhelming and they are not in that habit. So, you want to give them one simple thing that they can get a win with and that might be, you know, 10 minutes every day “how to have a clutter-free desk” or in, you know, just a few minutes a day “how to keep your kid’s toy box organized.” Whatever it is and whoever your target audience is, make it super simple.


And then the other thing is ideally you want this to be a stepping stone towards whatever offer you’re going to make them. So, it should be a tiny piece of that much bigger picture. Whatever that is, whether it’s a service or a program or a product move them along a pathway where the thing that you’re offering in exchange for their name and email is a and z is the offer that they’re going to buy from you.


AM: I love those tips, especially keeping it simple because I do think that a lot of people’s intuition would be okay. We need to include as many tips as possible because we want to appeal to literally everybody, not realizing that it’s easy to overwhelm people and they’re not going to want to filter through a million, you know, a million paragraphs or you know, this huge white paper to find something that’s going to be valuable for them. So, I think that’s a really great point.


So you’re talking about putting these really simple forms onto your site. Where does it make sense to put those forms? You know, I’ve seen many different versions of this, whether it’s at the end of blog posts, if it’s a pop-up menu that opens when you scroll a certain amount of the way down—what have you seen to be the most successful?


WM: Well again, it depends on the industry, but the places that I really like to see them is at least one place on your homepage up near the top so that it’s highly visible. Now that said, you can have it in a bunch of places on your homepage. You can actually have multiple lead magnets if you’re targeting people going down different paths, so to speak, so you would have different offers. But you can have it in different places on your homepage. That’s a key piece of real estate. And then I also recommend that you at least have a link to something on your About page because your About page is the second most visited page on your website. People are always going to [your] about page to learn more about you.


So those are two key pieces of real estate. The other places that you can have them are on your blog post as you mentioned. Now, these get a little bit trickier because you really want to have the opt-in incentive that you’re offering to be related to your blog post. So it has to be a little bit more tailored. It should really be a piece that’s related to the blog that they just read and it should be giving them a little bit more. It’s typically called a content upgrade and you can have a form in the middle of your blog post and at the end and those are there’s a good places to have them.


Let’s say it is a blog post that is talking about some element of, let’s just say, search engine optimization and you are an SEO firm. You talk about a specific aspect of that and then maybe your opt-in incentive—your content upgrade—is just a quick checklist that someone can walk through to help them. So it should be something that’s actionable, something they consume quickly, and something that is a value add to what they just read. This will give you the highest conversions. The other option is actually to have an opt-in form on the side of your blog post. And in that case, it can be one of the lead, you know, one of the lead magnets or the opt-in incentives that’s a little bit broader. So those are some options of places to put them that convert really well.


AM: And setting it up that way, I saw on your personal blog that you had written about the importance of quality over quantity when it comes to building out these email lists. Can you speak any more about that and how does this set up kind of lend itself to creating that kind of a balance?


WM: Yeah. So let’s say so in relation to the blog post you mean?


AM: Or just in general, like how are you best setting up a structure in which you’re going to get better quality people joining your list rather than just trying to like, ramp up the number of people right?


WM: Right, thank you. So this comes back to really knowing your ideal clients and a lot of people think about quantity first. So, I want to have a hundred thousand people on my email list or—you get that same thing with traffic. If my numbers are increasing that I’m doing well, like I just want to get more and more and more traffic. Well, none of that matters if it’s not qualified people that are going to be a great lead for you and convert into your ideal customer, right?


Because what we all want is we want to work with customers who are ideal to us. They are people and businesses that we love and that I think is what is so essential. That’s why I always talk about that foundational piece first. Who do you want to work with? Who can you serve the best and what do they need? And that is why it’s so important to do that exercise first.


Do you usually include links, Amanda? I do have a blog post that I can send a link to the has information about your ideal client if that’s helpful.


AM: Yeah. Absolutely.


WM: Okay, so I’ll send you a link to that in case people want to read it. But the important thing is to really think about that person and I always like to think of it as a person not a group of people. Create a persona and what does that person need most from you. And then create a really quality opt-in incentive for them that is going to help them solve that one thing, give them a quick win. And then you’re going to move them along the stepping stone to that offer. When you work with them, you want to love them because nobody have time for a P.I.T.A. client, and that’s a pain in the you-know-what (laughs). Life’s too short to do that, so make sure you’re attracting the right people into your funnels and then you and your team are going to be much happier.


AM: So, say the listeners are like, okay. I have my email form sign up on my site. I have a vague idea hopefully of the kind of content I want to send to my list. What about the actual email itself? You were talking earlier about the difference between text-only and images, there are a variety of different ways to set up these emails, there’s newsletter format. There’s really quick blurbs linking to a resource post. How do you decide what those emails are going to look like? And how do you optimize them for success?


WM: Right gosh, that is a huge question and a lot of people get stuck. So what do I write to my subscribers? So again, it depends on what industry you’re in but I have a lot of clients who are bigger companies—B2B. They do really well with just once a month. I don’t recommend going less than that. That said, there are other clients who are emailing their list once a week, twice a week. Some people even do it daily. So there’s no right or wrong. It really just depends. I guess, the only wrong is I would say don’t go less than once a month because you need to stay in front of your people’s radar, right? You need to stay on the radar, but other than that, it’s going to depend on your industry and your audience.


In terms of content. This is where it gets tricky, right? So there’s a whole lot of different things you can write about and actually, I have another blog post that I wrote and I think it has 25 different ideas for things to list to include in your content and I’m happy to send you that post to if you want to link to it. One of the easiest ways to start out is if you’re writing blog posts anyway, you can give a little teaser and then link to your latest blog post. So that’s the easiest way to start and I do have a lot of clients who start there and have success. As you get more adept and comfortable writing to your audience, you can start creating—it’s almost mini blog posts that are separate from your actual blog if you want to think about it that way.


I also like to think about what are you going to include as a call to action. And so if you’re promoting a specific service or product or program, is there something that is going to educate and get your audience excited about becoming a little bit closer to becoming a buyer. And so when you think of your content that way that can be really helpful.


AM: Right, you’re actually trying to move them closer to making that purchase and that’s a good way to focus the kind of thing you’re going to send out.


WM: Exactly.


AM: I’ve seen I think it’s Brian Dean from Backlinko who does really good versions of what you’re saying where he kind of gives you a story and is even older than ultimately links to a resource. They are so engrossing when you do that when you’re able to really sounds honest and sincere and really hook people, but I can see how that takes a little time to find your voice.


WM: Exactly, yeah, find your voice and don’t be scared to ask people to reply to your emails and get feedback from them. So, that’s actually an incredible way to start understanding your audience as you grow them. You just—at the end—say, “hey reply to this email and tell me how you did…,” whatever your email topic is, or “reply and tell me one of the things that…,” I hate to say, “what are you struggling with?” because that’s become so cliche, but if you can find a different way of saying it like, you know, “what challenges do you face in related to…,” whatever the subject is of the email.


AM: It’s so funny because of all the episodes I’ve done with this podcast, the most common thing that pops up—and so it must be so valuable—is this concept of asking, like actually communicating with your audience, and no matter what we’re talking about that always comes up and it’s people just so rarely do it.


WM: I think that because it feels like we are using a maybe a megaphone, you know, where were shouting out into the ethers. We feel like it’s a one-way channel and it’s really not. So there’s people behind those emails that you’re sending and you can make it, you know, you can make it like a telephone conversation, it doesn’t have to be like a megaphone where it’s one way. It’s actually two ways. It’s just a little bit of a delayed response, right? So, actually ask them and ask them to reply. You’ll be surprised at how many people respond to you once you get that dialogue going and the more you do it, the more comfortable they will be with responding.


The one caveat that I have to say, which I think is really important is when people respond you got to email them back, even if it’s a quick “hey, thank you so much for responding. I love your ideas,” whatever. But if you don’t do that, then they won’t keep emailing you because they’ll get a little bit like well I don’t know what the point of that was.


AM: They’re going to feel like they weren’t listened to at all.


WM: Exactly, yeah.


AM: It’s such a good point because I live in DC and there are some local DC businesses where I’ve been a part of their email list and they were times when they’d say like, “Can we have your feedback? We see you are a customer often and we really want to know.” And that was so striking because I get all kinds of emails, right, of all different brands and to see that and obviously like you’re saying it’s more manageable for smaller companies. But to reply to that and get a response, I can’t even emphasize the value of me being more of a brand advocate that came out of that experience because it’s so rare that you feel that listened to by a company.


WM: Yeah, that’s right. And the other thing that I think is really important is to realize that marketing is a great experiment and you always want to be thinking about what’s working well and what’s working less well. Over time, look at what is getting more responses. Look at what is getting better open rates. And so after you’re in the habit of doing this you’ll find out what your audience is responding to, and I think that that this is really crucial to know that your list of people is unique to you. So you can read all of the information that you want. You can listen to me, listen to anyone. But at the end of the day, you’re going to have a unique list with unique needs and ideas and responses. So make sure that you’re listening to them and looking at what the statistics are telling you so that you can maximize the things that work for them because they’re unique.


AM: Yep. I completely agree. I think there’s some kind of breakdown where it’s like 60% doing the marketing work and 20% strategy and 20% looking back at what you’ve done.


WM: That’s exactly right.


AM: It’s so easy to kind of forget that you can get caught up in the day-to-day doing the work, setting the emails out, composing it. But if you don’t look to see what’s working, you’re kind of just taking a shot in the dark unless you’re refining those those strategies.


WM: And there can be a lot of surprises. I think that you try something else and you get this great open rate and you’re like, what! They responded to this topic, that is really surprising to me.


AM: And that’s the value of experimenting sometimes, like you said, it’s just kind of a process to test things out. Have you seen in your experience something particularly interesting that that performed really? Well that you weren’t expecting?


WM: Yes. Well, it’s been a process. So I was actually thinking about one of my clients and they are actually a commercial HVAC company and they have this really unique philosophy where they believe in doing everything in an environmentally positive way. So they’re moving towards becoming a zero-waste company and they’ve done these incredible things. They also have really amazing ideas around work-life balance and how they treat their employees. So, in a seemingly commodity industry, they’ve done these really remarkable things.


And so we’ve played with their newsletter quite a bit to see what is interesting to their audience. What’s been really interesting is that the tips and information about having a great performing HVAC system—which would seemingly be appropriate for their audience because they do have a lot of property management managers and facility managers on the list—those perform okay, but what we found—and so what we’re now really focusing on—is that there’s actually a lot of their clients who are interested in some of the zero waste activities: how to set up a recycling program in your company, how to know what the different numbers on plastics mean, and how to sort them appropriately. Things that I wouldn’t have initially thought would have performed really well are actually performing really well.


So that’s a that’s an example that stands out to me because it has been it’s been a surprising shift in the content that we have started to focus on and maximize. So that’s an example.


AM: It’s interesting because it is still in line with the brand just like in an unexpected way. You didn’t think that that’s what they would hone in on.


WM: Yeah, and you know, it’s also interesting. You know, I have a lot of different clients that I’ve worked with. That one stands out just because it’s it was an interesting sort of—I wouldn’t say a whole left turn—but you know, we’ve gone on a curve in the road for sure and their subscriber list is you know, it’s definitely getting better and better open rates with some of this—not new—we’ve maximized that content. So that’s been interesting.


AM: Yeah. So it’s a wrap this up. The question I want to ask is if anyone’s listening and they’re thinking “I have a killer email list. I know exactly what I’m doing. There’s no way I could improve.” I mean obviously we know that you can always improve, but what tip would you give to somebody like that to maybe explore how they can continue to optimize their email list? What’s something they can try or something they can check that maybe they haven’t thought of?


WM: Well, I think I think there’s always opportunities to improve because I don’t know anyone who has a hundred percent open rate. So the thing that I would focus on is open rates and really look at the subject line.


So, you can start doing A/B Testing. If someone is amazing at they’re emailing already, I hope they would already be doing this. But you can start testing your subject lines. And if you get really creative with your subject lines, you can improve your open rates. So when you get your emails opened, right, that’s the first huge barrier. So the subject lines are so key. And then the other thing is I would suggest is really working on your calls to action. So, how are you getting people to respond to whatever it is that you’re asking them to do in the email and can you improve that click-through rate? So, you can see that through your email service provider and really that call to action is in some ways like a headline and so it’s a craft, right? Writing amazing headlines and writing amazing calls to action. So can you improve those two things? Can you get your open rates up? Can you get your click-through rates up by improving your headlines and your CTAs.


AM: Awesome, I think that’s a great note to end on something really actionable. This is really valuable for me, and I hope it was valuable for our listeners, and thank you so much for being on the show, Wendy.


WM: My pleasure. Thank you so much for having me.


AM: Thanks again for listening. If you enjoyed this episode, click subscribe. Don’t leave me with the realization that I’m talking to no one and please rate and please review on iTunes so I can keep making this podcast better and your lives easier. Take care.

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