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Tyler Cook Email Marketing Strategies for Better Deliverability with Tyler Cook
The Agents

Are you not getting enough ROI out of your email marketing? If so, is it your deliverability, your open rates, or are people just not taking action? Discover what’s not working and how to fix it with self-proclaimed Email Marketing Nerd Tyler Cook of HyperMedia Marketing, and start generating more business from your email marketing.

Email Marketing Strategies for Better Deliverability Summary

Key Takeaways

  • Understanding DMARC and DKIM: Learn the importance of setting up DMARC and DKIM to improve email deliverability and prevent spoofing.
  • Engagement is Key: Discover how engagement metrics, like replies, impact your email deliverability.
  • Relevancy Matters: Tips on creating relevant content that resonates with your audience to boost engagement.
  • Welcome Sequence Best Practices: Tyler’s strategy for a robust welcome email sequence to improve deliverability and engagement.
  • Avoiding Common Mistakes: Common pitfalls in email marketing and how to avoid them to keep your emails landing in the inbox.

Email Marketing Strategies for Better Deliverability Transcript

Rich: My next guest is the head email marketing nerd at Hypermedia Marketing. He has over seven years of experience running their email programs. He started out as a small marketing automation agency, then did full-time fractional CMO work, and decided to focus on what he loves best, email marketing. I am very excited to dive into email marketing strategies with Tyler Cook. Tyler, welcome to the show.

Tyler: Thank you for having me. I’m excited to dive into email as well.

Rich: So when I asked you what gets you jazzed up about email, you said something to the effect of helping businesses get their emails delivered. It seems like times are always changing and how we get these emails delivered is always changing. So can you give us a brief overview of the recent changes in bulk sender requirements by Google and Yahoo, and why they matter to us email marketers?

Tyler: Yeah. Last year, late last year, they announced that they were going to be making some changes. Both Google and Yahoo worked jointly on these changes, essentially together, even though they do have some slight differences on how they look at it. And they asked everybody to prepare for them with the three main changes being around DMARC records, spam complaints, and DKIM.

DKIM is essentially just a digital signature on the emails that say, yes, this email is coming from who it says it’s coming from. And DMARC is more of a security measure. And the reason why Google rolled out DMARC is one, they’re making a demark change on their domain. So you can’t send bulk emails from a Gmail.com address anymore because it will fail their demark record. But also it adds in an extra layer of security on the domain.

And then the last piece that they made an announcement for. Now this one wasn’t super big in the email circles, to be honest, because we all try to keep our spam rates down as low as possible. But it was good that they put a kind of hard line on it where they’re measuring at 0.1 percent is where they’re going to start getting concerned about you as a sender. And if you go over 0.3 percent spam complaints, they’re just going to stop delivering your emails.

Rich: Who are getting these spam complaints? So very often if somebody starts adding me to lists and I’m like, I never signed up for this list and I hit it. If I’m lucky, it goes to a page where I can report it. But I always think of those reports going to a HubSpot or a Constant Contact, not necessarily to Gmail or Yahoo. How are they kept in the loop with these things?

Tyler: There’s a few different ways that you get the spam complaints. So often if you’re doing a lot of cold outreach, you’re going to run into spam complaints, right? People don’t know who you are. They don’t know why you’re reaching out. You’re cluttering up their inbox.

Another really popular list growth tactic right now is essentially doing list swaps. And they can be valuable if done really well, but most aren’t doing them really well. And essentially that’s, I’ll give you my email list, you give me your email list, and then we’ll just email them. And that will also lead to a lot of spam complaints. So those are just a few ways that people are getting those spam complaints.

Now, one of the odd things is that when you’re looking in your email service provider, like HubSpot, or Klaviyo, Constant Contact, Convert Kit, all of those things, Google doesn’t actually push back the full spam report into those ESPs. So if you’re looking at that spam rate report and you’re seeing, a few spam complaints here or there, you’re actually probably gathering more spam complaints that you think you are. it’s just not getting pushed back into your email service provider. So you need to set up Google Postmaster to be able to actually see your true spam complaint as recorded by Google.

Rich: Okay, so you mentioned a few things. You mentioned this DKIM, DMARC. In an earlier call, you mentioned RUA tags as well. You’ve already said DKIM is more about where the email is coming from, if it’s coming from who they say it’s coming from. And then DMARC, can you give us a little bit more explanation about that? And maybe how do we improve that or how do we fix that if we’ve somehow gone astray? And then also what these RUA tags are.

Tyler: Yeah, so Google and Yahoo, they worked on these requirements together as a joint venture, if you will. And there are a few differences in how they are requiring DMARC to be rolled out. So for the most part, they’re the same.

However, when we look at Yahoo’s requirements and regulations and recommendations, one of their differences is that they are highly recommending, which is interpreted as, “will soon be required” an RUA tag. Now what the RUA tag is, essentially a DMARC reporting. They, DMARC, is monitoring where your emails are coming out from. And it really is helpful in understanding if somebody is spoofing your domain and sending invalid emails but using your information.

Now if you don’t have the RUA tag, the DMARC record is somewhat pointless because you’re not getting any of that reporting, right? You don’t know if somebody is misusing your domain for any reason. And that’s why Yahoo has highly recommended that you have that RUA tag so that you get the DMARC reports, so that you can analyze them and see if there are any nefarious actors potentially using your domain.

Rich: It seems to me these days, from both the businesses I talk to as well as our clients, that most people are using an email service provider, like the ones you mentioned, the HubSpots, the Constant Contact, MailChimp, Klaviyo, and so forth. Is it still our responsibility to do any of this work, or can we just expect these ESPs to take care of it for us?

Tyler: Do not expect the ESPs to take care of it for you. Unfortunately, a lot of the advice that I’ve seen from ESP platforms HubSpot, Klaviyo, Keap, ConvertKit, all of those the advice that they give has been accurate, but not complete. And so a lot of the DMARC policy or DMARC records that they’ve encouraged you to set up on your domain are incomplete DMARC records. Which as the DMARC policies come into play and there’s more regulations around how that DMARC policy record is installed on your domain, you’re going to have to go back and make multiple changes over and over again. Because again, where most of the ESP’s advice has said is they said here’s the DMARC record Here’s how to install it and then your policy is none. And that’s it.

They don’t encourage you to put an RUA tag They don’t encourage you to do anything else. The problem with that being that, let’s say next year Yahoo! says we are now requiring you to have an RUA tag Your ESP can’t set that up for you because they don’t want all of those DMARC reports. You want those DMARC reports. So now you’re going to have to go back and update that record again with an RUA tag, right?

And so don’t rely on your ESPs to, to set it up for you. Make sure that you know how to set it up and that you set it up as fully as you can.

Rich: Okay. What are some of the common mistakes businesses are making currently that are preventing their emails from reaching the inbox, above and beyond the DMARC, DKM, and RUA situations that you talked about already?

Tyler: Yeah, the biggest one, I guess the two big ones are going to be engagement and relevancy. So when I’m thinking about engagement and working with clients through engagement, oftentimes one of the first places that we start is by segmenting their list. We look at the segments that they have, we make sure that the right segments have been set up in terms of, who are your customers versus who aren’t your customers, who is engaging with you in a real way, who hasn’t engaged with you, who are your ideal customers that are on your list versus who’s not necessarily in that demographic. All of those things allow us to change how we communicate with them so that we drive up engagement.

So that’s the first piece that we look at. And then the second piece is relevancy. How are you creating relevant emails and relevant content and sending them out to your list on a consistent basis? What you think is really interesting and what you think your audience needs to know doesn’t always match up with what they’re interested in or what they want to know. And so doing that audience research to dial in on those topics, those real time questions that they’re asking, so that you can come in with an email and fully answer that question because it’s highly relevant to them.

Rich: All right. So let’s talk about that engagement thing. So this may be a total new question, but are you telling me that my ability to get my emails into the inbox of my ideal customers who have opted into my emails is often based on how engaged people already are with my emails? That’s one of the factors that’s going to improve my deliverability?

Tyler: Yes. So this hasn’t been confirmed expressly by Yahoo, but I manage enough email lists that I’ve seen this really consistently across millions of emails at this point. For Yahoo specifically, if a subscriber has not engaged in about 80 to 90 days, I’ve seen where Yahoo will start throttling your deliverability to Yahoo domains. And so that engagement piece is very critical now.

Rich: And when you say ‘throttling’, does that mean that it’s just not being delivered? And I’m not a Yahoo email user, so I don’t know if they have the same promotion tabs like they do for Google. Does it end up in their junk folder, or is there another way that Yahoo throttles those emails so perhaps people aren’t getting them?

Tyler: Good question. So throttling can happen in a few different ways, depending on previous engagements. So what I’ve seen is if you’re emailing a segment of Yahoo subscribers that have never engaged with you, and it’s been about 90 days since they’ve been on your list, typically those emails will just never be delivered.

However, on subscribers who do use Yahoo and they have engaged with you sporadically, then yahoo really doesn’t know what to do with those. And sometimes they’ll make it to the inbox, other times it gets ignored. And essentially what Yahoo is trying to figure out is, does this person really want your emails? And if we send this to the spam folder, do you search it out?  If you search it out, great. Then let’s send you back into the inbox. If you never think about the sender again, we’re just going to stop delivering them.

Rich: All right. So Tyler, and I know I’m asking for specific concrete results or answers that you can probably not provide. But based on what I’m hearing from you, a good approach to email marketing would be is if somebody joins my list, and on day 89 if they have not engaged with any of my emails, my best thing would be to have an automated email go up that says, “I guess you don’t want to hear from me. If you do, click on this link and re -engage, otherwise, we’re going to take you off our list”.  

Because then I don’t have to deliver anymore, and I won’t be hurting my engagement rate, as far as Yahoo seems to be defining it. And I know I’m asking you to be looking into the Features edition book of Yahoo email marketing at this point, but is that kind of what we’re getting to?

Tyler: At a minimum for clients, when I’m setting up something like that, we actually trigger that around day 60 of no engagement. Because there are other strategies that we try to implement to win them back. And those are some more advanced strategies of also using what I call ‘secondary channels’ like LinkedIn, Instagram, where you’re trying to communicate with them outside of email to try to win them back inside of their email inbox.

Rich: And are you doing this using social media as a secondary channel or back channel, are you doing this through retargeting of ads, because you have their email list and you’re building audiences? Or are you just telling your clients to manually engage with them one-on-one via LinkedIn Messenger to start that conversation with the hope that then they’re going to open up your next email?

Tyler: Manually engaging with them. It’s part of the strategy that we use, where when a new subscriber ops into the list, one of the emails – usually the third in our welcome flow sequence – is an invitation to connect on a secondary channel.

Meaning Instagram, giving the page a follow, the person to follow can connection request on LinkedIn, page follow on Facebook. Just somewhere where we can 1) measure the impact how, many people are actually helping us grow our following on that social media channel. And then 2) is there a direct messaging feature?

So we do that very first so that then if we have future problems, we can use that secondary channel to win them back.

Rich: All right, very interesting. Obviously, very hands on. And then you mentioned relevancy being another one. Which, on the surface of it, seems so obvious. Of course, we should be sending relevant emails. Why bother, otherwise?

What are some of the metrics or the KPIs that you recommend that we look at? Is it open rates? Is it click through rates? Is it social shares? What should we be looking at to determine relevancy for emails?

Tyler: Yeah, great question. So the best metric that I’ve found to measure relevancy is going to be replies, or if you have some sort of follow up sequence. So an ‘opt in’ can also work. So if you’re doing a campaign for a five-day challenge, how many people are actually opting into that, or asking them to fill out a survey. Anything where there’s an additional action.

Unfortunately at this point, open rates are highly directional. They’re unreliable, but they are a good directional metric to understand if, as a whole, your content is in the right direction or not. And then even with click throughs, because of the rise of bots and different things that mailbox providers like Google and Yahoo are doing, even click rates are not reliable. And so really, the only reliable thing to measure are going to be what I said, replies back to an email, asking somebody in that email to fill out a survey, and they fill it out having them opt in for additional piece of content, those types of things.

Rich: All right. Now I’m going to switch back to Gmail, which is my platform of choice as a user. Often when we do send out emails, even if they are delivered they end up in that Reddit promotions tab. How can we get out of that neighborhood and into a more desirable neighborhood like the inbox?

Tyler: Yeah, great question. So again, a big piece of this is going to be email content and engagement history. One of the first things that I always recommend for all of my clients and we set this up, is getting a reply back to an email as quickly as possible.

So typically speaking, when somebody opts into the list, the very first email that they’re going to get is going to be a very short email along the lines of, “Hey, I noticed you just opted in for this resource. Were you looking for more information about it? Just hit reply and let me know.” And you actually will get a very good reply rate off of that.

Now, the reason why I recommend replies is for two main reasons. One, is it builds that internet highway network, if you will, in a very robust way. So if somebody replies, Google takes that email more seriously, and it’s much more likely that you’ll land in the inbox going forward.

The other thing is we’re actually hacking Gmail’s user’s settings by getting them to reply. So Gmail has a convenience setting that is turned on by default, and most people turn it on anyways. But what it is, it’s a setting that says essentially, if I email somebody back who is not in my contacts, automatically add them to my contact list. Add them as a contact. And so if you’re sending out that marketing email and you get somebody to reply back to you, now all of a sudden your marketing email is now added as a contact in their address book. And we know from Google that contacts who are in their address book have priority and will more likely land in their inbox.

Rich: Okay, that’s good to know. Now you mentioned the welcome sequence a couple times. One, first email, let’s get a reply. Third email or so, you are trying to get them to connect with you on a secondary channel. You go social. Are there other elements to a successful welcome sequence that you can share with us? Maybe the length, the frequency, or calls to action that should be included in some of these messages?

Tyler: Yeah. So the welcome flow, in my opinion, really has three goals. The first goal is to improve deliverability overall, and then extend the amount of time that your emails land in their inbox. The second goal is going to be to train the email algorithms and promote engagement. And then number three is, hopefully it’s making you money. It’s moving people down that sales pipeline, if you will.

So there are a couple of really specific emails that we have sent out. Email number one is generally always asking for a reply. Email number two is more of the mission of the company, but we’re also using that to establish expectations. And what I like to do is I like to make the email situation sound like we’re going to email a whole lot more than we actually do, just so that they’re pleasantly surprised and they don’t mark us as spam in the future.

So one of my favorite sayings in that email number two is something along the lines of, “We are a high-volume sender. We typically send you an email every single day. Sometimes we’ll send more if we’re promoting something. So just want you to be aware of that. And if you don’t like that, go ahead and unsubscribe here.” But what that does is even if you only send three times a week, your subscribers are pleasantly surprised because they were planning on a daily email, right? So that’s email number two.

Email three is a secondary channel connection request. And then email number four, I just call it the ‘new subscriber survey’. And the purpose of the new subscriber survey really has three goals. It’s first to see who is joining your list and should they be on your list, right? So you’re trying to get some demographic type of information, trying to see if they fit within your ideal customers.

Goal number two is to find out what content and topics are relevant to them. And then number three is we want to try to create what I call advertising efficiency. So we want to figure out where did they come from, who else do they follow for information as it’s related to you? Are there any active communities or associations that they pay for that if we just started showing up there we could find more of our ideal clients?

And so we send out that new subscriber survey to accomplish those things. And then typically email number five transitions to a sales email, which we have some testimonials, social proof, and then a soft call to action.

Rich: Nice. All right. That’s a very clear flow for sure. Now, one of the things that I see out there is the idea of a double opt in for new subscribers. Is that still a relevant technique these days?

Tyler: It is. It is still a relevant technique. I am not a fan of it. Mostly because I think it weeds out quality subscribers that just don’t want to go back to their inbox and click on a link. Or for whatever reason they don’t get that, or for whatever reason they get distracted and then they never come back.

What I like to do is I actually like to use the welcome series, that welcome flow, as a five-day double opt in period. Where one of the things that we’re measuring is if you haven’t taken any action, if you haven’t opened any emails after that initial welcome flow, we will move you oftentimes to a suppression list inside of the email service provider. Because if you haven’t engaged in about a week on any one of those emails, it’s not likely you’re going to engage on any future emails. So I actually I’ll turn off double opt in, and then I use the welcome sequence as a fake or faux double opt in, if you will.

Rich: I was going to ask you this question earlier when you were talking about it. But you mentioned – we’re a high-volume email sender daily, maybe more than one – for businesses that are only sending out once a week, once every other week, or even once a month, is that a negative then to send out so quote unquote “infrequently”?

Most businesses, I guess it depends on the business. If you’re out there selling a whole bunch of widgets or things like that, then a daily email probably makes sense. But if you’re more in the kind of consultative arena, then people probably don’t need to hear about their taxes every single day or whatever you may be an expert in. Is there a different approach you might recommend if people would only be sending out an email every other week say?

Tyler: Yeah, great question So one of the things that does impact deliverability and inbox placement is volume of email. And what we found from some pretty extensive testing, not only internally for our agency but just working with other email agencies, is Google and Yahoo and Outlook like to see levels of consistency And so it’s better for you to email more often and more regularly than even every other week, even if you think your audience won’t respond well to that.

Now that gets into, how do you find and source relevant topics? And so one of the things that we look at is we call it a primary content. So these, this is going to be content that is directly related to whatever your product and service is. So if you’re talking about taxes, there’s probably 10 to 15 topics that you could be writing about that all relate back to what you do for taxes that your audience would be interested in.,

Then we also have what we call secondary topics, which people are still interested in, but they’re not directly related to what you have to sell. And so this could be let’s say that you do run taxes, and your audience is younger families. You could probably mix in parenting topics into your email cadence, and your list would respond fairly well to that because of their stage of life. They probably have young kids, they’re going to be receptive to it.

Now that doesn’t mean that you should go, full bore, full speed ahead on just doing parenting stuff because it doesn’t match with your brand. But talking, having a few emails about how to talk with taxes about your kid or how to talk with your kids about taxes. That would be a really interesting topic for a lot of people, not necessarily directly related to what you sell, but it’s that secondary topic.

Rich: Yeah. And you’re setting yourself up as a trusted advisor in that space, too. You had mentioned early on in the conversation, you need to have list swaps and how most people don’t do it right. And I had never even considered giving my list to somebody else and vice versa. But I almost wonder if this is an opportunity if you are struggling to come up with all that content, where you might do a content swap. Where I might have you come in and write to my audience, say strictly about email marketing, and you might have me come in and talk to your audience about Spider Man or something like that if it was relevant. Where we would just be getting the equivalent of blogging guest posts to come in and write an email, and in that way be introducing ourselves to each other’s audiences.

Tyler: So right now, let’s just say email advertising is highly underpriced. It’s about where influencer marketing was in probably, 2014, 2015, 2016, where if you can find a few partners like that, that have a sizable email list, typically you want to look for anybody who has at least 5,000 to 10,000 subscribers on their list for this to make a meaningful impact for you.

But having that content swap, whether it’s paid, whether it’s free, because you’re promoting each other’s businesses, it’s an excellent growth tactic and one that I’ve used to grow a few e- commerce businesses from zero in revenue to $1.5 million in revenue in 18 months. The primary driver of that was actually advertising in newsletters. And then also a few different projects that I’m working on. We’re growing primarily through getting in front of other people’s email lists.

Rich: All right. Now a lot of people might be listening and saying, I’ve let my email list go dormant, it’s stagnant. It’s either not growing or I haven’t been sending out regularly. What steps could they take to rejuvenate that email list?

Tyler: So the first thing that I don’t recommend is, don’t write up an email and send it out to everybody right now. That will do more harm than good. So the first step is to segment the list in really small segments and do essentially what’s called a warmup period. So typically, we’re going to slice and dice that list to really small groups of just 50, 100, 150, 200 groups of people. And then we’ll start dripping out content to them to see how they respond.

And we’ll also, I’m a big fan of the email that’s saying, “Hey, it’s been a long time since we chatted. Been really busy, learned a lot of really cool lessons. Here’s the way that I help all of my customers.” You want to let people know what to expect from you. “So here’s how we help. Here is three things that you could do today that will help you take a step closer to whatever goal you want to achieve. I’m planning on sending more emails out. If you don’t want to see me in your inbox, go ahead and unsubscribe using the link below.” And that’s actually a more effective email than you would think.

Rich: All right. But do those in small batches, so you’re not signaling to the system that nobody cares about my content anymore. You’re just testing the grounds to see how things are received. Correct?

Tyler: Yeah. And you’re also playing a game between positive and negative signals, which we didn’t really get into. But if you send it out to 50 people and none of them open, that will do less damage to your domain than if you sent it out to a thousand people and none of them opened.

Rich: That makes a lot of sense. This has been absolutely fascinating, Tyler. And I’m so excited to get back into my email, but absolutely not sending out emails to 10,000 people at a time. And we’ve been good about it, but I can tell that we have opportunities for improvement, as I like to talk about, especially around our welcome sequence. So this has been fantastic.

If people are interested in working with you and improving their email deliverability and making more money off their email, where can we send them?

Tyler: Yeah. So the first place, go to my website. Anybody can book a call with me off of my website, and we can run through an email audit, we can talk about deliverability, we can talk about what it looks like for us to come in and manage the list.

And then the second place that I would encourage people to go is connect with me on LinkedIn. I write really often about different strategies, different things that we’re testing, promoting that content on LinkedIn as well.

Rich: Awesome. And we’ll have those links in the show notes. Tyler, thank you so much for coming by. I’ve learned a ton, and I really appreciate your time and expertise.

Tyler: Thank you for having me. It’s been a blast.


Show Notes:

Tyler Cook and his tram at Hypermedia Marketing has helped countless businesses grow and scale through proven email marketing strategies. Check out their website to see if his team can help with your email deliverability issues. And be sure to connect with Tyler on LinkedIn, where he shares his latest strategies and tactics.

Rich Brooks is the President of flyte new media, a web design & digital marketing agency in Portland, Maine, and founder of the Agents of Change. He’s passionate about helping small businesses grow online and has put his 25+ years of experience into the book, The Lead Machine: The Small Business Guide to Digital Marketing.