The Right Message To The Right Person At The Right Time: The Secrets To Effective Email Marketing With Dean Dutro

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TBT 154 | Email Marketing

Some people say email marketing is dead. Nothing could be further from the truth. In reality, email has become more nuanced as a marketing platform and it remains the single best way that you can reach the people who want to listen to what you have to say. Dean Dutro explains this in more detail in this conversation with Penny Zenker. Dean is the co-founder of Worth eCommerce, a marketing firm that specializes in helping eCommerce companies increase their revenue through sophisticated email and SMS marketing solutions. Listen in as he explains the unique advantages that email has over other popular media and how you can use it effectively to increase your leads and grow your sales in a relatively short time. He also shares his unique focus on performance management in lieu of time management, an interesting strategy that works perfectly in his company’s business model.

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The Right Message To The Right Person At The Right Time: The Secrets To Effective Email Marketing With Dean Dutro

We’re going to talk about email and SMS marketing, and how you can break through this seemingly simple yet complex strategy of how you can gain more prospects and nurture those prospects into clients. I have an expert with me, Dean Dutro. He is the Cofounder of Worth eCommerce, a seven-plus-figure eCommerce marketing agency that helps businesses of all sizes to grow dramatically, and grow their revenues at least 30% with this lifecycle, email marketing and SMS marketing. He’s also a Premium Partner for Klaviyo and sits on their advisory council. He’s a Founder of Email Growth Training and has helped over 600 stores growing by leveraging their email. We brought the expert to you. I hope that we’re going to not only answer your questions, but we’re going to provide you with some hot tips that are going to help you to advance your email marketing strategy. Dean, welcome to the show.

TBT 154 | Email Marketing

Email Marketing: The average ROI for email is $38 to $42 for every dollar spent, which is the highest for any channel.

Penny, Thanks for having me. I’m excited to be here.
This is one of those topics that is important and interesting because email marketing seems simple, and it’s very little cost to entry, yet it’s a hard nut to crack to get it to work for you. I’m excited about what you can share with us.
It’s one of those things where when I talk with business owners whether they’re an eCommerce, B2B, run a retail store or whatever areas is they know they should be doing it, but oftentimes they haven’t set anything up. If they set it three years ago and forgot about it. I also want to make sure that the email I’m talking about is not a cold email. It’s not reaching out to a list of people. These are people that are coming to your site and coming to your business, and giving you their information versus a cold email. I want to make sure I make that difference.
You’re saying it’s not for the people that you bought a list and you’ve got no relationship with them. It’s people who want to hear what you have to say. That is an important differentiation because it’s a different conversation.
Different conversation and different strategies. One of the stats that I love to talk about that gets people’s ears to perk up is that across industries outside of eCommerce, B2B or wherever, the average ROI for email is $38 to $42 for every dollar spent, which is the highest ROI channel. There are a lot of reasons for that that we can get into. That’s something that people should know a little bit more about.
Let’s give a scenario. When you talk about this list of people who are actively interested in what you have to say, there are a lot of people who have multiple email accounts. I have an email account simply for things that I sign up for. I’m interested but at the same time, I’m not checking that email all the time. I want whatever that thing was, but I want to control the relationship. I want to get right into some of the nitty-gritty about some of the challenges. How do you engage with someone like that?
Email is about sending the right message to the right person at the right time. It’s the same with SMS. There are a couple of different things that we have to tease out to understand the strategy behind getting to that scenario. One is there are your automated emails, which are called automation, flows, sequences or drips. There are a bunch of different names in any email platform. Those are action-based and timing-based emails that you would send. They’re often built around or should be built around the customer life cycle. To me, the customer life cycle is essentially the same across businesses. You’ve got prospects, new customers, repeat customers, engaged or VIP customers, lapsed prospects and lapsed customers.
Where you were falling into that scenario are the lapsed prospects. You’re someone who was interested, but you want to control the experience and the relationship. Maybe you’re not ready to buy yet, but you still want to hear some things going on and see what’s happening. Maybe you’re waiting for Black Friday or your birthday. What’s interesting about email is you can create that segment of lapsed prospects. Let’s say there’s someone who has previously engaged with you. They opened 1 to 3 emails in the past.
They haven’t opened that many emails in the last 120 days. You could make some assumptions that they either aren’t interested or they went to a competitor. You haven’t touched on what are their objections to purchasing from you or reaching out to whatever your goal is. You test those assumptions. You could say, “This lapse prospect, there are three reasons why they aren’t purchasing. I’m going to send three different emails, touching on each of those reasons to try and get them to overcome the objection.” That’s one way you could go about it. It is knowing they’ve opened in the past, they’re still getting your emails, and then figuring out what messaging is going to get them to open and click again.
There are a lot of good things that I want to break down for people. The first thing that you said was you’re breaking the list of people that you’re interacting with down into segments. Each segment, like you said, prospect, new customer, repeat customer, lapsed customer, they’re all different conversations that you want to have and be able to customize. I want to highlight that for people because the first mistake that people is they try to talk to everybody in the same way.
How many emails have you got from Best Buy where it’s a list of 100 products and a big sale, or West Elm or any of these big department stores? You’d think they’re good at email. They’re not as good as they could be. You see smaller brands and more intimate brands that are connecting with people, getting higher conversion rates, higher open rates and things like that with new technologies. The conversation you’re having with different parts of your customer life cycle should be tailored to that avatar of who that person is. It doesn’t sound complicated.
The conversation you're having in different parts of your customer life cycle should be tailored to that avatar of who that person is. Click To Tweet It’s not, but go ahead and say what you wanted to say around that for people who feel like, “How am I going to do that?”
It’s a time commitment. It’s either you got to write the email, you got to get someone else to write it. What it comes down to is you understand your customer avatar. You understand at certain points in their relationship with you, they’re wanting or needing certain things. Prospects, for example, you want to build trust, authority, social proof, and offer some guarantee. What are the methods you can use to indoctrinate them into your brand, so they go to you versus a competitor? You could Google trust-building techniques and apply that to email, even SMS to a certain extent where you’re developing that trust with people.
I wanted to come back into the second part when you were talking about segmenting them and then having that conversation, and then you said, “Test some of your assumptions.” I’d like you to speak a little bit more about this testing because people think, “You’re going to tell me how it’s going to work. I’m going to do it and it’s going to work.” That’s a myth.
Yes and no. I’m a big believer in 20/80, the Pareto Principle. I imagine you are familiar with that. One of the things is there are certain assumptions at work. You can assume that if you want to increase the chances of someone calling you, purchasing on your site, coming into your office or whatever your goal is for your business, that if you can increase trust, then they’re going to be more likely to take that action. You know that you can increase trust by social proof, offering a guarantee, talking about yourself, being open and making it easy to contact you, things like that.
Where it starts to matter as your list grows and as you want to max out your ROI, then that’s research to test these little nuances and figure out, “What form of trust-building works the best for my customers? Do they care about a guarantee? Do they want to know the founder and the story behind it? When is it appropriate to share that?” There are general assumptions that can be made, and then as you grow, you figure out which assumptions appeal more to your list and prioritize those.
We’re talking about the content of the email. What are the important stats that people need to look at when they’re going to run an email campaign and whether they’ve segmented it or not? What are the key things that they want to look at to see if it’s working and see where they need to optimize it?
It’s a nuanced answer. I’ll give the broad picture and then dive into a couple of pieces that I think are important. Overall, you have to look at how Gmail, Yahoo, AOL and Outlook work in terms of how they provide an experience to their customer. It’s easy to get banned, spammed or put directly in the trash. There’s an interesting measurement that is Gmail, and this number has changed over time. It considers someone engaged with your brand if it’s happened in the last 120 days. If it’s past the 120-day mark, often your emails are not going to go to spam, but they’ll go straight to trash where people will never see them. Google is assuming that the person isn’t interested. It improves the overall experience. I often tell people like, “Check your trash in Gmail. See if there are any companies in there that you used to be interested in. It’ll surprise you.” It’s the difference between trash and spam. That’s the timeframe you have to actively send the right message and engage with people. There are ways around that.
Let me ask you while we’re in the segment of getting your email received. Somebody came onto my site and they downloaded a report. In that 120 days, how many times should I be connecting with them and what are the timeframes?
In that case, you call that a welcome flow. They’re interested in your brand. They want to learn more about it. You’re probably going to want to have at least five emails that each of them has a specific goal. Going back to that prospect, what’s important to them? Is it the information about your brand? Is it trust-building through a message from the founder where it looks like a text-based message being sent from their email? Could it be a video? There are all things you could try. Video and text-based emails work well. There are a lot of fancy email designs out there. It’s harder for those to work because there are many different email platforms now.
What you want to look at are your average open rates and make sure that within the automation, let’s say you send email-1 immediately, email-2 a day later, email-3 two days later, email-4 two days later and so forth. You do it all within 10 or 15 days. If you notice that any of those emails drop under 20% open rates, you either want to A/B test it or pause it. If you notice after five emails, your open rates are still 30% or 40%, you should continue adding more emails to that flow until it drops off to about 20%.
That’s a high open-rate percent, don’t you think?
If they’re interested in your brand, 20% is a good baseline. I’m talking about automation. Your manual campaigns may be different, but your flows should be above that mark in a lot of ways. If they’re not, then your emails might be too long. Your incentive to join the list isn’t a good fit for them. There could be various reasons, but that number is industry-wide as I’ve looked at it.
At least they’ve come to you. You can expect that you should have at least 20% in terms of people opening. Does that drop after the first email, do you find?
Yes, for sure. If you’re offering a PDF, for example, that first email should be pretty high if they’re interested and it’s a good traffic source. It’s a good idea to make sure that for any incentive you offer, people have to check their email to get it versus download it immediately. The reason why is that that first email is going to be the most received and most opened email that you’ll ever send. If you’re getting 60% or 70% open rates on it, your open rates across your email systems when you send a promotion or a discount offer will trickle into higher open rates across the board, which is interesting.
What about click-throughs now? I’ve got this call to action for them to click on this and make a meeting with me. How about on that side? What kind of expectations should we have?
That varies so much. That should be one of the first things that you A/B test are your click-throughs. It doesn’t have to be a major change. It could be a call to action that looks like a button or a link, and see what people resonate with. As those win as you figure out if there are any differences, any campaign you send later, you should leverage that information, knowing that your list is more likely to click a button versus a link. It depends on the goal of the email. You could have an email where your goal is to get them to read the email versus click-through to something. You’re not caring about the click-through because you want to make sure they’re opening the email and reading it. I don’t tend to look at that too much. I tend to look more at open rates and flows. I’ll throw in some A/B tests for the click-through.
For those who are reading, A/B testing is what? Can you describe that in case they don’t know what that is?

TBT 154 | Email Marketing

Email Marketing: There is a myth that pop-ups annoy people. The reality is people expect to see a pop-up, just not a crazy amount all the time.

It’s taking the same email and putting a slight variation to it. A subject line change or a click-through change, but only one at a time. You could do multivariate where you’ve got five emails, each testing different things. If you have to have thousands of visitors coming to your site and going through them to get any significant data, it takes a lot of time to see any results. Going back to 20/80. It’s to get the foundation going first. Most people make the mistake of not having any emails. I always say, “Let’s get this foundation up and worry about A/B testing later,” because it can be pretty overwhelming to learn stat analysis, if there is an accurate measure of results or not, and what that looks like in a spreadsheet. It’s like, “Let’s just start with the foundation.”
We talked about some myths and mistakes that might be in there from people. What do you see as one of the biggest mistakes that people make that we haven’t discussed?
We’re going to talk about email capture. A lot of people never put up a pop-up on their website because they think it annoys people. Ninety percent of people coming to your site expect to see a pop-up with some incentive, especially in 2020 or 2021. You got to get some email capture, some form going where you’re capturing emails at a significant rate versus just a contact form or things like that. If you’re using a contact form, you are never going to leverage the full potential of the visitors coming to your site if you’re driving traffic and things like that.
You want to be giving them something of value. Something that is creating that desire to download that.
The myth is that pop-ups annoy people. The reality is people expect to see a pop-up, but not at a crazy amount all the time. Once they’re on their site for 7 to 10 seconds, that’s a good amount of time where they’ve looked at your site. They’re already interested. Give them a little incentive to stay longer.
I wanted to talk about SMS marketing and then I want to ask you some general productivity questions. Which is better, SMS versus email? Some people think email is dead.
Email is not dead. It’s the first form of digital advertising that ever existed. I think it was an auto body shop that sent the first email to people in his region. What’s interesting in 2020, more people were opening emails than ever. There’s a reason for that. It becomes a lot more nuanced. It’s circling back to the right message at the right person at the right time. Companies are getting better at targeting their email list so it’s something you want to open. They’re designing it better so people can read it. That’s helped a lot, knowing when to send to what customers and what to send them. In terms of SMS and email, there are many different layers to what’s better or not.
What I like to look at is the overall lift. Some companies are able to directly measure revenue produced by email or SMS than eCommerce companies. Some companies measure, “Am I getting bookings? Are people coming into my dental office?” Whatever your industry is, you’re often going to be measuring something. What you want to do is make sure that email and SMS work in alignment with that same principle of right message, right person and right time. If they see an email and an SMS message on the same day, they’re going to be way more likely to convert into the action you want. That being said, not everyone is going to give you their phone number and email. They may choose one or the other. A company that does this well is Hydro Flask.
If you go to their website, there’s a pop-up that shows up. They are beautiful. You enter your email first, that’s called a micro-conversion, then they ask for your phone number, which is a bigger commitment. Even if not everyone gives you their phone number, you’re still collecting emails. That’s one strategy. You can also look at your demographic market and see, “Are my customers are Baby Boomers, Gen Y, Gen X, Gen Z?” Whatever they are and whatever the research will say, which I believe that a lot of Baby Boomers love using a text message because they don’t have to log into anything. They don’t have to log into their email and see all these emails. They’re getting a text directly to them, and they can respond to the companies with immediate feedback. That’s the key to making SMS work. The key to making SMS work is it has to be a two-way communication channel where someone in your company is responding to these messages. That’s going to lead to a massive increase in conversions for you using SMS.
I would imagine that everybody has a preference. Some people would prefer to get an email. Baby Boomers might be one and Gen X might be another. I would think with the statistics that people are checking text messages within two minutes of receiving it, it creates that immediate receiving and potentially the immediate action of, “Let me take a look at that and see what that is.” Is there a way that you can track click-throughs on your SMS texts?
There are a ton of software out there for eCommerce companies like PostScript. For B2B, ActiveCampaign allows you to send messages, text messages and emails. Companies are starting to incorporate it. Adoption has been slower with the mental block being, “Should I capture email or phone numbers? Do I have the capacity to respond to text messages?” Most people don’t respond to emails. You could send out 50,000 emails and get 5 to 10 responses. You’ll notice when you send out text messages, you’ll get a lot more, which is that two-way communication.
Let’s go to the overall productivity topic. You’ve built this successful business. You’ve had to juggle a lot as your business has been growing, scaling and working with other businesses. What’s the shortcut for you that helps you to be more productive day-to-day?
We grew our business fast in 2020. We’re 50 employees and we’re all virtual. There are three core things that we look at. One is the Pareto Principle. What 20% of our activities are leading 80% of the results? We do that for each team member. That goes for our leadership team all the way down to our administrative team, and figure out how we are going to push the needle forward. Every quarter, we’ll do a 20/80 exercise where we spend 1 to 2 hours listing out every single task we have. Every quarter, those tasks will often change. As your company evolves and grows, you’ll learn new things. I’ll have 50 tasks. I’ll weed it down to 5 or 10.
Those tasks either become a job opening in my business or I hand them off to someone else. That has been exceptional in our growth. I got this idea from Mike Michalowicz who’s on our podcast. He’s a great business author. He wrote Profit First and The Business Hierarchy Of Needs. He talks about if you take those tasks and create a job posting out of it, you’re going to get the perfect person to apply for it. It’s one quick win that you can implement in your company. We’re getting the talent that wants to do the work that you don’t want to do. You don’t even have to delegate because they’re wanting to do it, which is a sweet way to grow, and then leveraging your team. Figuring out who’s good at what and making sure they’re driving the needle forward.
For me, I love The Best Self Journal. I’ve got dozens of those. We buy them for each of our customers and a lot of our team members. Their approach is simple which is, “What are the tasks for this quarter? What are the three things I need to focus on? What are the three things I learned?” That’s then clutch in terms of focusing my mind on where to put my attention and where to grow. Those things have been excellent. From a tactical standpoint, I use email to scale myself. I have my team use email to scale themselves. We have 100 clients that we work with. Instead of calling each one of them to thank them for joining, I’ll send an email with a video directly thanking them for joining. It’s a similar effect, maybe not as good as calling them, but once clients reach a certain threshold of revenue or time with us, I will give them a direct call so they can see my face. Also, having a podcast, being able to spread that knowledge to our team, to our clients and to prospects has been huge in terms of leveraging my time.
Email is not dead. It’s the first form of digital advertising that ever existed and yet more people are using it now than ever. Click To Tweet What it’s all about is creating that leverage. I do a similar type of exercise with the Pareto Principle. It’s something so simple and key that people get caught up in all there is to do. The fact is not all tasks are created equal. We have to remind ourselves and our team so that we stay focused on the most important thing. It’s quite interesting. You say you do this with every team member. I often hear that there are possibilities for people like yourself that are running the company. You can always delegate and you can create the job opening, but do you do that for somebody who’s on your team who has their 50 tasks, and there are five that are the most important? What do you do with their things? Do you continue to create an extra job? How do you empower them? That’s always the question. It’s like, “Yeah, but my boss makes those decisions and it’s out of my control.”
What I realize is there’s the ideal state of what you want to be working on and there’s the reality state. The reality is you’re not always going to be able to focus on 3 or 5 tasks. There’s always going to be certain things that happen, but it’s about maintaining that focus. Most of the time, you are. When it comes to team members, they’re not going to see it the same way in terms of creating a job opening. You got to put that vision in front of them which is, “If you do perform at a level that grows the company revenue-wise,” then tie it to their goals. Whether it’s financial, buying a house, running a marathon or whatever they are, you can tie that to their position and say, “If you meet these goals, here are the perks.”
If you want to become a leader, delegate to people, and lead people in other ways, you can. If you want to get great at your skillset, you can. Not everyone is the same in that regard, but it’s that ideal state and that vision that inspires people. The reality is there’s always going to be work that is outside of that and it’s minimizing it. If you’re managing by time, it’s hard to think that way, but if you’re managing by performance or leading by performance, then you start to see there are many tasks that they don’t even need to do and you could outsource to a VA. Not every single 28 is going only to a new job opening, but it could.
The key to what you said is that you’re helping people manage performance versus managing their time. That’s one of the key things that I look at as well. It’s a different perspective and a different mindset. When we run ourselves in our businesses and help our team to work in that way, we get different results.
That question you asked, I’ve thought about it, and I don’t think I’ve formally written it down or thought too deeply about it. It sounds like you’ve worked with that or had that question in the past. I’m curious about your thoughts on it.
Questions about people at lower levels and what they do?
Yes, about the 20/80 for them.
There are a couple of different things. One is when that person becomes aware of what’s most important, they may come up with great cost-saving and time-saving ideas. They may come up with ways to automate it, or you have to empower them to empower the organization to also make change where necessary, not just to necessarily create a new job position but also to change a rule. There might be some rules that are inefficient in the way that people work. Maybe there’s something that you could change. I encourage people if they feel like they’re not in control to imagine that they were, and what kind of conversations could they have with their direct reports, showing them the more value that they could deliver if they focused on this and here are some ideas. Maybe even create a workshop together. Ask their boss or their team to create a workshop to talk about how to handle all of these things that are outside of the core.
It could be a VA, somebody part-time or a system that could handle it. By bringing in some software, it could help to automate or reduce the time that it takes to do certain things. It’s empowering them. It’s the vision but giving them some tools to figure it out and understand the business. There’s an equal part from the individual and them putting that hat on, but also from the organization to be open to change and to provide some tools and structures like you’re doing for your team to think about it in that way. It was great having you here. You gave me some difficult questions and scenarios. You brought some great tips and tools. Before we close out and you tell people where they can access you, is there anything else that you wanted to share that we didn’t touch upon?
Email is one of the biggest missed opportunities for most businesses to leverage their own time and scale themselves. Getting started, setting up a few emails, a few flows and a cadence over time will dramatically improve the results you want to see. I’ve seen it helped many people. The other key point to it is that having an email list is also a form of protection for your business. There’s an example I want to give. One of our clients had this massive Instagram following, and most of their revenue came from Instagram. When he joined us, he didn’t have an email list. We started building it and we built it for 50,000 people. Instagram changed its algorithm and his account got banned, which means he lost about a million followers, which was the main source of his revenue. Luckily, we had put an email system in place that had about 150,000 emails on it now after about 1.5 years to where he could still earn a living. That’s the other key, is that your email list protects you when Google or Instagram or whatever changes.
YouTube, Facebook, I’ve heard across the board that that’s happened to people.
I’ve seen many companies where they’ve come to me, “My accounts are gone.” For no fault of their own, just a simple algorithm change. Email has been that lifeblood for them. I call it owned marketing. It’s their owned data. Download your lists whenever you can. It’s a good thing to do.
Where can people reach you, find out more about you and the services that you guys offer?
We work primarily with eCommerce companies, but I’m open to talking to all business owners and a part of different business masterminds and groups like that. You can find me at You can also find me on LinkedIn at Dean Dutro. If you’re interested in our service, just go to There’s a little chatbot there that you can check out or contact us through a form there.
Thank you, Dean. I appreciate it.
Thanks a lot, Penny.
Thank you all for your attention. Hopefully, you’ve been taking notes. A couple of simple but important tips about how to maximize the way that you’re using email. First of all, do it. Make sure that you’re collecting the email and you’re capturing them. We talked about understanding how they’re being received so that you know that people are receiving them, they’re opening them, they’re clicking through them, and make sure that you’re segmenting them and having the conversation with the right people at the right time, and the right message. It sounds simple and it is when you prepare it and you bring on some expertise to make it happen. Your next step is to evaluate what you’re doing with email, how it’s working for you, and taking that next step to optimize it to take it to the next level. We’ll see you all in the next episode.

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About Dean Dutro

TBT 154 | Email MarketingDean Dutro is the Co-founder of Worth eCommerce, a 7+ figure eCommerce marketing agency that helps businesses of all sizes dramatically grow their revenue by at least 30% with lifecycle email marketing and SMS marketing. Dean is an eCommerce email marketing and SMS expert, a Klaviyo Platinum Partner, and sits on Klaviyo’s Advisory Council. He is also the Founder of Email Growth Training and has helped over 600 stores grow leveraging email. He is also the host of the Relationship Commerce Podcast, that focuses on eCommerce founders, their stories, struggles and strategies that are working to scale now.
Dean holds a Degree in Communication Studies from the California State University-Long Beach.

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