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Top 10 Challenges with Email Automation and How to Overcome Them

Discover a set of best practices discussed by eCommerce and Digital Marketing Experts and learn how to overcome the top 10 challenges with email automation.

This article will help you get the most out of your automated emails / customer outreach strategy. My co-founder and I have a background of over 6 years in eCommerce. We started off as newbies, learning everything on our own as on the go. Started with Facebook Ads, just like everyone does. But soon realized we needed to switch our focus on independent marketing channels like email marketing. One thing that we knew from the very start is that we wanted to make our customers feel special at every step of their shopping journey. During this time, we have helped dozens of eCommerce stores, including our own, grow sales using automated emails and we'd like to share what we learned from the experience. 


To make this article way more powerful and valuable for you, in the past couple of weeks, we’ve been talking to 10 industry experts aiming to put together a set of best practices for email automation. Our main goal was to go beyond recycled content usually found in blog articles and what you are about to read is definitely doing that.  

These are the things that no one actually talks about and that we wish someone told us before we started our eCommerce journey.


We all naturally resort to automated emails / automation to scale our marketing efforts. As a matter of fact, 55% of companies are currently using marketing automation. And why not? After an upfront investment in time and effort, automated emails allow store owners to keep shoppers coming back. Automated emails can be used to build awareness, cross-sell, and recover abandoned carts. Many studies have been conducted on the use and performance of automated emails. We know that you can expect 13% open rates, 6% click-through rates and that for every $1 spent, email marketing generates $44 in ROI.


But our real-life experience was not exactly that simple. As you devise your automated email strategy or re-visit your existing automated sequences, watch out for these 10 'gotchas'.  

1. Personalization means going deeper than first name/last name

We all know using dynamic tags into the subject line or email’s body is the first level of personalization. It definitely works and you should do it. But if you’re not careful, it can turn out to be a disaster:

  • Using dynamic tags, like {FirstName} or {CompanyName}, that don’t actually pull in your first name or company name  
  • Sending the wrong country information
  • Sending emails at the wrong time, to the wrong person

While there may be best practices to avoid such errors, addressing personalization means going beyond just first name/last name. By switching the way consumers see your brand, from providing them with experiences rather than just sales, offers or one-time deals, they will start looking at your brand as an experience and not just another place to waste money. It takes more than a good sale to bring a customer to your door. 

How to get personalization right according to our experts 

Give your brand human traits

Think of your brand as a person. This is why celebrity brands, if they’re done right, work so well. Look at brands as people in a way that they engage with them, how it hits them psychologically. What would that person say, what would that person do? How would they act? What do your customers aspire to be when they buy your product? Every product or service is bought through aspiration. Why do I buy your products? What am I aspiring to be? How can you be that and show me that I can aspire to be you by buying your products or services? That person that you develop is the brand.


Find the right voice/emotional connection 

Lisa Oberst: Customization is huge. We put a lot of time and effort into studying the audience, defining the brand voice, understanding the messages that will resonate with subscribers. The best campaigns resonate with readers and create an emotional connection because we put in the time to think of what the reader wants to hear. 

Adjust the message based on past actions

I’m a big believer in data and leveraging data to personalize those experiences. When you go shopping whether it’s in store or online, you’re basically voting. 'I like this', if you make a purchase or if you don’t buy something you say ‘I don’t like this’. For me it’s all about how do you get that relevant data into a digestible format so that you can then personalize the experience.


2. Decreasing engagement rates & deliverability issues

This goes hand in hand with personalization. Because everyone does the same thing, people are email fatigued due to so many emails they receive and don’t have the time to engage with them. Try subscribing to 10 different stores’ newsletters and you’ll get overwhelmed in the first couple of weeks too. 

Too many emails can burn out your subscribers. Too few emails could result in lower sales. So how do you maximize deliverability? 

A quick and easy way to increase deliverability and reduce spam complaints is using your brand’s name in your “from” line. It’s also been proven to improve open rates. People crave human connection, thus more and more companies choose to use a front person, an individual, to drive up their email marketing. Give your emails a personal touch by using something like "Emma from Brand.com".

Another issue that hurts deliverability is forgetting to get rid of your inactive subscribers. You know what they say: it’s better to have a few real friends than a thousand fake ones. Same goes with your subscribers. Quantity does not equal value. Make sure you keep the unsubscribe or update preferences options visible. 

Ideally, your subscribers won't need to look for the unsubscribe button in the first place. Our experts weighed in how to keep your email list subscribed and engaged.

Optimizing the entire customer lifecycle

Dean Dutro: The full customer lifecycle, online and offline. For traditional marketing you’re looking at the awareness stage, what competitors look like. We’re actually working before the existing list. I like to view it from a lifecycle perspective. Prospect, new customer, repeat customer, vip customer, brand loyalty, lapsed customer, lapsed prospect. For each of those stages you want to have some sort of touchpoint. By having these touchpoints you can move them from one stage to another quicker. Building the relationship doesn’t have to be hard, it’s really about how many touchpoints can you get in, what messages are you creating for those touchpoints and sending them at the right time. Our entire strategy is built around the customer lifecycle. 

Getting away from the hard sale

William Lynch: The hardest part of email marketing is getting that initial subscription. There are numerous brands that are consistently doing hard/spam sales. Show trust and relevancy through the quality of your content to grow an audience, this will yield greater results in the long-term.

Setting prior customer expectations

Rishi Sharma: The thing that works the best for us is sending content on a regular basis and occasionally when customers receive a promotional email, they will be more receptive of that. With each of the emails we send out, we set customer expectations prior to opening them by using emojis for each piece of content. For example, the microphone emoji for podcast-related emails, the shopping bag emoji for promotional emails and so on. 

Focusing on your product

Erik Huberman: Number one is a good product. How many people are starting things like their next business idea like their dropship company and they're gonna go pick some random items from China and create a business around it. It’s not how it works. If I’m good at Facebook ads, I can market anything. No. If you have to buy every customer you sell, and they don’t like what they’re receiving you’re going to have a very short lived company. Good product, good service is part of marketing. If you’re not a master of your product, you’re gonna get in trouble. 
Adena Merabi: If you’re a business starting out and want to be successful online you have to make sure you have a product differentiator. Customers now are young, savvy, they want to relate with your brand, they’re not going to buy just because you’re cheaper. Definitely having a good brand story, product differentiators, a really good marketing strategy and also a good tech stack: having a reviews platform, a good eCommerce platform, a good SMS and ESP, making sure you have a good customer service platform, good shipping and returns process. Making sure that everything is seamless. Making sure that your creative is optimized, your marketing strategy is cohesive and omnichannel. 

Speaking to the actual objections first

Dean Dutro: Depending on where you are as a company, you’re either gonna know or not know. You may know that price point may be the purchase objection, or maybe it’s social proof or maybe shipping times. Let’s say you have a prospect. Why would they choose you over another company? You start to tailor your messaging, let’s say your welcome flow, for example, where you wanna have 10-15 emails in that flow where each email you can target a specific objection over time. Maybe you send them reviews, best products, comparison of other products. You can incorporate incentivising there as well. You don’t want to incentivise from the start, you want to speak to the actual objection first


3. Lack of human touch 

If we take Social Media, for example, the human touch there is irreplaceable. Most of the brands start off by building their community manually on channels like Instagram and Facebook. Why? Because they know it’s a long-term benefit to the brand. There’s no better way to get to know your customers and improve your brand than going straight to the source: them. 


The 3 pillars of marketing

Erik Huberman: Marketing isn’t just about advertising. A lot of people think that if you run Facebook Ads and people see your product they just buy it. It’s just not how it works. We talk about the 3 pillars of marketing: awareness, nurturing and trust. Good marketers know that it takes all these moving parts to create a successful marketing campaign. Bad marketers spend time on Facebook Ads all day.

The way to build a brand is through trust and relationships

A lot of people focus on the acquisition side of things and conversion rates and they don’t really focus much on the relationship building side of things, which is actually when you start to generate profit.


Rishi Sharma: Up until now it’s been organic, building the brand and the trust. Our main pillars are around audience building. We have a podcast recently launched in March, a weekly newsletter, skin care content around the web. We have 2 blog posts every week focused on skin issues and skin questions. This content drives SEO value as well. We’re trying to provide as much value as possible.

Ecommerce is very much the same as face to face selling. You need to build that trust and relationship.



Put yourself in the customer’s shoes

Ryan McGuire: What I typically would tell people is to put themselves in the shoes of the customers and what is most important to a customer. The place where everybody can play. Whether you’re the retailer selling products, whether you’re the manufacturer, whether you’re the consumer, the agency or strategic partner. The commonality between all of that is the customer. What does the customer want? Are we fulfilling their needs and desires and if you are thinking about it from that lens it really sets up your entire strategy. If you’re all connecting with the customer and thinking about it from that perspective. 
Daniel Johnson: The customers enjoy being spoken to like a human being


4. Automations still need to be regularly maintained 

Automated emails are not just set it and forget it, you always need to be aware of what will be sent, when and why. 

In a recent survey conducted by me on a couple of industry-specific communities, I found that one of the biggest challenges marketers encounter is remembering to go back to older campaigns to refresh them.

“We get into production mode sometimes and forget to go back to test and improve campaigns that are already running.”

I like to call these email automation traps. Think of these traps as aspects of email marketing people usually overlook or view as huge challenges. 

The data trap

Ryan McGuire: The data trap. We either have not enough data in order to do it right or we have too much unorganized data that’s not useful. The resourcing trap or the ‘how hard can it be’ trap. I feel like there’s another trap: we're only gonna use the data we’re 100% confident it’s accurate. That limits people from using personalization.  

The creative trap

Erik Huberman: Creative is a problem, content. If you’re a new business it’s hard to create a compelling video, some really good creative. Getting attention it’s also a tough part of this. Again, if you’re having a good product a lot of time it will speak for itself and word of mouth is the biggest driver of business

The quick, small wins trap

Lisa Oberst: It's very important for brands to think long term for their list. If they only focus on immediate wins and bombard their list with scrappy sales emails, they will come to regret it in the future. We stress the value of quality content because once you've exhausted your list, it's very difficult to recover credibility within inboxes. 

The noisy clutter trap

Companies read a lot about marketing automation and they tend to be perfectionists too early. I wouldn’t focus too much on perfection when starting. I would just try to take your best-educated guess. Great requires data & optimization which takes time. I would also say keep your emails simple. A lot of companies are not user experience-focused enough. I would recommend having a singular goal with emails. Being more simple and clear with emails is a good first step for companies.


The budget trap

Adena Merabi: Underspending. If you don’t spend enough money, you don’t have enough wiggle room to test. Especially if you’re a new brand when you don’t have enough data. 

The overlap trap

Dejan Georgiev: Make sure to have a clear picture of all your automated emails. Drafting a flow map is the best way to see the full customer journey. Make sure no automated emails overlap or are sent within a short time span. Ensure you have all the necessary filters to avoid sending emails to people that shouldn't receive them in the first place. And, as mentioned before, don’t spend too much time trying to develop the perfect automated email and waste precious time having it up and running.


5. The fear of sending too many emails

How do you know when too much is too much? How do you know when diminishing returns start? Some say, the more emails you send the less efficient they’re going to be. Some say that the more emails you send, the more unique number of people will open them. Finding the sweet spot can be a struggle.  

Send content that customers need and want to hear about

Dean Dutro: Let’s say someone just purchased from you, what do they wanna hear about? A lot of people have this fear of sending too many emails right after someone purchased, when the reality is they actually want to hear from you more. They wanna know, when is the product going to arrive, did they actually receive the order, how do they use the product. Improve your communication in terms of customer experience through your own marketing channels.

Develop relevant content for future opportunities

Past behaviour and knowing at what stage of the purchase funnel the customer is will help you develop relevant content. A subscriber who abandons the checkout is much closer to making a purchase compared to someone just browsing products. The post-purchase relationship offers opportunities too. We usually thank customers for their purchase and use the opportunity for an up-sell or a cross-sell.


Stop focusing on the short term conversion 

The main thing is to meet the consumer where they are. How do I build trust for long-term? I’m not looking to get the short term conversion. My main goal especially launching a new brand is a positive interaction with customers and this way they are most likely to spread the message to their friends and family. That word of mouth is what makes brands scale.



6. Lack of customer feedback 

Automation flows are only as strong as the data. How do you know what is going to work and what will get the best results if you’re not talking to your customers? When asked, what are some of the best practices before setting up and implementing a successful email automation campaign, customer research was the first thing that came to mind.    

Start from the user and the problem you’re solving

The main issue is the lack of customer research. Not just research but understanding the user, understanding the problem you’re solving for your customer and how that applies to your business. I’ve seen that by working with companies that were sending millions of emails a day and they set it up based on a blog they read in 2016. The basics do work but you’re missing out. Start from the user, identify the problem you’re solving for them and understand how email works into the bigger picture and the story of your relationship with you and your customer because you shouldn’t just do something because people do it. And I feel like email automation is something that people just do cause they’re like ‘yeah we should do this’.


Map the email journey by understanding customer behaviour

Dejan Georgiev: You need to understand customer behaviour. What is the checkout completion rate, how much of the traffic happens on the individual product pages versus the category pages, etc. Once you have a grasp on the customer behaviour, you can start planning the customer journey and map out your automated emails.

Understand the essence of the product

Aristide Basque: The first thing I do in my research is to look at landing pages of competitors to find the tagline of that company. It generally gives me an idea of why people buy from that company. Looking at competitors’ websites is a really good way of understanding the essence of the product or service and the brand. It also gives you a strong perspective of what differentiates them from the rest.

Reviews and user generated content can direct your strategy

Our team spends a lot of time during the initial discovery phase looking through user-generated content (including reviews), as well as questions the customer support team receives. This information will influence the strategy we tailor for each brand. The goal is to help customers shop by speaking their language and providing valuable information before they even have to ask for it.


Quantitative research vs qualitative research

Daniel Johnson: Both are important. What am I actually going to achieve with this research and get as close to the customers as I can. Surveys are super valuable in gaining massive insights but the best most valuable insight I found when I went to the public customer and I just talked to them about how they use our product, how they refer it to their friends. I personally find it very easy, because people like talking about themselves and if you make them feel special, they’ll sing. This is how I created one of my most successful ad campaigns.


7. It takes longer than you think

Either you do it yourself or your digital marketing agency, building an entire email automation strategy involves patience and quite some skills. You have to go through the research phase, plan accordingly, test to get an idea of what works best and iterate as you go. Our experts put a lot of time and effort into making sure the strategy is optimized for success and that’s exactly how you should think about it for long-term success.

Projects depend on budget and level of customization

Lisa Oberst: Because our team puts a lot of time and effort in customization, setting up a robust strategy usually takes no less than 3-4 months. Then, of course, you can continue to optimize, test, and improve.  
William Lynch: It depends on budget and what they’re trying to achieve. We put in place revenue and engagement goals and work up from there. 
Adena Merabi: It takes about 2-4 weeks to get their first campaign off the door. 
Aristide Basque: Generally, I’m doing it on the go. Usually it takes around 7 days and there’s an initial 1-2 weeks for creatives to be approved.  

Aim for constant optimization, not perfection

Dejan Georgiev: It can take anywhere between two days and a week to develop an email automation following best practices. Don't waste time developing the perfect email, you can always optimize later. Get your automated emails up and running as soon as possible so you don’t miss out on creating crucial engagement and revenue.


8. Emails are so predictable

This one really resonates with me. For example, when I get a transactional email, I can tell from the subject line that it's a marketing message so I mostly ignore such emails. 99% of the time, those emails are not meant to help me. They're sent to help the store. 

We’re approaching a critical threshold where the average person receives so many marketing emails a day that the efficacy of any single email is stunted. There’s no more surprise, there’s no “aha” moment, there’s nothing. At best you’re going to convert them with a discount.


Research helps you stand out from the crowd

Aristide Basque: Competitive research is really, really important. Looking at competitors is generally really good to help me understand the essence of a brand and why people buy from them. It tends to also allow me to understand why this company is different from the rest in a good way. Being unique and not copying others goes a long way online.

There’s a big misconceptions on what converts nowadays

Adena Merabi: There’s always been a misconception on what type of creative works. It depends per brand. But what we found, is that the type of creative that converts is the scrappy iPhone shot, user generated content. You don’t have to go out and spend millions of dollars on lifestyle, high quality shoots. It’s really the scrappy UGC that’s converting really well. You want it to feel like it’s your friend on Facebook posting the video. It doesn’t want to look like you’re looking at an ad. 
William Lynch: One of the biggest trust signals you can utilise is user generated content. Someone tags your brand in an Instagram post and then you can automatically ask them for marketing permission to use that. That goes into your library, your Facebook Ads, email marketing, product description pages to show social proof & trust signals to the next customer. It becomes a very effective & powerful feedback loop.

Best practices for setting up a successful email automation

Dejan Georgiev: Make sure you know your audience. Learn from their past behaviour, segment, and then send only the useful and relevant content. You don't want to be too intrusive with your automations, so establishing the right sending frequency is crucial. This is where A/B testing becomes your most trusted ally. Set up the triggers and filters for each automated email sequence and custom-tailor the content to match the behaviour that triggered the email. Do not create cluttered automated emails, keep things simple and to the point. If you are in doubt about how to enrich an email with content, testimonials and recommended product blocks are your best bet.

If you're still reading this article, by the end of it you’ll know exactly what needs to be improved on your existing automation programs and what to add next. All the things discussed so far can be overwhelming, that’s why I kept the best for last. The next 2 challenges will teach you how to go beyond just email automation and drive more growth by adopting an omnichannel approach. 

9. It’s a one-way communication channel 

Email in its essence is a 2-way communication channel. Email marketing though, is a one-way communication channel. You can’t really respond to an automated email. That creates a barrier between brands and consumers. 


Customers want to be heard and taken care of. They demand a customer-centric shopping experience—one tailored to their wants and needs as valued customers. As a price to their loyalty, they seek brands which deliver personalized, targeted messages across all channels.

Listen and reply to your customer

Ryan McGuire: I think the best marketers out there have cracked the nut on 2-way communication. I personally don’t like when I engage with companies and it’s only 1-way communication. To me that basically means the company is not listening. If somebody is sending me an email all the time and I’m never opening it, it’s going right into my spam folder and I’m just deleting it. They should be looking at that and say let’s try a different strategy for a while. I’m a big believer in 2-way communication.

2-Way communication builds great customer support

Dean Dutro: Marketing serves several purposes: as a profit tool and as a customer experience tool to build loyalty. Flows and automation are very popular because they’re effective but they’re only one piece of the puzzle. You can only do so much with those. You can’t always update them as fast as you can send out a new message. Your flows are going to be very timing message based, your campaigns are gonna be more context message based. 


10. The fear of going beyond emails

Email is definitely great and not going anywhere. However, the stats are making a statement. For example, some markets and demographics prefer SMS marketing due to its 98% open rates, 45% click-through rates and 6-8x times higher engagement rates than email. Also, 90% of SMS messages are read within 3 minutes, but takes 90 minutes or more to respond to an email. 


Extending beyond email marketing on channels like text messaging while creating an omnichannel experience which customers will love was one of the most discussed topics during these interviews. 


True marketing automation goes way beyond emails. 


It’s not SMS or email, it’s SMS and email.

Dean Dutro: A lot of people view SMS and email as battling each other for who gets the attention first. Do we ask for an email or do we ask for a phone number? Our response is to ask for both. If they are coming from a phone, you should ask for their phone number. If they are coming from a computer, ask for their email. 

PRO TIP: One thing to do is embed in your flows specific emails requesting people to enter their phone numbers. Because people are more inclined to answer their emails.

Adoption of mobile commerce is increasing

Dean Dutro: Now in 2020, more people are shopping on their phones than on computers. That being said, how do we tailor our messages to look good when they receive it on their phones? That comes down to timing. If you can contact the customer at the right time, that’s gonna count for like 80% of your success. Then if you have the right content at the right time, that’s gonna launch you further.
Erik Huberman: SMS is crushing it. Email marketing hasn’t gotten any better or any worse and it’s always been a very big part of online marketing. For email marketing the average open rate is 15% and the average click-through rate is 3%, for SMS the average open rate is 98% SMS and the average click-through rate, 30%. It’s drastically better. It’s a little harder to collect a phone number but not much and people are getting used to it pretty fast. It’s an adoption curve but everyone who’s adopting it has been doing very well. 
Ryan McGuire: For me, SMS is a perfect channel to engage with consumers in today’s day and age. Cuts through the clutter. The open rates are much much higher. It’s got this weird balance between immediate and not immediate. There’s not this expectation you have to respond immediately. Whereas if you think about how consumers are engaging with virtual chat it needs to happen in real time. Text can happen a little bit in a slower time. SMS is a very strong complementary channel to the other channels like direct mail and email where you can do some holistic communication and shortening of that message and use SMS to build on an email campaign. 

Adoption of omnichannel strategies

The more data you have, the more you can get targeted with your audience and acquire more customers. I think brands are afraid to explore new channels, they want to stick to Facebook or Google, they want to keep their email marketing in house and outsource other channels. It’s really important to have an omnichannel strategy because the more you can have a cohesive strategy the more data you can collect and what your audience looks like and what your customers look like. If you are doing email, SMS, Facebook and Google, you want to make sure every channel is speaking to one another. If you’re putting out a campaign on Facebook, you want to make sure someone clicks through, they get retargeted with another ad on Google or Youtube and then targeted with an email, then with an SMS. Don’t be afraid to explore channels.


Key takeaways

Emails have been here for decades and they are here to stay. The reason I decided to write this article is to put all these insights into one place and show that email automation is not a silver bullet. With that being said, email is here to stay, continuing to be a high growth channel for most eCommerce brands but starting with this year, brands should adopt an omnichannel approach and explore more channels like text messaging. 

If you’ve ever dealt with any of these email automation struggles or faced different ones, I’d love to hear about it. 

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Lisa Popovici

Co-founder at Cartloop. Med School graduate turned to tech. When she's not working on growing Cartloop, you'll probably find Lisa working out or preparing an avocado toast for a late brunch.

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