Think about Your First Email like You Would Your First Handshake or Eye Contact

Think about Your First Email like You Would Your First Handshake or Eye Contact

If you were to meet your customers in real life, how important is that first greeting, that first handshake, that first eye contact? Is talking about your company important? Yes! That’s why that first email matters.


At mailfloss we’re focused on helping email marketers get the most from their email marketing campaigns. We do this in a few different ways. First, we help email marketers improve their deliverability through the use of our email list verification tool. Secondly, we work hard to educate email marketers on the various topics relating to running a successful email marketing campaign.

Today, mailfloss had the opportunity to chat with Ryan Phelan, the co-founder of the email marketing agency Origin Email. Ryan has two decades of experience working within the world of email marketing, so we’re excited to have him with us today to share his insights with us.

So without further ado, let’s jump into the discussion.

The Interview

Hi Ryan and thank you for joining us today to talk about your involvement in the email marketing space. You have almost two decades of experience in this niche! Let’s jump in and have you tell us what drew you specifically towards email as a marketing channel early on in your career? 

I’ve been in email marketing for more than 20 years. I started off in the digital space running affiliate and email marketing programs for a start-up business in Omaha, and I ran email on an app on my computer. Ah, the good old days!

What drove me to concentrate on email marketing was that it showed more promise than affiliate marketing, even in those early days. It wasn’t just the free flow of information in that first era of email. It was that the innovation arc for email is very long. The up side for me was the ability to get messages into the user’s inbox at their invitation, to see our messages in the same place as valued personal email.

I loved the flexibility of email and what email could do. The pace of innovation is changing email, but email is also changing and accelerating the pace of innovation. Try to find a mobile app that doesn’t have email as the primary or secondary connection to the user.

Well, that and the huge mROI keep me in email!

You also run Origin Email Agency, which is an agency that helps mid-market and enterprise companies with email marketing. You help with overarching strategies, comprehensive modeling and segmentation to name only a few services. Let’s start with strategy. What are the biggest mistakes you see email marketers make when it comes to email marketing strategy? How can they overcome these mistakes? 

The biggest mistake is that email marketers don’t spend enough time on strategy. Marketers focus too much on tactics. They don’t take a step back and look at why someone reads their emails instead of how they read them. From promotional to triggered emails, from welcome messages to cart abandonment, any kind of email message you can think needs to have a strategy, a “why” behind it.

That’s the theme I see at company after company that I’ve worked with. The first thing I do when I start working with a new company is to ask them about their email strategy and then wait for the crickets while they try to come up with something.

After that, I dive into helping them create a strategy, and that defines the path forward in their program. I can teach them about strategy, walk them through a strategic brief and help them understand why it’s different from a creative brief. I’ve learned that when people are trained properly, they can do a strategy session in 30 minutes and end up saving time down the road.

Let’s talk a little about overarching strategy and strategy design. Now a lot of small teams have a challenging time putting together a month’s worth of email content. How do small business entrepreneurs balance the need for an overarching email strategy while working within the confines limited resources? 

These claims about limited resources – they’re just excuses for not doing the work. Every business owner has a business plan that took time to create because it’s important to the success of the business. Entrepreneurs who say they don’t have time to map out email strategy are missing the boat, and I question their leadership abilities.

You don’t have to plan out a strategy a year in advance, or even a month. That can be a monumental goal for some people. Maybe you plan on Friday for the week ahead. You don’t have to map out each point in your strategy either. Take the time to figure out the general themes and direction, and then fill in the details as the campaign gets closer.

You can always change your direction. Just don’t make up excuses about why you can’t do it.

Can you tell us a little bit more about what “modeling” is and how email marketers should approach their own email modeling strategies? What are some techniques you’ve seen successfully used when it comes to email modeling? 

Modeling is something everybody should be doing. It’s an upgrade from segmentation. Here’s how it fits in:

  • Batch-and-blast is one email to everybody on your list.
  • Segmentation is differentiating among groups based on one customer variable.
  • Modeling brings in other pieces of data that paint a picture of your customers, and you use it to enhance your targeting. It uses groups of like characteristics to predict behavior.

Modeling is a great technique for companies with large amounts of data and data scientists to come up with formulas for creating useful buckets of customers. With modeling, you can run it against new customer behavior and then run it again to look for changes in behavior. Customer behavior changes all the time. As a customer, just because I have an interaction at one point in time with a brand, but I’m not that same customer for all eternity.

Models can help you find the most common and lucrative groups of people and present them for unique marketing opportunities. Then you come back for a strategy to market to these groups that meets their needs.

These can be basic, like purchasing, or attitudinal, or incorporating various third-party data that shows interests, browse behavior on other sites, preferences for things like sports and hobbies and spending patterns.

A model by definition does not have to be vast in its inclusion of data. You can build a model on a couple of data types and use it to say, “This is the type of people I’m looking for.” From that, the goal is to predict action and mirror your marketing to support that prediction.

In your experience what are some of the most overlooked marketing automation systems that companies fail to put in place early on? In your experience, which of these automation systems end up having the biggest impact on the bottom line? 

Companies generally send a comparatively small number of emails in automations, like order and ship confirmations, welcome emails, behavioral triggers and indicators of interest.

These numbers might be small, but they add up to 50% or more of ecommerce revenue. That’s because one thing that doesn’t change about email is that relevance is king. If you send relevant info, whether to B2B or B2C users, they’ll convert.

Marketing automation looks for micro-moments of customer intent and serves up messaging around them. Suppose I buy a new washer and dryer but not the pedestals that most people buy. A marketing automation will wait seven days and then send me an email suggesting I buy those pedestals because I might already be tired of leaning down to put laundry in or take it out.

Marketing automation recognizes that micro-moment and sends me a message that supports it. And it usually pays off.

You have to find your micro-moments and serve them with appropriate emails. It could be an abandoned cart reminder or a next-logical product or something else. The problem is that many people ignore these messages because they take time to set up, or they don’t want to analyze the data that tells them what kinds of messages to create.

The other issue with marketing automation is that people let their messages get outdated because they aren’t looking at them every day or testing them for success.

If you do go back and check on your automated messages, you could find it’s time to change things up. One client moved an abandoned-cart email back by one week. That change took 5 seconds to make but it boosted their conversion rate.

If you were to walk into a small bootstrapped startup today and take control of their marketing for the day, what three things would you do (or systems would you put in place), to help with sales? 

Well, first, I would need a 12-hour day. But I could make it work.

For the first couple of hours, I would learn everything I could about the company: its programs, offers, sales, customer service and customer types. I wouldn’t just talk to the executives; I’d go visit the front-line employees. I would want to learn the big motivators, the reason to believe in that brand.

Next, I would spend a couple hours working up a marketing strategy, looking for efficiencies, opportunities and directions and prioritizing them. Do we need to create marketing automations? Bring the website up to date? What’s the low-hanging fruit that will get us big wins right away? After that we can look at projects that will take longer to execute on.

Finally, I would spend the rest of my day writing strategy briefs, reviewing copy, teaching marketing strategy and making sure the marketing team is aligned on our goals.

One thing I would not do: Come in with a silver-bullet plan that will fix everything all at once. That doesn’t exist. You have to put in the hours and do the work.

Let’s talk a little bit more about email sequencing. What advice would you give to a company who is just starting their email campaign regarding the spacing of their sales focused emails? For example, should companies send two, three or five value focused email first before sending a sales focused email? How do you approach this ratio? 

My answer to any question on frequency or timing is this: What does your end user want to see? You have to define who your end users are and create messaging that makes sense to them. Should you send one welcome email, or two? Three? 10? There’s no single standard or right answer.

Think about what your end user wants, and deliver on that.

I’ve talked a lot about the self-justification of email messaging. Does your end user really want to see that message, or are you sending email just to send an email? Often you’ll find the answer in testing. Test different series, different numbers and timing. The answers can depend on whether you’re a new or established company.

That’s why I’m not going to say that you must send your abandoned-cart reminders at 24 hours, one day and three days after abandonment. Those are starting points. They’ll be different for each company. So you start, and then you test. To develop a good abandoned-cart program you might have to spend six months planning it, testing all the variables and then fine-tuning it.

Tell us a little bit more about some of the best first emails that a company can send out. Why is the first email so important? 

To answer this question, I’ll ask another one: If you were to meet your customers in real life, how important is that first greeting, that first handshake, that first eye contact? Is talking about your company important? Yes! That’s why that first email matters.

Your welcome email sets the relationship. It tells your end users who you are and what they can expect from your emails. Don’t drone on about yourself forever; make it short, sweet and to the point. If you can’t sum up your company in three bullet points you need to rethink it!

Lastly, if you were tasked with growing the email list of a bootstrapped company from 100 to 1000, what are three strategies you would use to help you achieve that goal without breaking the bank? 

None of these will be easy to do. So, relax and enjoy slow growth to 1000.

First: Look at every prospect or subscriber touch point and have lead collection there for your email program. A lot of companies miss this basic step to capture people’s information.

Next: Look at your email communications and be sure you are delivering value to your end users.

Finally: Look at your opt outs. How many subscribers have stopped interacting with you? Plug those holes. Make sure you are not losing people for no apparent reason. It’s easier to keep them than to replace them and then acquire more to keep growing. Acquisition is about quality,

Thank you greatly for taking the time to chat with mailfloss’s email marketing blog readers today Ted. This has been a really insightful interview. To our audience, if you’d like to learn more about Ryan and the work he does, you can follow him on Twitter or head over to his website here.