9 Favorite Lessons From 20 Years in the Email Marketing Industry



There are a lot of disadvantages to getting older but there are also some benefits such as cumulative lifelong learning and the experience that comes with age. In my final article for Webbula, I thought I would share several lessons, learnings, observations, or tips from more than 20 years in the email marketing industry.

Following are 9 lessons, most of which you’ll see have a theme of math:

  1. It’s all about the math. Email marketing is all about math. That’s it. Regardless of your role in the email marketing ecosystem, if you’re not making your decisions based on serious analysis and math (or maths as the Brits say), then you probably are making the wrong decisions.

Takeaway: Learn to love Excel.


  1. Always be testing. One of the earliest lessons I learned was way back in 2002 and it proved my first point and set the tone for the rest of my career. I was deploying the email marketing program for a multi-channel outdoor sports equipment retailer. They were using subject lines that always included multiple product brands that reflected the inclusion of typically about 10 products in each email. I didn’t think it was the optimum approach and they allowed me to do some split tests of the subject line several times.

I tested subject lines that were focused on just a single brand and product in the email. The client was nervous and concerned of course as they were afraid that the singular focus would slight some of the brands and products included in email. 

What resulted was that my focused subject lines had lower open rates but produced significantly higher revenue. Fewer people were prompted to open the emails with the focused subject lines, but those that did were much more likely to purchase the product highlighted in the subject line. 

Takeaway: The lesson isn’t that narrowly-focused subject lines produce more revenue than broad subject lines (your results may differ), but rather to improve your results you always have to be testing. One client initiated “Testing Tuesday” where the marketing director required each of his team members to test something every week and then report the learnings in their Tuesday team meeting.

  1. The power of triggered messages. Every email marketer knows that messages triggered by some subscriber action, lack of action, or data points can produce huge positive results. Many marketers, however, put off setting up multiple triggered/automated email messages because at times they can be complicated to set up and/or maintain. But not adding more triggered messages means you are leaving huge money on the table.

One e-commerce client I worked with had set up about 15 triggered messages which accounted for 10% of their annual email send volume — but 40% of the company’s revenue from email. 

Takeaway: Establish a goal of setting up one new triggered message each month — after 12 months you will be printing cash.


  1. Make it easy for subscribers to do what they want. Whether it’s unsubscribing, changing their email address, making a purchase, or trying to understand a discount offer or shipping options - your job is to make it as simple as possible for your subscribers. 

One of my favorite approaches over the years is providing a table of shipping options, deadline dates, and costs in your holiday season emails. The first client I saw use this practice was King Arthur Baking (then King Arthur Flour) back around 2009.


A second favorite is to remove any need for your subscribers to do math and calculate  all aspects of a discount offer for them. This includes the original price of the product, the percentage of dollar savings, the actual dollar amount of savings, and the new discounted price.

Takeaway: Your subscribers are busy, likely checking your email on their smartphone — perhaps even while walking. Part of your job as an email marketer is to ensure there is as little friction in their purchase process as possible. Make it easy for ‘em.

  1. Be prepared for the inevitable mistakes. If you are an email marketer it’s only a matter of time before you’ll have a mistake in one of your emails or perhaps an issue on your website, mobile app, or landing page related to an email campaign. One of my retail clients would send a weekly promotional email on Sunday morning and this time the price on a product was different in the email than what it was on the website. Ugh.

The client asked what they should do and I advised sending an “oops” correction email to the subscribers who clicked on the link for the product with the wrong price and adding a slight additional discount as an apology offer. (Note: This was a motorcycle parts and accessories ecommerce company and so I had some fun with the subject line by adding the phrase “Road Rash.”)

The conversion rate on the “oops” email was an off-the-charts 40% versus their normal 3%-4% and generated substantial additional revenue.

Takeaway: The real takeaway here is to always be monitoring your email program looking for aberrations or issues and be prepared to quickly take action. You should also have an email corrections process mapped out so when the inevitable does happen, everyone in your company knows exactly what the next steps are.

  1. Go counter to conventional wisdom. One of the lessons that I “stole” from my friend Dela Quist of Alchemy Worx and is now part of my “thinking DNA” is to not follow the herd and go against conventional wisdom. A simple example is the previous lesson on corrections emails where after sharing the story with Dela years ago his response was rather than send the “oops” email to just those that clicked the link, send it to the entire database.

In this case my client wasn’t comfortable sending another email to the entire database, but if we had followed Dela’s advice, the company likely would have generated significantly more revenue from the corrections email. In essence it would’ve been a corrected “resend” — just under the guise of the actual mistake.


Takeaway: When most of the experts say one thing, it might be the correct approach. But don’t just accept it, try something counter and see if it works even better for your company.

  1. Want additional budget and resources? Prove it. A client wanted to build a sophisticated, multi-email cart abandonment email marketing program, but didn’t have the necessary budget and resources. This marketing executive built a financial model that showed what the return on investment would be for a simple phase 1 approach using conservative assumptions. 

He sold the CFO on the budget for that initial phase, then launched the program and proved the ROI. With those results in hand, he obtained the needed budget and resources to deploy the more complex second and third phases. 

Takeaway: The best way to obtain the budget and resources you want and need is to promise a stellar ROI, then prove it incrementally until you get the full level needed to crush it.

  1. Go beyond the inbox. Abandoned shopping cart re-marketing emails are popular because they remind a shopper who showed purchase intent to go back and complete their purchase. But cart remarketing emails are a bit like “shooting fish in a barrel.” 

It is actually much harder to work with other departments to solve the problem and minimize the issues that may have caused the abandonment on your website. Great email marketers don’t just focus on what happens inside their email but rather on improving the entire purchase experience for the subscribers in order to achieve the end goal for them and your company.

Takeaway: Identify one of your company’s biggest goals or challenges and see how you can design your email and related programs to help solve it. You won’t just be an email marketing rock star, but a customer experience rock star!

  1. The answer is right in front of you — sometimes you just need a little nudge. I was wrapping up a 4-hour eCommerce email-marketing best practices and brainstorm session and I could tell my clients in the room were exhausted and overwhelmed with ideas. One of the marketers, her head full of a dozen different ideas to pursue, asked me: “Where do we start?”

“You know,” I responded to her and her peers. After several seconds of silence, everyone in the room smiled and nodded as they realized they knew the answer. This client had a free shipping program similar to Amazon Prime. Their “Gold” program costs $49 per year and offered free shipping, advance early notification of special sales, and several other benefits. 

I’m forgetting the exact percentage now, but it was something like 70% of their annual revenue came from customers who were members of the Gold program. But they weren’t growing the net number of Gold program members as a significant percentage of existing members didn’t renew their membership and they also weren’t acquiring enough new members to the program.

On my flight home I received an email from the VP of Ecommerce who had spent the next few hours after the meeting mapping out multiple series of automated messages to address both the acquisition and retention of Gold members.

Takeaway: In the last 20 years I have rarely met a client that didn’t intuitively know what they needed to do to take their email marketing program to the next level. They just needed a little coaching and coaxing to help management see the light.

If you are an email marketer you already know how amazing the channel is. My parting advice is to “think beyond the inbox,” think big, think counter to prevailing wisdom, always be testing, and focus on the “maths.”

Good luck and long live email marketing!


Loren McDonald
CEO EVAdoption

Loren consults with companies to maximize revenue, leads, and customer retention through content marketing programs including webinars, thought leadership/research and email marketing. He has 36 years of experience as a consultant, marketing executive and thought leader at companies including IBM, Silverpop, Acoustic, Arthur Andersen, USWeb/CKS, EmailLabs, and Lyris.

He has written more than 500 articles, produced dozens of white papers and special reports, spoken at more than 350 conferences in 14 countries and presented on 200+ webinars. Loren has won multiple awards including 2005 Best Marketing Executive (American Business Awards - "Stevie's") and 2011 Email Marketer of the Year (Email Evolution Council).

Social Media:

Twitter: @LorenMcDonald

LinkedIn: https://www.linkedin.com/in/lorenmcdonald/

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