Email Tales From the Trenches


Two savvy email marketers share some of the tips, tricks, and war stories that come with the territory.

I love email marketing. I really love email marketers. To generalize, they have thick skin, don’t get nearly as much credit as they should, and drive their business forward with crucial communications that can move the needle on key business goals. Two of my most popular columns ever in more than a decade of writing about email have been about and in celebration of email marketing pros.

This is an ode to them and I hope these honest stories from two email stars inspire you – or at least make you not feel alone as you are about to press the send button on that next campaign.

Heather Frank of insurance giant Aflac (disclosure: a BrightWave client) provided some really insightful and honest insight into what many email marketers may find to be similar on many fronts.


  1. During/After Deployment: Look at your reply inbox(es) daily and read a handful of replies — it serves as a barometer of subscriber sentiment on whether your content is resonating, and can key you in to unsubscribe, segmentation, or content issues. For high-visibility sends, check the inboxes within the first few minutes or hours, depending on how high-profile the send is . Your subscribers will sometimes be the first to tell you that a link is broken or the message is unclear, and I often get great (read: honest, brutally honest) feedback on how to improve the email based on the types of questions or comments I’m seeing.


  1. The time you don’t check something is the time when it will inevitably be wrong! This is obvious, but check everything before scheduling the send. Click every link, re-read the copy, check the subject line, from name/email and always click the unsubscribe, and sanity check the audience size. If your send is dynamically built or highly complex, check your highest-volume segments or enough segments to encompass the full range of content. For additional reassurance, skim through a handful of others, clicking the most prominent CTAs.
  2. Know that eventually in some way big or small, you are going to mess up an email send. Your goal should be when that day comes to curb the negative effects as much and as quickly as possible. Have an error email already approved and ready to go, as well as a templated status brief to provide to management (as these situations often demand frequent updates). This will save you time and allow you to better focus on the tasks at hand.

War Stories

  1. From past experience, one of our major email campaigns was built dynamically and took a large amount of lead time that kicked off early in the morning with a business-dependent send time. One day the program failed to kick off and the alerting process also failed, which meant we needed to hand-build the audience and hand-code the email in a very short amount of time to meet a set send deadline. Our email build specialist was in transit with a lengthy commute when the issue was discovered, so one of the email marketing managers who had a (slightly rusty) coding skillset jumped in to code, while I built the audiences. We both couldn’t leave our houses because of the time involved to do this, but somehow managed to get the emails out on time. It was an amazing day and we laughed about it later, but it pays to have that plan to the backup plan built in the case that Armageddon ever happens, you know what strategy to execute on. Make it a point to brainstorm those worst case situations and prepare.
  2. Sometimes you can get so close to a brand or have so many different tasks you are juggling that you miss obvious errors. This is inevitably the day that the CEO reads his email. It is easy on those days for impact to be exaggerated, and really helps to be prepared to use metrics to your advantage if you can. On the bright side, one of the great things about subject line mistakes is that they receive the highest opens! If you can tie that with increased conversion, it sure softens the blow.

Jessica DeLap, digital producer at Total Wine & More, a large and fast-growing national beverage retailer, shares some secrets, including the added pressure that comes along with sending alcohol-related content.


When my manager told me that we were now going to be responsible for sending our own emails, I was terrified. I thought of all the things that could go wrong. What if I sent the wrong email? What if I sent the right email to the incorrect people? This is a big one in my business, because we have a lot of legalities that differ by state, so a mistake could not only mean customer service complaints, it could mean legal issues!

I was nervous when I first started sending emails. I would set the email up to send, check it repeatedly to make sure that I had the right email and all links were correct. Then when the emails started coming in, I would check every link on them to assuage my worst fears. This led to a lot of wasted time. It’s something that gets better as you become more comfortable with the send button.


What makes it easier for me is that we have a few safeguards in place to ensure that mistakes don’t happen. We have someone else on the team check our email, because another set of eyes always helps. Our data has to be QA’d by our manager to ensure that we are indeed sending the email to the right people. We set up the email to send 15 minutes in advance and then check the pending sends to make sure everything is correct. When the email deploys successfully, and you see great open rates and revenue that makes the stress worth it.

Sometimes, despite our best efforts, mistakes do occur. There are different degrees of mistakes, with many requiring immediate attention. Depending on the mistake, you should ask your ESP to fix it (sometimes possible), contact your customer service department, and/or send a retraction email. Learn from it, move on, and don’t make the same mistake twice!