Ask the Experts: Can you share mistakes you made early in your career and the lessons you learned to help another email marketer?


In 2021, Webbula launched a video series where we sat down with email industry experts to discuss various topics within the email marketing world. Each month, Webbula introduced a new lineup of email experts with a new topic.

Follow along in 2022, for 12 new questions and a new lineup of email experts. Thank you to every email expert who participated in this video series and provided advice to other email marketers. 

Video transcription completed with Descript. 


HubSpot Video


Kristie Doak

Manager, Database Marketing, PGA Tour


"Certainly, we all make mistakes. I went on vacation and had someone else take over email. They knew the system. They probably didn't know the small ins and outs that I was aware. They actually sent an email with no footer, which meant no, legalese at the bottom of the email, which is a huge no-no.

Luckily this was quite some time ago. It was before GDPR and before email got super regulated, but it was a lesson for me to think about if someone's going to take my place. It's like that whole exercise of telling someone how to make a peanut butter sandwich. You have to tell them to open the bread wrapper and take the bread out. It helped me put together some step-by-step instructions in case I were out or in case someone new came along, something that I could just kind of hand to them and go with.

I've done the whole, I sent an email, but I only sent it to the seed list because I forgot to change the audience. I am now a humongous fan of double-checking, absolutely everything.

I've sent an email and assumed all the links were working, especially the ones that are repetitive and there all the time. I didn't test those and later come to find out they were not working like they were supposed to. Double-check your work, and if you're working for me, I'm the only one working on email campaigns, so it's very easy for me to read over a typo, or a punctuation error. I look at it all day, every day. Having a fresh set of eyes is good. There are times when my kids are here, and I'm like, "Hey, read this. Does it make sense"?

Find someone that can double-check behind you occasionally and just make sure you have things right. "



HubSpot Video


Betsy Grondy

Senior Email Marketing Manager, Blackhawk Network


"The first one, and I think anybody who does code is going to immediately recoil. The first lesson I learned in email marketing was, don't copy and paste from a Word doc. It will jack up your email. Just don't do that. Take it into a notepad, and strip all the formatting out.

That was one of my big mistakes. Another one was not double-checking lists. I did have an incident where I was like, "oh, this email is good to go. I'm going to send it." I sent it to the completely wrong audience. That's like the last thing I do before I hit send any time now is, 'is this list the right list? Okay, good. We will hit send.'"



HubSpot Video


Shmuel Herschberg

CMO, Shyn Media


"I've got two answers to this. I think the first one is going to disappoint some of the newbies on the block, but the second one, I think will be okay with. The first one is not having a rhythm. Especially if you're managing a bunch of campaigns from the segmentation, automation, and the actual newsletters. There's a lot going on and it can be confusing.

My advice is that if you are overwhelmed, relax, and know that this takes time to get into that rhythm.

The other thing, I think, is not testing your email. That can't be overstated enough. You have to test the email. I'm a big of having your own seed list or signing up for like Gmail, Yahoo, Hotmail, AOL, and any type of ISP that's in your database. Make sure you sign up for those emails and see them and actually send real tests. Not just the test features that a lot of email service providers offer, but actually set up a seed list and set up your campaigns before and really test before you start sending out tens and hundreds and thousands of campaigns. That could be very helpful to make sure that you're setting it up correctly.

When it comes to broadcast, so much of this depends on cloning old campaigns. If you're cloning the wrong thing, you're going to be, unfortunately, sending the wrong type of email out and we were trying to avoid that.

Make sure you test and get another set of eyes on those test emails to ensure that your emails are correct."




HubSpot Video


Jeanne Jennings

Founder, Email Optimization Shop, GM at Only Influencers, Chair of Email Innovations Summit


"I think looking back on the things I did that I consider mistakes, they can all kind of fall into one bucket for me, at least. Which was I made assumptions. I assumed things. So for instance, I assumed that email authentication was in place, because why wouldn't it be? Everybody knows you have to have DKIM, DMARC, and SPF in place, and yes, they were not in place. It never occurred to me that the IT people, and at that time I was on the brand side, were less knowledgeable about email than I was. So that was one of the big mistakes, assuming that authentication was in place.

The other mistake I made, as I assumed in a couple of jobs, and also a big thing with clients at first when I was a consultant, assuming that attribution was in place.

I can remember sending email campaigns and I've got the open and the click data there in the platform and I'd say, well, now we need to see the revenue in the sales that came from each of these two versions.

Either there was no way to tell what sales came from either of these versions, or you had a big group of sales that came from email that day, but they couldn't tell us which version it came from. It made the tests impossible to declare a winner.

I think assumptions are the biggest thing. The other thing, quite honestly, and I think this falls into this bucket, when I was younger, I assumed that people who are older than I am, knew more than I did. I assumed that the IT people knew more about email than I did.

I assume that the people I was reporting to you knew more about email than I did, and the truth was in most cases, that wasn't the case. That's something I would say to folks. Don't make assumptions about what other people know, and don't undervalue your own knowledge.

I assumed that everyone in the world had every piece of knowledge I had and every piece of knowledge they had. And I learned very quickly that wasn't the case. "




HubSpot Video


Andrew Kordek

VP of Customer Engagement, iPost


"Absolutely. First of all, when I started in this industry, I actually had hair. So if that's any indication of some of the lessons that I've learned over the years - no, but in all seriousness, I learned three valuable lessons through my mistakes. The first one was taking direction from people who thought they knew about email marketing. It's partly because they had an email address. In fact, almost everybody has an email address. And just because they had an email address, they had an opinion of how things should be done. So a mistake that I did was almost kind of listening to people and not really listening to what really was going on.

I think the second thing is that I wasn't testing early enough. We in an industry have been beating the testing drum for 15, 16, and 17 years.

Test. Test. Test.

I didn't get in and understand the value of testing until a few years in. So I made some mistakes because I went with my gut and didn't go with the data and didn't say, "Hey, I should do this."

The last thing I learned is that design, email design, email sending an email repeating of design and sending, I didn't do it for the subscriber, I did it for the marketer. I learned a valuable lesson and many different ways because it was the way to do it and the way we've always done it and we weren't really talking with the subscriber. "




HubSpot Video


Magan Le

Email, and Lifecycle Marketing, Bolt


"In my email marketing role at the beginning, I did a lot of copywriting, design direction, a little bit of coding, basically end-to-end email marketing. One of the things that I had struggled with was trying to get outside of my head because I was thinking very business-like. I need to write business talk. That was a mistake because the audience that we were serving, it was very conversational, and so it's hard for me to think it's okay to talk like me, which is kind of weird. I always feel like, as marketers, we get stuck in our businessy ways, and it's like, we are human.

Another thing would be, I feel like a lot of people make this mistake, is with merge tags, personalization tags, or whatever it's called in whatever system you're using. I've definitely made the first name mistake and some other word mistakes. Sometimes you could even have a mistake or it's not even that the merge tag is wrong, but the data is wrong, which is also terrifying.

Learning from that, always have someone else check your work, even when you are trying to push out this last-minute email right now. Take an extra five minutes. It's okay if it goes out five minutes later, have someone else check your work."




HubSpot Video


Dela Quist

CIO, Alchemy Worx


"The biggest mistake I ever made was sitting down and saying don't mail inactives. The reason I made that mistake was because I was following open rates. And if you go for open rates, then by definition, you want to send to only people that are very engaged with you, and that number, by definition, shrinks and shrinks and shrinks, right?

The people who engage don't grow over time and always shrinks. People die, get older, and grow out of using whatever your product is. There's a whole host of reasons why they might not need you anymore. If you're in retail or you're in any sort of business, the one thing you know, is that the number of people who buy so long as it's profitable, does that make sense? The better you are. The more people will buy, the better you are, and the better you do. And that's why I learned very quickly to start focusing on total opens rather than open rates. And it transformed the way I looked at the email and it got me a reputation where I'm introduced it shows, and it says, Dela Quist, the guy who says, send more email right.

A lot of people laugh at that. "That's Dela; he says send more emails if that's a stupid thing." But imagine if it was a TV conference, right. And I'm introduced at a TV conference, and it's Dela Quist head of the biggest TV advertising agency in the world. He's the guy that says do more advertising. Everyone would like go "yay, What a smart guy." But in email, they want to kill me because I just said the truth. That's the advice. The advice is that if you follow rates, you will do things that don't make sense when it comes to making money. And the only way you can comfort yourself is to talk about how good your open rates are.

And don't show the sales figures and say, sales are from sales guys, nothing to do with me and marketing. "




HubSpot Video


Naomi West

Senior Email & Lifecycle Marketer, Invoice2Go


"I wouldn't say these are necessarily mistakes, and they're more so just oversights on my part. The first is just a lack of understanding of the user life cycle. You go into email marketing trying to increase conversion or subscription of a product or purchase of a product, but you lack looking at what happens after they purchase.

Not putting myself in the shoes of my user was probably a big oversight when I started out with email marketing because there are so many different campaigns you can implement to create a better user experience overall.

The other oversight or small mistake when I started out with email marketing was not listening to feedback or attempting to find it from my email campaigns.

What are our users replying to emails with? Is it a broken link that you don't even get insight into? I've been at a company where I was a one lady show when it came to email, customer success, accounting, HR, all those things, so when I sent out emails, I was able to see the responses to them. As you grow in larger companies, you often don't get that. You don't get that relationship with your reply to, so putting in time with customer success to look at email trends and how people are interacting with your emails beyond just a click-through rate. I think was a big mistake when I started out."

If you enjoyed this post, be sure to look for future posts in this video series by signing up for our weekly newsletter!

Check back next month to listen to our next round of email experts' answers to, "Do you have anyone in the email industry who you consider a mentor? If so, who and why?"





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