The Most Wonderful Time of the Year: Black Friday and Holiday Email Campaigns

The Most Wonderful Time of the Year for Holiday Email Marketing

Many retailers make 50-75% of their revenue in the last 2 weeks of November and first weeks of December. Email is the cornerstone marketing tool for retailers as they ramp up efforts to reach customer, gain new customers, and increase sales. Email Marketing guru Jeanne Jennings shares holiday email marketing practices along with a few tactics that might surprise you.

Tweak, Test, Refine.

Don’t wait until the end of the campaign to test and tweak your campaigns, says Jeanne. Test your campaigns early and use the results to send the best email to your list. You’ll see more conversions, revenue, and results when you test early and often.


[00:00:00] Jeanne Jennings: You know, the New York Times, if you want to get off their email list, they want you to get off their email list. They’re not going to try to trick you into staying on, but yeah, I think a lot of other brands out there don’t understand, you know, how damaging this is to your brand reputation. And honestly, it’s not even about CAN-SPAM or getting a fine from the government, it’s about what it’s doing to the relationship of trust with the people on your email list, who you’re trying to have a relationship with because relationships are what drives purchases. And this kind of stuff doesn’t lead to a good relationship. And not only are you going to have a bad experience, you’re going to tell your friends like me and everyone who is listening to the podcast about that bad experience.

[00:00:52] Bumper Intro-Outro: Welcome to Endless Coffee Cup, a regular discussion of marketing news, culture, and media for our complex digital lifestyle. Join Matt Bailey as he engages in conversation to find insights beyond the latest headlines, and deeper understanding for those involved in marketing. Grab a cup of coffee, have a seat, and thanks for joining.

[00:01:18] Matt Bailey: Well, hello, dear listener, and welcome to another edition of the Endless Coffee Cup. We’ve got a returning guest with us today, one of our more popular guests, Jeanne Jennings, the, can I say, Jeanne? The email guru. Uh, I, I love talking with Jeanne and I love talking to email. Jeanne, how are you doing today?

[00:01:39] Jeanne Jennings: Oh, my goodness. Well, after that lovely introduction, Matt, I’m blushing, but thank you. It’s, you know, it’s a pleasure to be here. It’s always fun talking with you and anytime I can talk email, I get excited about it. So, um, yeah. Thanks for inviting me today.

[00:01:50] Matt Bailey: Hey, you are very welcome. And you know what prompted this is I saw a post that you made about holiday emails and, uh, you know, of course I’m like it’s, well, when we started talking, it was October. I’m like, yes, we’ve got to talk holiday emails because it’s that time of the year where strangely enough, catalogs are showing up and the holiday emails are starting up and it’s, what better time to talk about this? And so, we’re going to get this wrapped up and produced as soon as possible because it is so relevant.

[00:02:23] Jeanne Jennings: That would be great, ’cause it is that time of year. I actually call this time of year, the Nods of Holiday.

[00:02:29] Matt Bailey: Oh.

[00:02:29] Jeanne Jennings: You’ve heard of the Ides of March.

[00:02:31] Matt Bailey: Oh yes.

[00:02:32] Jeanne Jennings: So, this is the Nods of Holiday, and the reason that is, is that the last two weeks in November, which is where I get the “N-O” in Nod, and the first week in December, which is where I get the “D” in Nod, um, for most companies, this is when they get about half of their revenue for the holiday season. Just in these 3 weeks.

[00:02:52] Matt Bailey: Wow.

[00:02:52] Jeanne Jennings: Which is a lot, if you think about it, because you know, for most of my clients, holiday starts in September. Some people start in August, but I like to start in September, and it goes through about the middle of December. So, that’s like 10 or 12 weeks.

[00:03:05] Matt Bailey: Wow.

[00:03:06] Jeanne Jennings: So, to think about the fact that, you know, for instance, the client I worked with last year in these 3 weeks we generated 45% of total campaign revenue and 40% of the sales.

[00:03:17] Matt Bailey: That’s amazing. That is amazing. Gearing up for that short amount of time, that’s unreal. Let me ask, when does the planning start for that campaign?

[00:03:28] Jeanne Jennings: Well, you really want to think about holiday overall. So, really you should start your holiday planning while it’s still really hot out and you’re spending your weekends at the pool. Like June, July-ish.

[00:03:40] Matt Bailey: Right.

[00:03:41] Jeanne Jennings: Um, that’s when you really want to start thinking about holiday. July, August, um, like I said, typically with my clients, we start in September, so if you’re not thinking of it by August 1st, you’re probably a little bit late with how normal production schedules go, 6 to 8 weeks, and you want to have time to do all the analysis.

Whenever I work with a new client, we always take a look at what they did last year to identify what worked, what didn’t work, what things we want to continue, what things we want to tweak, what things we want to test. So, there’s a lot of analysis that goes in before you’re even ready to write a creative brief for a specific email.

[00:04:14] Matt Bailey: Yeah. I, we used to joke, we would have clients or, or not clients, but, uh, potential clients call our agency around the September, October timeframe, looking for holiday help. And it got to be, our stock response was, “Oh, next year’s holidays?” Because yeah, everyone else is already in motion, and you’re trying to start way too late if you’re just thinking about it now.

[00:04:40] Jeanne Jennings: Exactly, and you know what the great thing about this time of year is this early November timeframe? If you’ve started holiday in September, you’ve got some learnings you can take a look at. When you do your plan, you want to plan for the whole holiday season. You don’t want to just plan for the first piece, but this early November time period, which is what we’re in as I’m speaking to you, is the perfect time to take a look at what you’ve done and then tweak going forward. Because even though you have a set plan, you want to make sure that you’re able to pivot, you want to make sure that if something’s working, you can do more of it, if something you thought would work isn’t working, that you can do less of it.

So, this is the perfect time, this early November timeframe, to reevaluate everything you’re doing. Not that you’re going to change your whole plan, but you’re going to tweak it. Like I said, especially for these Nods of Holiday, the last two weeks in November and the first week in December.

[00:05:25] Matt Bailey: Absolutely. Yeah. There’s, and it’s interesting because I’m starting to watch now who’s sending the emails and how often they’re coming. And I noticed there are some retailers, I only see their emails this time of the year. But yet, in, how I’m going to, I’m going to ask you, like, I’ve got you, I’ve got you for an hour. So, I’m asking you.

[00:05:50] Jeanne Jennings: I’m all yours, Matt.

[00:05:51] Matt Bailey: Yeah. Yeah.

[00:05:52] Jeanne Jennings: I’m all yours. Just don’t tell your wife.

[00:05:55] Matt Bailey: Well, here’s my question. Is that a bad thing? Because part of it, like I, one specific retailer, uh, it, it’s, they sell chess sets, which my daughter loves chess. She’s very good at it. I probably, I’ve probably gotten her 10 chess sets over the years, and I got that email and I said, “You know what? It makes sense to get this now, because the rest of the year, I’m not really thinking about it. And now it makes sense.” So, like just that one or two during these Nods, as you said, does that make sense or is it something that someone should be doing throughout the year?

[00:06:34] Jeanne Jennings: Actually, it totally makes sense. One thing that smart companies do during the holidays, is they go deeper into their subscriber file with their mailings. So, for instance, um, years ago, it was a long time ago, uh, I worked with Hasbro for a couple years. They were actually my first big name brand client, so I have a lot of love for Hasbro.

We had a bunch of people on the list that were inactive. They hadn’t clicked, they hadn’t opened in a while. And what we did when I started working with them, is we actually knocked back the frequency on those people because when we thought it through, it didn’t necessarily make sense to be bombarding them every month ’cause they just weren’t, didn’t seem to be interested.

[00:07:08] Matt Bailey: Right. Yeah.

[00:07:08] Jeanne Jennings: But if you’re a toy company, you have three, three big seasons. Pre-Christmas obviously, pre-holiday, uh, pre-summer, and pre-Easter. Those were like our three big times for sales. So, what we would do is those inactives, we would pull them out and dust them off during those, those big times, and we would start mailing them again. And we might mail them on the same frequency as the regular file during those periods, typically we mailed them a little less frequently than the rest of the file, and then we would watch. And if people came back to life, we would up the frequency, maybe put them into the active list, if not, they’d stay on the inactives.

But yeah, there’s a lot of people just like you with chess sets with other products, you know? For me, I don’t have any children, but I have lots of nieces and nephews and kids’ friends who call me Aunt Jeanne, so I buy a lot of toys this holiday season. I don’t buy a lot of toys the rest of the year.

[00:07:58] Matt Bailey: Right.

[00:07:58] Jeanne Jennings: So, that really is a smart way to handle folks like you and I, where there’s a time of the year when we’re interested in these products, there’s other times when we’re not. So, that is actually a really smart thing for companies to do. It brings us to something else though, that I wanted to talk about, which is when you start mailing those inactives, and you’re not mailing them the rest of the year, which is a good practice, suddenly your audience is a little different on your list. So, those inactives who are only mailed during key times less frequently may not behave like the rest of your list does.

[00:08:31] Matt Bailey: Right.

[00:08:32] Jeanne Jennings: So, that’s why it’s important, as I said, in early December to take stock of where you are and see how things are performing. It’s also a good time to do some A/B split testing, because there’s this conventional wisdom that you should never A/B split test during your, your key times. Just don’t do it. And I’ll tell you, I, I strongly disagree with that after years and years in the industry, because holidays are just a different time. You’re going deeper into your file, they aren’t necessarily the same people on your list, the needs are a lot different during holiday for most people than, for e-commerce companies than they would be during the rest of the year.

So, it’s actually really important to test around this time, as long as you do two things. One is you have to test using scientific methods. So, you don’t just test willy-nilly, “Oh, let’s just make the call-to-action buttons purple and see what happens.”

[00:09:17] Matt Bailey: Right.

[00:09:17] Jeanne Jennings: That’s, that’s not a hypothesis. You want to have a, a sound idea for why what you’re testing will boost performance is the first piece. And then the second thing is whatever change you’re making to boost performance needs to be something that you can implement for future email marketing messages during the holiday campaign. So, for instance, last year, again, conventional wisdom out the window, we did a three-way A/B split test with our first Black Friday email.

[00:09:44] Matt Bailey: Wow.

[00:09:44] Jeanne Jennings: Now, a lot of marketers would go, “Oh my God, are you crazy?”

[00:09:47] Matt Bailey: Right. Yeah.

[00:09:48] Jeanne Jennings: But no, we were not crazy because we had our control, we had test A, we had test B. Test B generated a 38% lift in revenue generated per email sent.

[00:09:59] Matt Bailey: Wow.

[00:10:00] Jeanne Jennings: Which is pretty good, but let me tell you about test A. The lift on test A was even higher. The lift on test A was, hang on. I’ve got it right here. 73%.

[00:10:11] Matt Bailey: Wow.

[00:10:11] Jeanne Jennings: So, basically if we had mailed our control throughout Black Friday, there were five Black Friday emails.

[00:10:18] Matt Bailey: Right.

[00:10:18] Jeanne Jennings: This was a design change that was easy to implement across all of those emails. Uh, we would have left a lot of money on the table.

[00:10:25] Matt Bailey: No kidding.

[00:10:25] Jeanne Jennings: So, after that first send where we did the test, we found out that, that test A did better than the control, we made that design change for sends two to five, and you can do the math on that. A 73% increase in revenue per email, over 4 cents, we’re talking some real money here.

[00:10:44] Matt Bailey: That’s beautiful. I am love, that is absolutely gorgeous. I love that type of thinking, and of course those, those are sexy numbers right there. That’s, uh, that is just amazing. But here’s, I, I, I love what you’re doing because you know, if you’re going to test, you want to test with the most amount of users or the most amount of data that you can gather, and that first Black Friday email is going to be the most you’re going to be sending. So, it makes sense scientifically, as you said, we’re going to, we’re going to test the most, the biggest user pool available.

But something else, and, and this is interesting because I got this question yesterday in one of my trainings, and it was, “How do we analyze a campaign after it’s run so that we can make changes for the next campaign?”

And I challenged that in the training that, why are you waiting until after the campaign to make change, to analyze and make changes? And it goes to the heart of exactly what you talked about right there is, you planned the test and based on the test, we’re going to change the rest of the campaign.

And for some reason, I, I, I just encounter this a lot. That marketers feel we have to wait ‘til the campaign’s over to get data, rather than let’s change when we see opportunity, when we know we need to. There seems to be an aversion to midstream analysis and change.

[00:12:20] Jeanne Jennings: Yeah, I mean, some of it depends on how big your lists are. Now, I’m very lucky my clients have very large lists, so we can get statistically significant results with one send. You have a small list, you, you, you may have to test one thing over a couple sends to get results, but, you know, I think there’s a lot of things going on.

One thing I see with email marketers, I, I have yet to meet an email marketer who isn’t, uh, overwhelmed and overworked, especially during holiday. Um, I told you before we got on the call, I’m in a baseball cap ’cause I was up last night working on holiday for a client.

[00:12:52] Matt Bailey: Right.

[00:12:52] Jeanne Jennings: Um, so I slept in instead of, instead of doing my hair this morning. But, um, but that’s I think the first thing that goes on, uh, email marketers are just, in general, overwhelmed. And so, when it gets to holiday, they’re twice as overwhelmed. And so, you know, I see a lot of companies where they don’t ever take a look at results and reports. It’s all about the send.

[00:13:11] Matt Bailey: Yeah.

[00:13:11] Jeanne Jennings: Because they’re so busy. But it’s so important to look at the results. It’s funny because when I start working with clients, that’s one of the things that I really focus on are the numbers. And like you said, getting the numbers quickly, ’cause you can usually get email results within 24 hours. Um, at least, at least directional results to tell you which way to go, and, and just taking the time and having the time to do it. So, I think a lot of it is time and just, I think a lot of people, you know, email marketing, it’s not difficult to make it profitable because it’s so inexpensive on the front end.

[00:13:43] Matt Bailey: Right.

[00:13:44] Jeanne Jennings: But the problem is it’s a double-edged sword. People are like, “Oh, I’m making a profit. I’m not going to put any money into my email. Let’s see if we can try to make this other channel that’s not profitable, profitable.” And if you think about it, that’s the exact wrong way to do things, right?

[00:13:59] Matt Bailey: Absolutely.

[00:14:00] Jeanne Jennings: Because if email’s profitable and you put a little more money into it, it will be a lot more profitable, just like the test that we just talked about. So, you know, sometimes it’s easier to put money, something that’s working well, and get better results than it is to put money on something that’s not working well and try to, try to get it to be profitable.

[00:14:18] Matt Bailey: Uh, that is one of the first lessons I learned as a brand new, very green marketer. And of course, I’m coming from digital and I’m talking with, you know, a 40-year experienced catalog marketer. And we’re talking about things and I’m like, I try to explain, “Hey, that’s not working. We could analyze that and figure out how to make it work.”

And he said, he just looks at me and goes, “Or we could put the money into something that’s already working.” And he, now, very patiently walked me through that. And it just changed my whole view of things that, yeah, so much of what we do has its basis in direct marketing. And that is what a direct marketer, “What’s working? We throw more money there. We put more attention there because that is what is driving it.” And for some reason, I think marketers are just in love with new channels and…

[00:15:16] Jeanne Jennings: It’s bright and it’s shiny and it’s sexy.

[00:15:19] Matt Bailey: Yeah.

[00:15:20] Jeanne Jennings: But you know, if your, fill in the blank, if your social media, if your search engine marketing, if you’re whatever isn’t working, if your SMS isn’t working, don’t, don’t just keep throwing money at it.

[00:15:30] Matt Bailey: Right.

[00:15:30] Jeanne Jennings: Put money at the things that are working and make them better.

[00:15:33] Matt Bailey: Yeah. And, and I, you know, I think there’s a case to be made for, if it’s not working, A, you’re probably not doing it right. B, it could be the wrong channel. Uh, but then why, and I’ve seen retailers do this. I’ve seen so many companies do this. They take money out of the campaigns that are doing well, and put it, not even invest. Invest, it, it, it implies you’ve done some research. It, it’s a hope-based initiative, that we hope putting more money here will make it work.

When, and, and there’s a double-edged sword, like you talk about, not only am I taking money away from a channel that is proven and works, but when you know your, your return on ad spend, for every dollar I put in, I’m making 30 or 40. If I take dollars out of that, I’m not just taking dollars out. I’m taking revenue out, multiplied by the dollars I’m taking out. And so, now it’s not just you’re exploring another channel, you’re moving profit out, and you will not realize that. And it’s kind of basic stuff, but yet I’m running into this constantly, uh, with retailers as they try and make these decisions.

[00:16:52] Jeanne Jennings: Yeah. You know, it’s really hard because, you know, the bright, shiny stuff is very sexy, and people want to be there. Um, you know, throughout my career I’ve been on these panels on stage where I’m on one side alone…

[00:17:03] Matt Bailey: Oh.

[00:17:03] Jeanne Jennings: …and there’s a bunch of people on the other side, and usually they’re younger than I am.

[00:17:07] Matt Bailey: No.

[00:17:08] Jeanne Jennings: And the title of the, the title of the session is “Email is Dead.”

[00:17:11] Matt Bailey: Right.

[00:17:11] Jeanne Jennings: Long live brand new shiny, sexy channel.

[00:17:14] Matt Bailey: Yep.

[00:17:15] Jeanne Jennings: And, you know, none of those shiny, sexy channels have yet to unseat email as the number one channel in terms of ROI, which…

[00:17:24] Matt Bailey: And you’ve been doing those panels for 20 years. Let’s, email’s been dead every year for 20 years.

[00:17:29] Jeanne Jennings: Yeah. Yeah. I mean, RSS was going to kill email.

[00:17:31] Matt Bailey: Right. Where’s that?

[00:17:32] Jeanne Jennings: Right?

[00:17:33] Matt Bailey: Yep. Yep. Exactly.

[00:17:34] Jeanne Jennings: So, uh, so yeah, so I think, you know, there’s so much to be had in email, and like I said, just because your email marketing is profitable, don’t think that you’ve, you’ve done all you can do.

[00:17:44] Matt Bailey: No.

[00:17:44] Jeanne Jennings: Um, put some more money into it, do some, you know, do some scientific method strategic testing. Um, there’s so much you can do if you just sort of dig in, but you know, the other thing about it is, I’m a geek. I actually love email. I mean, I was up late last night working on this for a client and it was fun.

[00:18:02] Matt Bailey: Yeah.

[00:18:02] Jeanne Jennings: Like, I would rather do this than sit in front of the TV. Um, and so that’s the only thing I think that you really want to have. You want to have someone on your marketing team, on your email marketing team who has passion for it. Um, and I think that’s one of the things, well, the first thing that goes when people get overworked and they feel like it’s all about the send, and they feel banged upon.

So, that’s another thing I try to do with my clients is really, I have so much passion and, and, and I hope that it’s, uh, infectious, uh, the idea that I can get in there and show people what they can do with email and how they can do A/B split testing and make it kind of fun. And that’s the other thing I really try to do because it is such a great channel and it can be, I mean, working on holiday email marketing campaigns is just a blast.

[00:18:42] Matt Bailey: Oh, yeah.

[00:18:43] Jeanne Jennings: Um, it is such a privilege. And like I said, I just really jam on it. I’ve been doing it, you know, forever, um, with different, uh, e-commerce, uh, companies, and, uh, it’s just really fun. So, you have to have that passion.

[00:18:55] Matt Bailey: Well, it’s very evident when I talk with you. And, and I think that you hit upon a real key there, that if you’re not having fun, you know, thinking about the campaign, how is this going to happen? How, how can we test it?

You know, coming up with all the variables, if you’re not enjoying it, then it’s time to look for something else, because if you don’t have that passion, that fun attitude of approaching it, then it’s going to be reflected in the quality of the campaign. You’re going to be going through the motions rather than looking at this, like you, I mean, when I’m teaching, when I’m developing curriculum and, I’m like, I am loving it. How can I teach this in a way, in a different way that someone will remember it?

[00:19:38] Jeanne Jennings: Yes.

[00:19:38] Matt Bailey: How can we say this or present it? I love doing that, and I can’t imagine doing anything else.

[00:19:44] Jeanne Jennings: Yeah.

[00:19:45] Matt Bailey: And that’s, I think what it takes to, you know, to really be amazing at what you do.

[00:19:51] Jeanne Jennings: Yeah. I’d, I’d say that’s a big part of my success and I feel lucky that I like something that I’m good at, that people are willing to pay for. But, uh, but yeah, no, that’s, that’s exactly it. And you know, there’s so many little tricks with email. I mean, um, the other thing that I like to play with, not only in holiday, honestly, just all the time are what I call strategic resends.

[00:20:00] So, strategic resend, a lot of people do resends. They just take the same email, and they mail it to everybody again. Nothing wrong with that, but a strategic resend is a little different. So, what makes it strategic? So, the first thing is I’m targeting the people who are most likely to respond, which are the people who got very close to a purchase, but didn’t make one, which means people who clicked, but didn’t buy. So, right off the bat, that’s going to be a small portion of that initial send. I mean, usually click through rates are like 3% give or take.

[00:20:42] Matt Bailey: Right.

[00:20:42] Jeanne Jennings: So, it’s a small portion. So, that’s the first piece is just sending to those people. The reason for that is they have a high propensity to buy ’cause they were definitely interested. The other thing is when we do these, those people rarely are going to unsubscribe or report you as spam because the email is completely relevant to them.

[00:20:59] Matt Bailey: Yes.

[00:20:59] Jeanne Jennings: The second key is to deploy that, that, that resend within a week to 10 days of the initial send, so that the, the memory of being interested in clicking through is fresh in their mind. The third key, which sounds crazy, is not making any changes to that email.

[00:21:15] Matt Bailey: Ha.

[00:21:16] Jeanne Jennings: Because whatever was in that email the first time got them to click, they were this close to a purchase, so when you send it again, typically not only do they click again, but a big percentage of those folks buy.

[00:21:27] Matt Bailey: Wow.

[00:21:27] Jeanne Jennings: So, for instance, last holiday, we did resends for almost every send that we did. We had an average lift from the initial send in RPE of 1380%. The median lift was 953%.

[00:21:43] Matt Bailey: With the same email.

[00:21:45] Jeanne Jennings: The same email. Now, again, the key is that it’s a, it’s a small audience, so it’s not like, it’s not like 10 times the revenue of the initial send…

[00:21:52] Matt Bailey: Right. Right.

[00:21:52] Jeanne Jennings: …but if you don’t do that strategic resend to those, that small group of people…

[00:21:57] Matt Bailey: Yeah.

[00:21:57] Jeanne Jennings: …who was so close to the purchase, you’re just leaving that money on the table.

[00:22:01] Matt Bailey: Wow. ‘Cause like your conventional wisdom would say, you know, I’m sending the same email. They would think to themselves, “I’ve seen this before.” Uh, but yeah, numbers don’t lie. I mean, that’s, that’s interesting. Yeah, because I would, I would be one of those that were like, “We can’t send the same thing, that’s…” But that may, wow. That is amazing. Amazing.

[00:22:24] Jeanne Jennings: Yeah.

[00:22:24] Matt Bailey: But yeah, a highly qualified group of people that they qualified themselves. Um, but yeah, that, that blows my mind. The same exact email would push them over the edge on a second send.

[00:22:36] Jeanne Jennings: The nice part about that is the resources it takes to do strategic resends are almost nothing.

[00:22:41] Matt Bailey: Right.

[00:22:41] Jeanne Jennings: I mean, it’s very easy to pull the list of people who clicked on the last email, um, it’s very easy to dedupe it against people who bought, and it’s very easy to tee up that exact same email again and send it to that list of people who clicked on the first one.

[00:22:56] Matt Bailey: Wow.

[00:22:57] Jeanne Jennings: So, that’s the other nice thing about strategic resends, the investment is very small, but the return is significant.

[00:23:03] Matt Bailey: Yeah. Great. That is amazing. One other thing, I mean, as we were comparing email to different channels, one of the things that I absolutely love about email is there is a clearer attribution path to email because it is so much more of a closed system than many of your other channels, which rely on third parties or other platforms, third-party platforms, that type of thing.

And so, one of the things that I’ve heard over the past year or two is more drive to attribute. And in some ways, it’s near impossible, but yet when we want to look at probably your best method of measuring attribution in terms of marketing, email is right there.

[00:23:47] Jeanne Jennings: Oh yeah.

[00:23:47] Matt Bailey: It’s almost like a direct one to one.

[00:23:49] Jeanne Jennings: Yeah. Um, you know, so most email uses last click attribution, um, which is the easiest to measure. Um, I’ve had people argue and debate me about how it’s not an absolute measure of attribution, which I don’t disagree with. I mean, anytime we click on an email, there’s a good chance that we’ve had another email about that, or we saw a display ad, there’s so many things that go into a person’s decision to purchase.

[00:24:15] Matt Bailey: Right. Right.

[00:24:16] Jeanne Jennings: Now that said, a lot of those things are very hard to track, especially, you know, if you’re, if you’re a smaller customer or you don’t have a whole ton of time. So, last click is a pretty good relative sense of, of what’s driving it. So, yeah, taking a look at that.

The other thing about attribution is, if you don’t understand the attribution modeling that your company’s using, you should look into it and understand it. I did, um, a project for Verizon a bunch of years ago, all around attribution. When you’re doing an attribution model it’s, typically it’s last click, but then there’s questions around that. So, how long after that last click until the purchase do I get credit for?

[00:24:57] Matt Bailey: Right.

[00:24:58] Jeanne Jennings: If, if the click happened a day before the sale, do I get credit? Probably. If it happened a week before the sale, and that was my last click before the sale, do I get credit? Most likely. If that last click was two months before the sale, do I get credit? Some models do, some don’t. Um, the other thing to ask is, do you get credit just for the product that was, that was promoted in that email or do you get credit for the whole cart? Which is another interesting question.

[00:25:22] Matt Bailey: That is. Yeah.

[00:25:23] Jeanne Jennings: So, there’s all sorts of different, there’s all sorts of different models. So, if you don’t know how your company is tracking attribution, you should, um, you should ask because it’s important thing to understand, and it could really change how you do your email marketing. If you know that your attribution window is only a week, you’re probably going to want to be touching people at least once every seven days…

[00:25:41] Matt Bailey: Right.

[00:25:41] Jeanne Jennings: …to make sure you get credit for these sales. If your attribution model is, is a month, then probably you don’t have to be as aggressive about it.

[00:25:49] Matt Bailey: Yeah. And I think part of this, too, and, and it’s a great discussion when, when you start looking at different attribution and things there, and one of the things I’ve really been pushing back on is especially the display in the attribution path, because just look at the click rates of email versus display. Email has much higher click-through rates than display ads. And to me, this gets to the, I’m going to invoke Marshall McLuhan. The medium is the message. People trust email more than they trust the display ad. And so, if I’m looking at attribution, I would be seeing that because display gets such a low click through rate, I don’t think that’s an effective means.

But also, here, the other part of it, of what came out in a lot of this Facebook dump is they will tell you that you had a view, however, Facebook’s definition of a, a, a display view is zero pix-, greater than zero pixels and greater than zero seconds. How am I supposed to give that attribution with that definition?

Uh, whereas email, I’ve got a click. I know they saw it. There’s, there, there’s strengths and weaknesses when we start talking about attribution, it’s just not a clear cut, “We know that that was involved in the process.”

[00:27:15] Jeanne Jennings: Yeah. I’ve worked with companies where, you know, email needed to get a click, but if there was a display ad impression that got credit, partial credit or full credit, even if it happened previous to the final click. So, there’s, like I said, there’s all different ways that companies do it. It’s just important to understand how your company does it so you can understand what’s going on. It’s, it’s almost like, it’s almost like understanding the rules of the game so you can play it right.

[00:27:40] Matt Bailey: Right. Not only the rules, but the definitions.

[00:27:43] Jeanne Jennings: Yeah. Yeah.

[00:27:44] Matt Bailey: I find a lot of companies internally don’t agree on definitions. Then and you, you put in an agency which has their own set of definitions. And then, you know, like I’m trying to tell everybody now what Facebook’s definition of a view is, so that you understand, when you talk about a view, how little it means, and, and that’s if we, and that’s if a human viewed it. We’re not even, you, you know, talking about, you know, bots and all that.

So, meet, we need to know what the platform definition is, so that we can adjust what we think, because if I’m presenting to a C-suite and I talk about a view or an impression, they are interpreting that based on their own experience. They, when they think display ad, they think that big old banner in the top of the page that everybody sees, and it takes some level of education that, no, that’s not always what it is.

[00:28:38] Jeanne Jennings: Yeah. You know, that’s always been, that’s always been an issue just in the marketing world. I mean, I remember early on, we had opt-in and we had double opt-in and, and I’ll never forget speaking to someone at a conference, God bless them, and they said, “Well, we practice double opt-out.” And I said, “Well, I’ve never heard of that. What does that mean?” This was before CAN-SPAM, and they said, “Well, that means if you click to unsubscribe from our list, we’re going to send you an email and you need to click on that email to confirm that you really want to get off the list. Otherwise, we won’t take you off.”

Which is, of course, why we have CAN-SPAM, but it’s just so funny to me ’cause, you know, you hear double opt-out and you’re like, “You mean double opt-in,” and he’s like, “No, no. We mean, I mean, double opt-out. You have to tell us twice to take you off the list or we won’t do it.” Which of course you could never do now with CAN-SPAM, thank goodness. But terminology is very tricky, and people bend it to their own means.

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[00:31:09] Matt Bailey: Yes, I, well, and I’m about to report a company because I got a, I don’t even know how I got on this list. I hit unsubscribe. It showed me two options and it was basically I had to check them, but it was worded in a way that was just kind of odd. And, and then I started looking at the page more in-depth and I noticed there were other dropdowns that were condensed.

And when I opened them, I’m on 20 different, you know, lists and, oh, I was furious by the time I looked at that and it was all, it was all presented and written negatively in order to confuse. And it was probably the worst opt-out experiences I’ve ever seen. Um, but, oh my goodness. And, and that’s why, I’m not laughing, I’m crying because it’s still, that mentality is still there.

[00:32:05] Jeanne Jennings: Well, and you know, the good news is, I mean, I, I tend to work with name brand companies. I tend to work with bigger companies and, and, and they don’t, they don’t do things like that because they know that their reputation’s at stake.

[00:32:14] Matt Bailey: Right.

[00:32:14] Jeanne Jennings: I mean, you know, the New York Times, if you want to get off their email list, they want you to get off their email list. They’re not going to try to trick you into staying on. But yeah, I think a lot of other brands out there don’t understand, you know, how damaging this is to your brand reputation. And honestly, it’s not even about CAN-SPAM or getting a fine from the government, it’s about what it’s doing to the relationship of trust with the people on your email list, who you’re trying to have a relationship with because relationships are what drives purchases, and this kind of stuff doesn’t lead to a good relationship.

And not only are you going to have a bad experience, you’re going to tell your friends, like me and everyone who’s listening to the podcast about that bad experience. Now, we’re not going to mention brands here, I’m sure, but it’s, it’s, it’s damaging, and I think that’s another problem with email. People don’t understand that the reason you, you, you follow the standards of best practices is it’s in your own best interest to protect your brand.

[00:33:10] Matt Bailey: Right.

[00:33:10] Jeanne Jennings: And when people try to get around it, it reflects poorly on you, it’s actually a bad idea.

[00:33:16] Matt Bailey: Well, and it’s, I think we, we’ve used this, this metaphor since day one. Would you do that in real life?

[00:33:23] Jeanne Jennings: Yeah.

[00:33:23] Matt Bailey: Would you prevent someone from walking out of your store in real life by making them, you know, “Yes, I want to leave. I really, really…”

[00:33:31] Jeanne Jennings: “I’m sorry, I’m barricading the door. Are you sure that you want to go? I just need to make sure that you actually intended to leave.”

[00:33:40] Matt Bailey: Absolutely. Yeah, we would never think of doing that in real life.

[00:33:44] Jeanne Jennings: Never do that.

[00:33:44] Matt Bailey: But digitally it’s so easy and it’s a shortcut and yeah, for some reason, things like that have just taken hold of people’s imaginations. Uh, and, and they just develop these, these mazes to get out of.

[00:33:58] Jeanne Jennings: Yeah. You know, it’s, it’s desperation and if you’re…

[00:34:01] Matt Bailey: Wow.

[00:34:01] Jeanne Jennings: des-, if you’re that, if you’re that desperate, then, then you need, you need to change something about your program because companies that are doing email marketing well are not that desperate.

[00:34:11] Matt Bailey: Wow. That is powerful. That is a powerful observation. That, wow. Wow. Okay. So, we have gotten way off track on holidays. So…

[00:34:22] Jeanne Jennings: Let’s go back to talking about Christmas in November.

[00:34:25] Matt Bailey: Yeah, let’s do that, that is holidays. So, I see a lot of articles about when to send emails. Is there credence to, you’ve got to send on the Friday after Thanksgiving. You have to send this, or, you know, some of these where you have to send on this day, at this time, how much stock should we put into that type of research or, or advice?

[00:34:50] Jeanne Jennings: So, all those articles about the best day and time to send email…

[00:34:53] Matt Bailey: Yeah.

[00:34:53] Jeanne Jennings: And they used to be published a lot. It’d be like, “Thursdays at three o’clock is the best time to send email.”

[00:34:58] Matt Bailey: Yes.

[00:34:58] Jeanne Jennings: So, of course I, you know, we would all, all of us who were speaking at that time would get questions about that, and I would say, “You know what, here’s the thing. If everyone who reads that article follows that advice, the best time to send email is anytime but Thursdays at three. ‘Cause people’s inboxes are going to be bombarded.”

[00:35:13] Matt Bailey: Right.

[00:35:13] Jeanne Jennings: So, you know, as far as best day and times to send in general, it, it really, you want to look at your audience and figure that out, and you can do testing. You know, we did, uh, last year for holiday we actually, we started with two sends a week, and then we were going to add in a third send. So, our 2 sends a week, I think it was Tuesdays and Thursdays. And then we’re going to add in a third send, and we actually did testing to see whether Monday, Wednesday, or Friday was a better day.

I think that’s what it was. But we actually sent the same email different days at the same time, and one was the clear winner. So, that was our third day. So, you can actually test into which days are best. You can also test into which times are best in general. You know, as far as holiday and things like Black Friday, Black Friday is so much bigger than any one retailer. I mean, it’s a thing, man.

[00:36:03] Matt Bailey: Oh, yeah.

[00:36:03] Jeanne Jennings: And so, you really want to make sure that you don’t miss out on that, because there’s a, there’s kind of a shared psychology about it. Good deals. Everyone’s shopping. I haven’t been a Black Friday shopper for years, but you know, back in the day, I remember getting up early and going to Macy’s for that coat that I wanted, that was going to be on super deep discount before 8:00 AM, you know? But you want to be there because everyone else is there, and that’s what they’re focused on.

You know, it was interesting last year, because in addition to Black Friday, we had an Amazon Prime day during the holiday season. I believe that was in October, if I’m not mistaken, and it’s interesting because they announced it just a week or two before, but we knew that it was going to happen, so we actually developed a campaign for it, because our feeling was Amazon is, is arguably one of the biggest retailers out there, if not the biggest. And so, if people are being made aware from them that it’s time to shop, it’s time for the deals, it’s Amazon Prime day, we wanted to provide a similar, uh, experience in our emails to be like, “Hey, it’s not just about Amazon. We can, we’re going to give you deals, too, right now.”

So, you want to make sure that you jump on the boat at those times when kind of the world is thinking about shopping and the world is looking for discounts. Um, I think with Black Friday, as I mentioned with my client last year, we did five emails. One of the biggest mistakes I see clients making around things like those limited time sales is they don’t send enough emails.

Which sounds really crazy, but I’ve talked to people, you know, who are like, “Well, we send one when it starts, and we send one to tell them it’s about to end. And that’s it.” And the problem with that is, that’s two emails, uh, average open rates on emails pre-Apple Mail Privacy Protection, which is a whole other tangent, but pre-MPP…

[00:37:46] Matt Bailey: Yes.

[00:37:48] Jeanne Jennings: …open rates were running on average 25% or 30%. So, think this through for a minute. If I send two emails and my average open rate for both is 25% or 30%, let’s say it’s 30%. Even if completely different people open both of those emails, that’s only 60% of my audience that’s seen my message. And we know from experience that there’s a lot more overlap than that. You have people who love your brand, who are going to open every email, sending just two emails for a four or five or six day sale, which Black Friday, typically now it’s Black Friday plus Cyber Monday and sometimes it’s extended. It’s just not enough. So, with a limited time sale like that, I tend to send every day.

The other thing you want to think about is urgency is a great way to drive sales. So, you send the first email that the sale has started. You send a reminder that it’s happening. You send a note that says it’s about to end, then you send a note to say, “Hey, it was so popular we’ve extended it another day.” Then you send an email that says, “Hey, actually, this is really actually the end.”

So, the idea is the more, by, by sending those emails and making them work together, again, that’s five emails. If your average open rate is 30%, you have a much greater chance of hitting a higher percentage of your audience. And I’ve done studies on this, we call it “reach” and there’s “open reach” and there’s “click reach,” which is over the, of course, of a bunch of emails, what percentage of your audience opens or clicks on at least one?

And so, that’s what you want to do. And there’s a point where more emails aren’t going to increase your open or click reach. That’s too many, it’s kind of a bell curve, but that’s why I think a lot of people, especially for limited time campaigns, they don’t send enough emails, and again, they’re leaving money on the table, which I hate to do.

[00:39:24] Matt Bailey: Right, right. Wow. I, I feel like I’m getting the inner secrets here because this is, some things, you know, you know, we, and, and there is a lot, I hate to say, there is a lot of marketing that is gut instinct, rather than, everyone says they want to be data-driven, but to get the data, and like you’re saying, we’re sending every day, look at the data. And the, but what prevents that data from actually being gathered in the first place is, “We can’t send every day. It’ll, we’ll, they’ll get tired of us. They’ll unsubscribe.” It’s that fear of actually doing it to get the data and see if it’ll work in the first time.

[00:40:00] So, I love that you’re just, you bring, you’re not only bringing the, the practical, “Here’s what to do,” but “Here’s what it does,” and I love it. You can’t argue with the data. It’s great. It’s great.

[00:40:12] Jeanne Jennings: Yeah. I had a client years ago for Black Friday. So, they were one of those, um, shopping sites that watched all of the fashion brands and would let you know when things were on sale. For Black Friday, they sent seven or eight emails over the course of that single day.

[00:40:26] Matt Bailey: Oh yeah.

[00:40:27] Jeanne Jennings: Because it was like special alerts. “Hey, we just saw that Everlane has a sale on this, and it’s the best price we’ve seen all year.” “Hey, here’s another email. We just saw that Madewell is selling this, and this is the lowest price we’ve seen all year.”

[00:40:39] Matt Bailey: Wow.

[00:40:39] Jeanne Jennings: And, and you know, some people go, “Oh my God, seven emails in one day, that is too many.” It totally made sense for the content they were sending. If they had waited and put them all in an email at the end of the day, it wouldn’t have been as effective, things would have been sold out. So, you want to think about the content you’re sending and how you can make it useful to the subscriber. They did not see an uptick in unsubscribes, they did not see spam complaints, because the content was relevant, and they knew their audience. Their audience wanted that.

[00:41:05] Matt Bailey: Well, and their audience is probably sitting there on Black Friday, doing all their shopping online. And so, getting those along with all your, your shopping confirmations and receipts and all that, oh my goodness. That, that is such a perfect application. That, that, that’s wonderful.

[00:41:19] Jeanne Jennings: Yeah, I mean, it’s almost like a customer service, right?

[00:41:21] Matt Bailey: Yeah.

[00:41:21] Jeanne Jennings: “Oh, here’s, here, here it is on sale,” and it’s, you know, you’re looking at these, you’re like, “Oh wow. That would be a great gift for Pam. Oh, let me go get that. Oh, that would be a great gift for Mark. Let me go get that.”

[00:41:29] Matt Bailey: Right.

[00:41:30] Jeanne Jennings: So, it’s almost like it’s a customer service ’cause they’re giving you ideas and they’re giving you discounts at the same time.

[00:41:34] Matt Bailey: Wow. Very, very cool. Alright. So, you brought this up and it’s probably time to bring this up and that’s Apple’s Privacy Protection. Okay, that tells me, okay. We can move on. That, that sigh told me everything I need to know.

[00:41:49] Jeanne Jennings: No, no, no, no, it’s, it’s a really important topic, and it’s, it’s the thing that’s been keeping, uh, email marketers awake at night since it was announced back in June, and, uh, I think it’s really interesting because my, my thinking on it has really evolved since the beginning.

[00:42:04] Matt Bailey: That’s good because I think that’s typical of any major change. There’s the initial, “I hate it.” And then we, months later, I think there’s a softening and even maybe a, “Okay.” You know, more than just an acceptance, maybe an appreciation, but sounds like you’ve gone through those stages of grief.

[00:42:23] Jeanne Jennings: I’ve gone through the stages of grief. So, you know, initially we were all very concerned. For those of you who aren’t familiar, Apple’s Mail Privacy Protection was launched with iOS 15, which was available to download in September. Um, basically what it does is it’s a pop-up and it basically says, um, “We want to help protect your privacy. Click on this, and we will make sure that marketers can no longer see, you know, whether you open their emails or not, where you are when, when you open their emails.”

There’s another initiatives called like, “hide my email,” but the biggest one was the impact to open rates. So, basically by clicking on that, and the way it’s worded, it really sounds like they’re protecting you from something dangerous. Then what they do is, they will basically, the way that we track opens is through an invisible pixel image in the email.

So, if you enable Apple’s Mail Privacy Protection, what they’re doing is they are downloading all the images in the email before you ever open it or see it, and that way it looks like you opened it, even if you didn’t. So, the initially our, our thing was, “Wow, open rates are going to explode,” and it’s not just Apple email addresses. It’s anyone who’s opening email on an Apple device. So, if you’re using the native phone app on your iPhone, even if you have a Gmail account that you’re pulling into that native app on the iPhone or any other account, it would impact it.

[00:43:44] Matt Bailey: Wow. Yeah.

[00:43:45] Jeanne Jennings: Um, so, initially we were all anticipating that open rates were going to blow up, we weren’t going to be able to tell which of these people really opened and which where the images were just cached and, and that that was going to make open rates unusable. And that was kind of “the sky is falling view.” There was a lot of talk about ESPs, parsing out, Apple opens from other opens so you could still get a clean read on your other opens.

But again, that gets much more difficult because it’s not just an Apple email address. It’s any email address that’s open on an Apple device, and they could cache it on the Apple device, then if you opened it on non-Apple device, it would still trigger an open there. So, the whole thing gets very confusing.

What ended up happening, typically when Apple rolls something like out, like this out, it is rolled out to the entire population in a six or eight week period. So, they don’t sort of say, “Okay, now everybody download it today,” ’cause that would crash their servers.

[00:44:36] Matt Bailey: Right.

[00:44:36] Jeanne Jennings: They’re like, “Okay, this, you guys get it today. A different group gets it tomorrow.” They, they stagger the rollout. What we’ve seen here is that staggering is much, much slower than it’s been in previous, uh, version updates. Uh, we don’t really know why that is. We think it might be because if you can imagine caching all these images, this is pretty new, and it’s a lot of, a lot of, uh, a lot of storage space.

[00:44:57] Matt Bailey: Right.

[00:44:58] Jeanne Jennings: So, it’s been a slower rollout than we anticipated. As a result, some of us are seeing slight upticks in open rates, but we haven’t seen anything dramatic yet. It’s interesting because the open rate, when we could start tracking opens, which was back around the 2000 timeframe, I remember it. There was a lot of controversy about open rates.

[00:45:15] Matt Bailey: Right.

[00:45:15] Jeanne Jennings: There were actually nights at conferences, late at the bar when it was closing, when people would almost get into fisticuffs over open rates, you know, “They’re, they’re a B shit metric. Don’t use them.” “No, they’re valuable.” You know, uh, I can remember one night we were separating people in the lobby ’cause we really thought they were gonna, they were gonna start duking it out. Um, so it’s funny because we went from that in 2000 to now then being pretty much accepted. Although anyone who really works, understands there’s always this margin of error in open rates.

[00:45:47] Matt Bailey: Yes.

[00:45:47] Jeanne Jennings: The reason is, and the reason people were against them at the beginning is that it involves that pixel. So, you could read an entire email with images disabled…

[00:45:55] Matt Bailey: Yep.

[00:45:55] Jeanne Jennings: …10 times, and it wouldn’t count as an open.

[00:45:57] Matt Bailey: Right. Yep.

[00:45:58] Jeanne Jennings: You could breeze by it in your brows-, in your, in your preview pane with images enabled, and it would count as an open, even though you didn’t look at it. So, that margin of error’s always been there. So, my thinking on how we’re going to handle this, especially since the rollout has been so gradual, I think we’re just going to assume that there is just now a higher margin of error in those open rates, and just move forward and keep using them, because the way that we got around that margin of error, you know, back in the, back in the 2000s, when it was first launched was by saying, “You know, if you are mailing to your list again and again and again, the margin of error should be about the same for every send.”

[00:46:38] Matt Bailey: Right.

[00:46:39] Jeanne Jennings: ‘Cause you’re mailing to the same people.

[00:46:40] Matt Bailey: Yes.

[00:46:40] Jeanne Jennings: So, if you use that logic with Apple MPP, even though the number is going to be higher, it’s not an absolute figure for opens, it’s still a relative figure, the margin of error is higher, but again, if you’re sending to the same list, your house list over and over and over, which is what you should be doing, that margin of error should be about the same for all of your sends. So, open rates, as they always have been, are still a, a decent directional metric, not absolute, but directional…

[00:47:08] Matt Bailey: Yes.

[00:47:08] Jeanne Jennings: …to see what’s going on. So, I, I think that we all thought the sky was falling and that we’re actually gonna move forward and just use them like we always have, understanding that larger margin of error. I could be proven wrong. This is a pretty, kind of a controversial stance right now, contrarian view, but I, I honestly, I can see a world where that’s just how we handle this.

[00:47:29] Matt Bailey: I love the contrarian view. That is, uh, I have been accused of being contrarion, which I thoroughly disagree with, but that is…

[00:47:37] Jeanne Jennings: So yeah, so that was probably a longer answer than you wanted about Apple MPP, but…

[00:47:41] Matt Bailey: No, no, that, uh, you know, and, and in my training, I mean, I tell people, you know, open rate is muddy. It, it, it’s a, it’s a muddy metric.

[00:47:51] Jeanne Jennings: Yeah. Always has been.

[00:47:52] Matt Bailey: Yeah, because I, my mantra is, “If it’s clickable, it’s trackable.”

[00:47:57] Jeanne Jennings: Yes. Yes.

[00:47:57] Matt Bailey: That’s, that’s what I focus on, is if it’s clicked, it’s tracked. Open is muddy because, you, you know, I, I think of my, my email client, I’m using Outlook, which naturally if you are not added as a trusted sender, naturally all the images are blocked, but, and I’ve realized that there are times where I’ve got someone sending me something, I’m like, “Oh, I’m,” you know, “I haven’t added them to my trusted sender yet.” And it’s probably been, you know, a year or two or something like that.

And it’s, so you’re relying on, and, and I think so many times, sometimes maybe we attribute more conscious decision-making on the part of our recipients than there actually is. People are people. When I’m looking at email, it is a functional, I’m there to accomplish something and get out. Uh, I’m trying to clean that inbox. I’m not looking at, you, you know, providing feedback to retailers.

[00:48:54] Jeanne Jennings: Exactly. I think, you know, that’s the other thing marketers get mixed up about. We care more about these emails than the people who getting them to.

[00:49:00] Matt Bailey: Yes.

[00:49:01] Jeanne Jennings: Um, you know, I’ve had marketers like, “Oh my gosh, there was a typo in the second sentence in the fourth para, paragraph. Should I send a, should I send a, you know, uh, uh, an oops email? Should I let them…” and I’m like, “No, just let it go, because probably very few people noticed that.” Now, if you had a link that didn’t work, that is a reason…

[00:49:19] Matt Bailey: That’s…

[00:49:20] Jeanne Jennings: …to send an oops email, but yeah, we care a lot more about all this than any of the recipients do. Um, and, and that’s a good thing on the one hand.

[00:49:29] Matt Bailey: Yeah.

[00:49:29] Jeanne Jennings: It’s why we, why we’re good at our jobs, but we have to remember that sometimes when we’re thinking about, you know, “Why didn’t they open it? Don’t they love us anymore?” They’re, they’re not thinking about that.

[00:49:40] Matt Bailey: Oh, okay, so I have a non, non-holiday topic that I want to throw at you. And this is a curve ball. I completely, so, here’s the line of thought. You brought up misspelling. I was looking at someone’s campaign and saw, like, they had one campaign that was like really far and above the open rates, response, things like that.

[00:50:00] And it was because they had a horribly misspelled word in the, in the, uh, in the subject. And, you know, and their question was, “Should we do this more often?” And, and I said, “Okay, now you’re thinking like machine learning, because machine learning would say…”

[00:50:22] Jeanne Jennings: Right.

[00:50:22] Matt Bailey: “…if we put a misspelling here, it increases the, the goal, which is opens and clicks, and so, let’s do this again.” Which leads me to the question. AI writing, uh, subject lines, writing emails, what are, I keep making these sighs come out of you.

[00:50:43] Jeanne Jennings: I’m sorry, Matt. I’m sorry.

[00:50:44] Matt Bailey: Dear listener, this is not on video. We, we’re on video so that we can watch each other during this.

[00:50:49] Jeanne Jennings: Yeah.

[00:50:49] Matt Bailey: And if you could see the reactions of her, her, her face, the, the, the demeanor, the shoulders went down, the sigh came out. I, I feel like I’m beating Jeanne up here because…

[00:51:01] Jeanne Jennings: I’m really sorry. I, I like I said, I’m a little overtired, so I’m not necessarily at my best.

[00:51:06] Matt Bailey: Well, I told you this was coming out of left field, but…

[00:51:08] Jeanne Jennings: That’s ok. I can handle this one.

[00:51:09] Matt Bailey: …the misspelling got me on to what are you seeing with AI, I know there are people that are like cheerleading this, “Ah, AI is going to transform everything. It’s going to do all our work for us,” which I, contrarian, I, I’m very, very skeptical, uh, about that, and I would love to hear your opinion on that.

[00:51:31] Jeanne Jennings: Yeah. Years ago, I had breakfast with one of the bigwigs from one of the big ESPs, and I was pitching them that they should introduce me to their clients to help them with their email marketing, ’cause I could help with strategy, and if their clients had better results, that would make them happier, and there was a whole pitch here. And I’ll never forget, ’cause he says to me, “Oh no, we don’t need anyone to do strategy. The system handles that.” I’m like, “What?”

[00:51:56] Matt Bailey: Wow.

[00:51:56] Jeanne Jennings: “Yeah, it’s all automated. The system handles all the strategy. We, we would never bring you in to help the clients with strategy, ’cause the system does that.” And, and the problem is, now this was many years ago, but as you and I know, the problem with that is that, you know, with AI, there’s gotta be a person who programs it, machine learning is a little different ’cause the idea is there’s an initial program, and the machine goes off and learns on its own.

But in both of those instances, I think what people don’t realize is you’ve got to have some person setting up the AI and providing information and, and in order for it to work. And, you know, I’ve had some really mixed results with AI. I, I’ve, I’ve tested, I worked with, and, and you know, years ago there were a couple companies that popped up and they were the future of all this, and I’m not sure how many of them are still around, but nobody really touts them anymore. But you know…

[00:52:43] Matt Bailey: Right.

[00:52:43] Jeanne Jennings: …a couple of years ago for a client, we tested one of those AI companies and the subject lines did not perform better than the things we were coming up with ourselves. And what I think there is, that’s kind of an easy fix, it’s like a quick fix for something, but I have not seen a lot of success with AI. I think that, you know, as we get more sophisticated with it down the road, we may be able to leverage it, and there are some companies that are doing some pretty slick things, but they’re, they’re few and far between.

And I think, you know, most people who think AI think that that’s going to solve all their problems, and it really doesn’t. You need to have the knowledge, you know, to inform the AI, and, and even then, I just don’t think it’s there yet. And I think the other thing is, people don’t necessarily use AI in, in the right ways. So, yeah, there are propensity models that I’ve worked with, but even those, you need to tweak them, and you need to look at the results, you need to give them input, I need to help determine what the algorithm for the propensity is.

So, I think what people don’t understand is even when you’re using AI, there has to be a large human component, and I’m not talking like a junior level person, someone who actually understands the business and what’s going on.

[00:53:50] Matt Bailey: Right.

[00:53:51] Jeanne Jennings: So, yeah, I don’t think we’re there yet. I, I don’t, I don’t see a day, hopefully, hopefully there won’t be a day where I’m not needed anymore, and computers can just do what I do for clients with regard to strategy and creative direction and maybe split testing. Um, I, I don’t think I will, I don’t think I will live to see that day. I hope I don’t, but, um, yeah, I don’t, I don’t think it’s there, and I think people are starting to realize that.

[00:54:11] Matt Bailey: I’m with you. I’m with you there, because I think a lot of human behavior can be predicted. However, we’re not just behavioral beings. We’re emotional beings, we’re, there are, there are words that have deeper meaning that I’m not sure a machine could really understand.

And like you said, it, it starts with datasets. It starts with instructions. It starts with, and then I, I, one of the fascinating reads about AI is do you have, also, a multicultural component? Because if you’re using a, a data set that does not include additional cultural elements, additional, you know, input from other viewpoints, you could seriously damage your brand by creating something that is exclusive of other people, other groups, uh, and, and could be downright offensive.

Uh, so, that I think is what has caused people to back off of a lot of the, “Ra-ra,” uh, “AI is gonna solve all our problems,” because I think every, about once or twice a year, an article comes out about AI that eventually becomes racist or eventually starts creating content that, that’s not acceptable because it’s learning, and unfortunately, if it’s learning from the internet, it’s not, it’s, it’s like a bad parent.

[00:55:38] Jeanne Jennings: Yeah. Yeah, that’s not the input that we want. No, I mean, you know, and it goes back to exactly what you said about the misspelling. Years ago, I was working with a big brand. We sent a newsletter where the link for the first article didn’t work. We sent a, an oops email, which basically said something in the subject line, like, “Oops, here’s the right link.”

And it got a huge open rate, and I got a great click through rate, and no, no lie, you know, the person in charge of that said, “Hey, I’m thinking we should do this every week.” And I’m like, “Break a link?” And she’s like, “No, let’s just use like, oops in the subject line, like every week.” And I had to explain that, like, it’s gonna wear off. If you do it every week, people are going to start to ignore it. And it’s not really good marketing, you know, it’s like a gimmick.

[00:56:23] Matt Bailey: That would fall under a deceptive subject line, wouldn’t it?

[00:56:25] Jeanne Jennings: Um, potentially.

[00:56:26] Matt Bailey: Potentially.

[00:56:27] Jeanne Jennings: Yeah, but I mean, you know, the thing about, about CAN-SPAM is they, they, they really only, the government really goes after the, the, the most egregious offenders.

[00:56:36] Matt Bailey: Yeah.

[00:56:36] Jeanne Jennings: They don’t really have the bandwidth to go after just everyone. So, I, I, I’m not sure, you know, but it’s just, again, it’s people looking for these short-cuts, and that, that’s not going to work long-term. It’s much better to have a sound strategy to really think through and try to do it smart than try to do it short-cuts and quick and easy.

[00:56:53] Matt Bailey: Yeah. Yeah. That’s like a movie using the, uh, cheap jump scare rather than actually telling a good story. Uh, so yeah, it’s a great, great example, and unfortunately it’s the executive level that’s, “Let’s do that again. That was, that was magic. That was lightening in a can. Let’s do it again.”

[00:57:13] Jeanne Jennings: Um, exactly. You know, and that’s the problem with AI, right? “Oh, that worked really well. That subject line was great. Let’s use it again.” Well, that was a Black Friday subject line. We cannot use that again until next Black Friday.

[00:57:23] Matt Bailey: Wow.

[00:57:23] Jeanne Jennings: It just, it just won’t work.

[00:57:24] Matt Bailey: Wow.

[00:57:25] Jeanne Jennings: So, yeah, there’s a lot of elements of that. So, you know, we may get there, but I don’t think, I don’t think in the next 10 or 20 years AI is going to be taking my job nor yours.

[00:57:35] Matt Bailey: I’m, I’m of the same, same mentality. Best thing I heard about AI is describing it, is AI is like having a million interns, because they do, it does menial work quickly.

[00:57:47] Jeanne Jennings: Yes. Yes.

[00:57:48] Matt Bailey: Um, which I am of the mind that a million interns, it’s not going to do anything quickly, but I understand where it’s going and what it’s doing. Okay. Quick questions.

[00:57:57] Jeanne Jennings: Yeah.

[00:57:57] Matt Bailey: Is there life after Christmas for an email marketer?

[00:58:00] Jeanne Jennings: Oh, yeah. Oh yeah. Uh, you can breathe again after Christmas. I, uh, I, I just, I just remember my years of working with Hasbro, you know, by, by the time Christmas came, my brain would be pretty much scrambled. I would need the next week to kind of get myself back.

Yeah, no, totally. I mean, and, and, you know, the good thing is that, like I said, Christmas is really fun. It’s fun to be an email marketer during Christmas, but by the end of Christmas, you’re really happy to get back to some more, you know, low-key, normal kinds of stuff.

But, you know, you can still take things that you learned in Christmas and leverage them for your regular campaigns. And, you know, one of the things that I like to do with my clients is as soon as Christmas is over, we actually put together a deck, a PowerPoint deck that reviews what we did for the holiday. So, literally every email that we sent gets at least one slide, if not two, we have the results of that send, everything from opens and clicks to conversions and revenue per email generated. We have every A/B split test that we did with all the results, we have all of the strategic resends.

And the idea is when you put it together right after the holiday, while it’s all still fresh in your mind, you can also put notes at the end about next year. “Hey, look at doing this. Hey, don’t do that again.” And it’s also great because then when it gets down to June of the next year, you don’t have to go pull all the data from the last holiday and figure out what to do. All you need to do is dust off this deck, and you’re, you know, you’re, you’re way ahead of the game.

So, um, that’s another thing it’s important to do after holiday, and, and don’t get me wrong. I understand the last thing you want to do when holiday ends is go back and look at all of those holiday emails. I usually try to build that deck as we go, and then at the end of holiday, I just go back and update all the numbers. ‘Cause you aren’t going to have some long tail purchasers, some things that are gonna change.

Um, but that, that is probably what you want to spend the time between Christmas and New Years doing. And that’s, you know, low-key and, and, and even though the last thing you want to do is look at another holiday email, it’s better to just be done with it and set yourself up, set yourself, or your company up for the next holiday season.

[01:00:00] Matt Bailey: When is the last holiday email sent?

[01:00:03] Jeanne Jennings: So, the last holiday email is typically dependent on, uh, what the product is. So, for instance, something that needs to be shipped, those last emails are usually sent sometime around the 10th or the 15th of December, because it’s that whole idea of getting it in time for Christmas.

Now, if you’re someone who offers gift cards, your Christmas season is extended, or if it’s something like an online gift, like an audible, anything that can be delivered electronically, those Christmas, uh, campaigns can actually go right up to, to Christmas Eve, and even, I would say, Christmas Day, because I don’t know about you, but, you know, I see a lot of family around Christmas. I always try to have gifts for the people I’m going to see, and it never fails, there’s somebody there I wasn’t expecting. So, it’s nice to be able to run back to your bedroom and, and, and get them an Amazon gift card…

[01:00:46] Matt Bailey: Yes.

[01:00:46] Jeanne Jennings: …and put it in an envelope so it doesn’t look like you’ve forgotten them. So yeah, depending on, you know, if you have to ship or if it’s an online gift.

[01:00:52] Matt Bailey: How is supply chain issues affecting shipping, retailers, how all this, are you seeing that affecting this holiday season?

[01:01:03] Jeanne Jennings: Yeah, it’s definitely an issue. Um, and it’s an issue in two ways. It’s an issue in getting things from international, which, I’m not sure I realized, I mean, I guess I knew, but I’m not sure people realized how dependent they were on international organizations.

[01:01:16] Matt Bailey: Right.

[01:01:16] Jeanne Jennings: ‘Cause, you know, maybe you’re getting the product from someone in the states, but they’re getting the chips from someplace else. So, we have supply chain issues on that end. We also, honestly, are, are, are probably going to see supply chain issues on this side with getting things delivered. I don’t know about you, but my Amazon deliveries have slowed down, you know, it used to be the joke, right? During the pandemic 2-day Amazon delivery became 2-week.

[01:01:40] Matt Bailey: Right.

[01:01:40] Jeanne Jennings: But you weren’t going to complain, ’cause, you know, it was just the nature of it.

[01:01:44] Matt Bailey: Right.

[01:01:44] Jeanne Jennings: But, but yeah, I think we’re running into that. I mean, one thing I think that retailers are much more prepared for this year than they were last year, I mean last year was just a big cluster.

[01:01:53] Matt Bailey: Right. Right.

[01:01:54] Jeanne Jennings: Um, so this year I, I, you know, with my clients, we’re talking a lot more about, “Order early before supplies run out,” you know, “Don’t get stuck not being able to get what you want,” so it’s nice because you know, we are always trying to introduce urgency into the marketing language. This is honest to goodness urgency.

[01:02:11] Matt Bailey: Right. Oh, wow.

[01:02:12] Jeanne Jennings: And they’re hearing about it on the news, and they know that we’re not making it up.

[01:02:15] Matt Bailey: Very true.

[01:02:16] Jeanne Jennings: So, I think that that is driving people to buy earlier, people who can plan. But yeah, that’s definitely playing in this year, but again, if you leverage it for your benefit with the urgency, I think it can actually be something that helps.

[01:02:28] Matt Bailey: Wow. Good. Good. Well, Jeanne, I have thrown a lot of questions at you, and look at you. You are still, you’re, you’re looking great. You got through it. Thank you so much for spending time with me today.

[01:02:41] Jeanne Jennings: Oh my gosh. Thank you for inviting me. Always a pleasure to talk to you, Matt, and, um, yeah, just have a happy holiday, now that we’ve all talked about holiday. Be safe, stay well.

[01:02:50] Matt Bailey: Alright. And Jeanne, how can people find you? I’ll put a link in the show notes, but in case they’re not on the website, how can they find you?

[01:02:58] Jeanne Jennings: Sure. So, uh, I blog at my, uh, company website, which is, my company is My website is a little shorter, it’s emailop, O P, Um, if you Google me, it should come up.

The first name is Jeanne spelled, J E A N N E, and the last name is Jennings. I’m also on Twitter at, @jeajen. And you can follow me on LinkedIn. So, um, yeah, just follow me there, I also am general manager of the Only Influencers, Community of Email Industry Professionals. So, I also, um, write for their blog, and then I have another company I’ve actually been writing for Webbula, which is and a lot of the things we discussed today, but not all of them, are actually going to be, uh, in a blog post that hopefully will be published there next week.

[01:03:48] Matt Bailey: Great. Great.

[01:03:49] Jeanne Jennings: Um, so yeah, definitely, uh, check that out, and if you have questions or you ever want to talk email, uh, just reach out. I’m always happy to do it.

[01:03:56] Matt Bailey: Fantastic. And yes, listener, I would highly recommend subscribing to Jeanne’s emails and the, the email Roundup. I’m going to put a link to that in the show notes, uh, because it, it’s not just Jeanne, it’s other email professionals, and the amount of information that comes out on that is just fantastic. So, it keeps you in mind of that email channel, which honestly, don’t overlook it. In fact, do the opposite. Invest. Invest in your email and what’s happening there. Jeanne, thank you so much.

[01:04:28] Jeanne Jennings: Thanks so much, Matt. Take care.

[01:04:30] Matt Bailey: Alright, you too. Have a great holiday season, and you too, dear listener. I hope this has been a worthwhile podcast and inspiring you to take another look at your email campaign and planning for next year. Alright. Thanks again, dear listener, and we’ll see you again on another episode of the Endless Coffee Cup.

Featured Guest:

Jeanne Jennings

Website: Email Op Shop
LinkedIn: Jeanne Jennings | LinkedIn

Only Influencers

Previous episodes featuring Jeanne:

Email Isn’t Going Anywhere

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