The Tips You Need for Black Friday/Cyber Monday Email and SMS

0:01Hello and welcome to Shopify Masters, your companion for starting and building a business. I'm Adam Levinter. The holiday shopping season is almost here, and that means your inbox is going to be filled with sales and new products from your favorite brands. You might even get text messages on your phone about Black Friday deals. A lot of companies are working on those marketing materials right now, so we brought in an email and SMS expert to discuss all of that with us today. Jacob Sappington is the Director of Email Strategy at Homestead. It's a growth agency based in Wisconsin. He's worked alongside some giant DTC brands, including Hexclad, Casely, Brightland, and more.

0:38Jacob is here today to help you figure out how to get your customers excited about opting into marketing communication and what strategies he's recommending to his clients for the holidays and beyond. Thanks for joining us, Jacob. Welcome to the show. Thanks for having me, Adam. Okay, Jacob, so you're at Homestead, which is a retention conversion campaign management agency. You're overseeing a ton of brands in the DTC e-com world. I was just wondering, how did you get into this space? How did you become this DTC email marketing guy? Yeah, so a couple of years back, I was the manager of retention at a holding company called 4x400.

1:14I'd been there for a year. We had five brands. At the time, I had my sights set on opening up my own agency. And I knew Zach and the Twitter community that I'm a part of. Zach's the founder of Homestead. And I reached out to him. I said, Zach, you know, I'd like to start my own agency. Do you do any consulting? Because at the time, and still today, Homestead had a really good reputation as like this up and coming agency. And so I said, Zach, I know that you've had a lot of success here. I'd love to book a consulting call. Do you offer this? And he said, no, I don't. But I have another idea that we should talk about.

1:43And so I reached out to him trying to learn more about, you know, how to run an agency, agency ops, all that stuff. And then he pitched me on why I should join Homestead. And so it was a really, really hard decision and one that I'm really happy that I went with.

2:02That's a great story, actually. And you're still there. So proof is in the pudding. So plenty of brands are ramping up marketing efforts heading into Black Friday. And thinking about the proper execution of these upcoming promotional campaigns, sequences, and we will get into the weeds on all this stuff during this podcast. but from a high level, what are some of the best practices merchants should start with? Yeah, I mean, the big thing here would be focusing on your list growth. You should be focusing on it prior to this timeframe, but it's also a great time whenever you see this huge influx in traffic to be focusing on that list growth component.

2:38But then also just accepting that like during this timeframe, you can be a little bit more aggressive with your campaign sends. You can send to a broader audience and not trying to take it too refined. Like I think some people segment too fine and they're leaving out people who are on their list that they could potentially sell to as well. So when you say merchants can get more aggressive this time of year, are you talking about the number of emails that a merchant could send during a sequence or during a campaign? Yeah, I'm talking about the number of campaigns that get sent, but also the number of people they're sending to within those campaigns.

3:13For example, we're recommending for all of our brands to send three emails on Black Friday, multiple emails on Cyber Monday, multiple texts on Cyber Monday as well. And so throughout the rest of the year, we're not recommending for brands to really double up on multiple emails a day to the same people. But during this timeframe, one, we're dealing with increased competition in the inbox. And so to stand out, we kind of have to, but also the volume of people as well. So like during this timeframe, we're ramping up our segments. So if normally, like just as an example, if we were going with like 150, 180 day engaged segment, maybe we're pushing that up to like 165, 180, 210, 10, seeing the bounds of like, how broad can we go without hurting our deliverability?

3:51And then even like leading into like BFCM, it's like bringing in like BFCM purchasers from last year, the year prior, maybe taking those engagement segments even further. It really depends on like how big the brands, the size is, but for like smaller brands, I would, I would definitely encourage them to, to effectively go like full list send with some like, um, some proper exclusions in there around purchasers, some like unengaged criteria, but for the most part, like being really aggressive with who you're sending to. The phrase that I frequently use with our team, with our clients is that we send reputably like 362 days out of the year, so that for three days out of the year, we can be a little bit crazy.

4:29So again, like leading up to this, it's really important for us to maintain our deliverability and make sure we can stick in the inbox with these users. But then once we get there, it's definitely a much more aggressive play. So when you say maintain deliverability and stick in the inbox, is this because you're finding that a lot of emails end up in the spam filters or get caught there? Like, how do you warm up a list? How do you maintain that sort of whitelist status? How do you get into that inbox? So if a user has Apple privacy features enabled, effectively what happens when the email comes into their inbox, it's automatically opened.

5:02And currently we don't have the ability to distinguish a bot open from a real open with 100 % accuracy. What systems do now, as I say, if a campaign is open within seconds of its sending, that signifies bot behavior to us. And so what happens is a lot of brands aren't segmenting these attributes out until they get to where their open rates are just incredibly inflated. 60%, 70%, 80 % open rates. It's just incredibly dirty data. And people who are in their accounts think they have this really high open rate when in actuality they don't. And so what we do is we use that segmentation to have a cleaner picture of where our open rates lie.

5:36And then once we do that, we're really looking for our open rates to stay in the 35 to 40 % open range. If a brand's hitting 35%, then I'm starting to get concerned because that's probably pre iOS 15 is probably more of like a 20 % open rate, maybe, maybe lower than that. And so the tricky thing about deliverability is that so much of it is kind of, you know, best practices of the industry. We don't fully know what leads to people getting in spam across the different inboxes. And so there's there's assumptions that we have to make. And so one assumption that we're making is that when we're dealing with this clean data set, that a 35 to 40 percent open rate keeps us in the inbox, keeps us from getting flagged as spam.

6:14And so, yeah, the intent there is maintain deliverability in a way that we're confident that we can send to enough people without hurting our ability to get into the inbox. And that's the most revenue that we can. So you mentioned two things that I just jotted down I want to double click on. The first is segmenting out properly. The second being getting clean data. Is this a question of just using the right system? For example, you mentioned Klaviyo. is this the system to best segment one's data and to get to clean data? Is there another strategy or tactic here? I would say that Klaviyo represents a great solution for this.

6:57They are an ESP, but really more than anything, I kind of view them as a data platform that ingests data from a bunch of different sources. You know, obviously they have a deep integration with Shopify. And so we're able to get down several layers deep into the metadata to understand that piece. We can bring in data from any number of review platforms, from help desk platforms. And so because it is able to ingest that data so cleanly, it does make a great solution for a lot of brands. The big thing with the clean data is just filtering out people whose only engagement with us is that Apple privacy open.

7:30And so the way that we approach this is that we have many criteria that we determined to be engaged. So it's anything from like someone who just recently signed up, being opens, clicks, being on site, doing products, signing to cart, starting a checkout, all these different factors that we take into it. And what we're saying is that if someone's only engagement with us is this bot open, then we don't want to include them in our engage segments.

7:59The flip side of that is that there are real humans on the other side of that who will eventually click and purchase if we give them the opportunity to. So we're trying to balance this blend of segmenting cleanly while not engaging with people who might not be actually engaging with us. And so one way that we work around this is that once or twice a month, whatever we deem to be the most high intent campaigns of that month, maybe it's a sale launch, maybe it's a sale last call, maybe it's a product launch. We are open to bringing in those users who are only showing us bot traffic or who are only showing the bot opens.

8:36And so that allows us, again, to make sure that we're not losing out on revenue, because, again, there are users on the other side of that that are engaging, but we just can't currently tell to what extent.

8:49when you are looking at some of the merchants that you are supporting as an agency what are the biggest mistakes you see some of these e-commerce companies doing when it comes to email marketing both with respect to black friday and also in general yeah i would say for black friday the the biggest thing is just not enough emails just not being aggressive enough which is kind of that piece I touched on earlier. So not being aggressive enough, both in terms of volume of campaigns and the total number of people that they're sending to. In general, we see the segmentation issue a lot. Like a lot of times we'll see brands who have great looking emails.

9:29There's great copywriting behind it, great design. The thought process behind them is well thought out. And then you look at it and they're sending to like a 30-day engaged audience. And so our thought process on this is that we want to send as broadly as we can without hearing those deliverability KPIs. So with that being said, like if you're only saying to like a 30-day engaged audience, you're inflating your rate numbers. So like your open rates, your click rates, your place order rates, all these rates look fantastic because you're only selecting the most engaged people. But on the flip side of that, if you think about it, there's tons of products that we buy every single day that we don't consume on a 30-day basis.

10:06And so by filtering out those users, we're missing out on dollars of like users that we've already acquired once. And it's the whole reason why email is so powerful is because it's a much cheaper delivery platform, a much cheaper distribution than other forms, including SMS, including paid ads. And so if we're segmenting so refined that we're excluding these people, we're losing out on dollars. We're losing out on a really effective form of communication with these users. So you mentioned SMS. We're seeing the rise of this as a viable channel for building on the customer relationship. In your view, is SMS an acquisition strategy or is it better utilized as a customer nurturing tactic once someone has actually purchased something?

10:51Yeah, I lean much more on the acquisition side. And the way I look at both email and SMS channels is that they're an own channel, but they're also a dependent channel. And so paid ads, paid search, paid social, organic traffic, all the different ways that people get onto your site, that's how they're getting onto your email and SMS list. And so these should be multipliers of your acquisition efforts. A really recent example, we work with this company called Dose. When they came on, they had a really poor opt-in rate. We helped them improve their opt-in rate. It doubled their rate of list growth, which allowed them to increase their paid ad spend, which became a flywheel.

11:27I think over a certain time frame, I think we 4X their daily users that they were opting into their email list. And that's huge in Q3 because we're immediately going to reap those benefits in Q4. but it's something that we should really look at across the whole entire year. I'm chatting with Jacob Sappington, Director of Email Strategy at Homestead Studio. I hope you're enjoying our conversation. And if you haven't already, please subscribe or follow Shopify Masters wherever you get your podcasts and leave us a review or feedback for the show. It helps our audience find us. Thanks so much. Jacob, if you were advising a B2C e-commerce startup and the challenge here was how to best build a funnel, and how to best build your list.

12:11What strategies or tactics would you suggest that they implement first? I mean, start collecting right from the start. That goes for email and SMS. Even if you don't plan to launch an SMS program today, at the bare minimum, you should be setting up some form of collection for both email and SMS, set up in a way that doesn't hurt the conversion of the other. So tactically, we do that by setting up email on one page of a pop-up and then SMS on the second page of the pop-up. And then once you've got those users coming into your CRM, setting up the bare basics, like a welcome series, a browse abandoned, an abandoned checkout, and like a post-purchase sequence.

12:48Like four different flows where you're collecting people at the moment of user acquisition onto your list with that welcome series. It's going to be your broadest flow. And so you're just looking at it from a top-down approach. It's the flow that like adjustments to can have the biggest impact across the rest of your business. And then you're also collecting those bottom of funnel users and that abandoned checkout. but oftentimes for a lot of brands, this can be a really, really small portion of their audience. And so bringing in that browse abandon, which is just based off of like a viewed product trigger.

13:15So like looking at a certain item brings in a slightly lower level of intent user, but a higher volume. And so like, those are like the three main pre-purchase flows that I'd want to see them set up. And then the last one being that post-purchase sequence, setting the expectations, teach them how to use your product, teach them how to care for your product, whatever it is. A lot of times retention is directly driven by the product itself, but on email that's a mess. We have this opportunity to talk about just anything you need to know about your product that helps them use it better and increase their likelihood of repeating.

13:45Okay, so we'll talk about sequences more in just a sec. Collecting an email via a pop-up versus collecting a cell phone number. I think there's a lot of merchants that may not have perfect clarity here as to how best to capture a user's cell phone number versus an email. Email seems to be ubiquitous. I mean, most merchants understand how important that is. But on the SMS side, I still think there's some ambiguity about how to best capture a customer's cell phone and how to market to them. Can you just describe that in more detail? Yeah, so a major component of like list growth strategies for us is like the actual build behind the pop-ups that we're setting up.

14:28And this directly affects SMS. So we're looking at what we call a micro yes, where we're asking someone if they want to receive the offer prior to us asking them to input their email. Then we're asking them to input their email. And then the next step is SMS. Again, separating those two steps out. So on that SMS page, we're communicating the same offer. We're giving them the option to not opt into SMS if they don't want to. But if we make it optional, we see on average like half of the email subscribers end up subscribing to SMS.

15:03One thing that I wanted to double click on because I think it's an interesting concept for a lot of these Shopify merchants is this idea of a micro yes. So I would assume that a majority of brands don't use this micro yes strategy. They just go right for the jugular in terms of asking for the email. What is a micro yes? Yeah, so it's another page before you say enter your email here. It's just something as simple as saying, do you want 10 % off? Or maybe something like, what are you shopping for today? And then having some options for like different categories or collections that you have. The main idea here is that you're asking like a really small leading question that someone's really likely to say yes to, and then it gets them bought in a little bit.

15:50We utilize this for, I think, probably every single brand that we have. But the question that we get asked is, are you sure it's not just people who are clicking yes, who are showing up as like increased opt-ins. And we've tested this time and time again. We've back-checked the actual emails coming in versus the volume that the analytics say. And each time we see that, yes, it's the people who complete that second step, who actually go ahead and enter their email. And so as marketers, we're taught that the more steps we add, the less conversion we have. But this runs completely contrary to that.

16:20And it says we add a step and we get additional conversion rates here. Klaviyo continues to gain market share. They went public in September. They sit at about a$7 billion market cap, I think, at this point. But other folks might be interested in understanding what separates Klaviyo from MailChimp from some other systems. You did mention the connection and ease of integration with respect to Shopify, but is there a type of company that is best suited to use Klaviyo versus some other system or tool? yeah i would say like highly e-commerce focused um that's like the biggest extinguisher for me like i would say like the difference between like a klaviyo and mailchimp is pretty pretty night and day i mean mailchimp also just released their own sms product i haven't been able to check it out myself but um segmentation abilities integration abilities list growth abilities klaviyo really laps the field on email um on sms they're catching up to who i deem to be like the the top two like feature-rich platforms of Attentive and Postscript.

17:23And so they're making headway there. Okay, so let's get back to the sequences. So a lot of brands don't necessarily know how to best craft a welcome series, for example, and how a welcome series might differ from a customer nurture series or some other type of series. There's lots of questions about how many emails should actually be in a welcome series. Some marketing experts suggest that a welcome series should have, say, four to five touch points over a span of 15 to 25 days. I don't know if you agree with that or disagree with that. What do you recommend? Yeah, I would say the general framework of like four to five emails over a one to two week timeframe is a good base level to start with.

18:05The biggest thing is just like reading the engagement, reading the data. If we see a brand on the fifth email still has a 3 % click rate, and they're still getting engagement, they're still getting place orders, then by all means, extend it. Like your product probably has like a longer purchase consideration window and you should be messaging that out over a longer timeframe. On the flip side though, most brands see two pretty key moments in the welcome series when someone opts in. So again, it's that acquisition of someone saying that I'm coming from paid, I'm coming from organic social, I'm getting onto your email list for this offer, I'm purchasing right away.

18:40So that's like the major spike that you'll see in a welcome series. The other one will most often be whenever you're kind of reiterating the offer or perhaps trying to put some constraints on the offer. Like, hey, just as a reminder, your offer ends tomorrow or your offer ends today. Or maybe there's an offer upgrade in there as well. But for the most part, a lot of the brands that I've personally audited is that you see like a major spike at the beginning, which makes sense. And then a spike at the end as well. You should still be communicating the offer in every single email. whether that's just like introducing the founders, doing some more product exploration, talking about why you're different than your competitors.

19:13The offer can and should still live in all those marketing messages, but just naturally you're going to see the best performance out of the first email and then kind of whenever you reintroduce a higher level of urgency. What about the design of these emails? So you did mention, you know, merchant could have this incredible design and copy, but still the email won't get the open rate that they desire. lots of questions about how to create sections within an email, how many sections, the use of graphics, videos, text, how much text, the use of call to action buttons. Again, how many CTA buttons are most appropriate?

19:51What can you share? Yeah, we try to keep a pretty simple approach. There's this thought in email marketing community. It's like one email, one objective, one CTA. So we tried to stick to that. The idea is you shouldn't go from like, shop this collection to check out our charity work, to check out what our founder's doing. And that's like a newsletter format where that's kind of expected. You should keep a cohesive thought. And if you have multiple thoughts that are rambling into an email, you should separate into multiple emails. But the big thing is we design using Figma. We take image slices, we export them, we compress them, we drop them into Klaviyo.

20:28what this allows us to do is it allows us to control for brand better. I'm not sure if you're familiar, but custom fonts are incredibly fickle in email inboxes. And I would say for the bulk of our clients, Gmail makes up 50 % or more of their audience and Gmail doesn't allow custom fonts. And so you're from the start already running into an issue of like, how am I going to render in the inbox? Is my brand going to be represented in a way that I don't really want it to be represented? And so by using image slices and compressing, we're taking a small hit in terms of deliverability. Again, deliverability is kind of like this black box that no one really knows everything about.

21:01But the thought is that live text helps you get into the inbox better. But what we believe is that the tradeoffs by rendering correctly how we expect it to render, by being on brand, by being able to introduce other design elements that you can create in Figma that you just can't create in a live inbox, we think that outweighs the concerns on deliverability there.

21:24you did mention something that i find really interesting which is this idea of this mishmash of topics and maybe it's best to have an offer plus some sort of charitable initiative that the founder is involved in as part of a newsletter but not necessarily part of some other type of email when i was doing some research before this discussion there's sort of like five key messaging strategies, I want to say, that most brands are using with respect to email marketing. And I just want to highlight some of these and we can discuss them. One is personalization, two is emotion, three urgency, four social proof, and five storytelling.

22:06My question around this is, are there certain types of messages that move the needle on open rates more than others? For example, seems like consumers are a bit tired of the urgency promotional fodder, like get it now before the price goes back up or get this discount within the next few days. Is this the case? Is it not the case? What are you seeing? As long as a brand doesn't take advantage of it, we see that offers, sales, products, like those kinds of launches perform exceptionally well. The other piece around that is that we're, for the most part, very intentional about our subject lines around sales.

22:44And so even if we are accepting of a lower open rate, we're expecting that the people who are opening that email know what they're getting into. And so an example would be like, hey, third-person off-site wide sale starts now, something like that. There's no ambiguity there whatsoever. You know what's going on in the email before you even open it. And so even if we do expect a lower open rate, ultimately we care about driving revenue and driving business impact there. Yep. That totally makes sense. This idea of subject line intentionality, I find is quite interesting. Are there best practices here around how to get the most out of your subject line?

23:28Yeah. And the challenging part here is that due to the iOS 15 features we talked about earlier, it's just really, really difficult to A-B test subject lines anymore. Like if I A-B 70 % Apple privacy open users and 30 % Apple privacy users in the B section. And so I feel like you should have to take every single subject line with a grain of salt.