It’s Not Too Late: Your 2025 Black Friday & Cyber Monday Email + SMS Playbook - EP 53
In this episode of the "Send It" podcast, hosts Jimmy Kim and Chase Diamond deliver a concise, actionable playbook for e‑commerce brands that have not yet finalized their Black Friday/Cyber Monday (BFCM) strategy. They begin by reframing BFCM from a single‑day event to a multi‑week season, then outline three timing frameworks – Early Bird (early November), Core Week (Thanksgiving week) and Late Burst (Thanksgiving‑to‑Cyber Tuesday) – and explain how to choose based on inventory and cash‑flow needs. The duo presents four offer archetypes (discount drivers, value‑add, access‑based, community‑driven) and ties each to inventory or cash goals. They dive deep into email vs. SMS roles: email for storytelling and the “why,” SMS for urgency and the “when,” recommending cadence (2‑3 emails per day, 1‑2 SMS per day) and trigger stacks (email‑then‑SMS follow‑ups). A pre‑launch VIP/early‑access sequence, controlled closing cadence (48‑hour final‑hours series, last‑chance emails, possible encore), and post‑purchase retention flows (referral bonuses, new‑product launches) are detailed. Practical execution tips include building a calendar, segmenting frequency, and avoiding redundant messaging. Sponsor plugs for Kintsugi (automated sales‑tax compliance) and Omnisend (AI‑powered email/SMS automation) are inserted but framed as tools that can support the playbook. The episode wraps with a recap emphasizing early smart planning, organized execution, human‑centric messaging, and the view that BFCM is a springboard into Q1 rather than an end point.
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The reality is a good end of a sale could do just as great as a start of a sale ultimately. And most brands just say it's like sale ends tonight and then they disappear. But you should really control, like create almost a controlled landing curve when it comes to your closing. Let's say 3 days before your event is closing, you start sending some kind of like final hours or maybe 12 hours or 24 hours. You want to kind of set that final hours. Like I like to start at 48 hours. Then you also probably want to do that whole last chance email. Like there's a lot of ways you can drive it, but you want to think about it as a controlled landing Don't just shock them and surprise them and try to get them to push. Announce it and repeat yourself over and over again for multiple days as you come into that close because, well, people need that urgency to make that decision. Yeah. You know, this is our 52nd episode. I was just looking at the notes here, which means that we've successfully— actually, it's our 53rd episode. So we've successfully done a year of podcasts around email marketing and SMS marketing.
Dude, I did not realize that. Wow. Well, thanks for everyone tuning in for a year. Yeah.
Hopefully, we've got some people who have been listening since day one. That's awesome of you. If you did, I would say leave me a comment just so we know who you are. But otherwise, man, let's shoot this thing in 3, 2, 1.
From the open to the click, they're the masters of the flow. Just watch your list grow and your leads turn to go. Did we retain you so far or do we have to extend it? If you want results, you know you got to send it. Yeah. You know you got to send it. Yeah, you know you gotta send it. Yeah, you know you gotta send it.
What is up everyone? Welcome back to Send It, where we discuss anything, everything retention marketing, specifically in email and SMS marketing in e-commerce. My name is Jimmy Kim and I'm here with my co-host Chase Diamond. All right, Chase, it's that time of the year again and today we're doing our annual Black Friday Cyber Monday playbook and we're gonna Kind of do a playbook for brands that haven't planned yet. Basically, if you're watching, listening, hearing this thing and you haven't planned it, this pod is for you. And even if you've planned something already, I would say maybe you'll pick something up, but we're not going to get super deep. I think that's one thing. It's not too late, but we also, we also want to make sure that we're not making this complicated because time is an issue. And if you're listening to this pod right now, chances are We're like a month away. Chase, thoughts?
Yeah, I think the best way to look at this is, look, the window is closing. Um, it's going to be too late soon, but it's not too late today. We're going to give you the 80/20. What are the 20% of things that you need to do and that you can do this last minute that are hopefully going to drive a bulk of the actual revenue and performance? So the good news is if you listen to this, you can still win Q4. If you execute swiftly and kind of with a focus. I mean, we're gonna kind of walk through like a flexible, let's call it week-by-week framework for BFCM using both email and SMS. So how to start, how to end, and really how to keep the energy going, you know, through all the way into December.
Yeah, that's perfect. All right. So first let's start off with mindset because I think this is really important to kind of start and set the stage here. So BFCM or Black Friday, Cyber Monday isn't a weekend anymore like it used to be. I mean, it used to be something that, you know, we look forward in the retail side on a particular day and whatever it might be. But now I'd almost say it's a season. Now consumers start shopping right after Halloween candy goes on clearance sale.
And, and maybe even just as soon, right? Like, you never know. Every year at some point, right, the joke is going to be it's starting in July, right? Or starting in August. Who knows? And, you know, the Shopify data shows that over 60% of BFCM purchases now come from customers who first engage before the week of Thanksgiving. So if you're starting on Black Friday, you're already playing from behind.
Oh, totally behind. So let's go ahead and start kind of defining that framework. You called it the flexible start framework, and it really boils down to 3 different options depending on your brand inventory and kind of your demand curve. So I would say that there's approach number 1, which is like the early bird. And these are people starting November 1st, November These are best for brands with heavy inventory or a lot of repeat buyers, something that people are constantly building. And the big thing I would note here is that you want to build momentum and with cash early, and it prevents like the fulfillment bottlenecks that you might create for yourself. Then you've got the approach number 2, which is like the core week. I'm talking about Monday of Thanksgiving week. So you're giving yourself almost a full week ahead of time and going into it. This is best for most balanced brands. So the majority of brands are going to find the most effectiveness here where you're going to have urgency while still setting yourself up for success. Staying relevant at the end of it. And then the last one I would almost call the approach is like the late burst. If you've got a brand that's limited luxury, high margin, you guys just sell in scarcity, well then you should be running literally a Thanksgiving Day to Cyber Tuesday, I think is now the new marker here because you basically went on scarcity and exclusivity at this point.
Yeah, and I'd say like the real point that I feel like you're getting across is just pick a lane, right? You know, early start means you can ladder in kind of soft drops and VIP type access. However, if you're kind of late to the game, you better bring the creative firepower as soon as possible.
Yeah, no, you're totally right. I think there is no wrong answer. It really just depends on your bandwidth and your business.
Hey, it's Jimmy. Quick 15 seconds of your time because I have something fun to share. Did you know between the two of us, Chase and I, we have over 20 years of experience in email marketing? Recently, we put our minds together to create a certification program that takes all of our knowledge and share it to the world. It's called Ecom Email Certified. It's an end-to-end course certification program that's designed to take anyone, regardless if you're a newbie or an experienced marketer, founder, executive, agency marketer, or any marketing professional, to teach them everything we know about email marketing, SMS, from deliverability to AI to copywriting to design to strategy. We cover it all. It's loaded with 175 modules and 25 hours of education combined with quizzes, community, All designed to educate, test, certify you to become a full-fledged email marketer for e-commerce. And so as you're listening to this pod, we want to reward you with loyalty by giving you a coupon for $200 off this certification. Just jump over to ecomemailcertified.com, check the show notes. Now back to your pod.
Chase, let's talk next about strategy a little bit. Everyone does 30% off statewide, but I think differentiation is everything. What do you think about, man?
Yeah, so there's kind of like 4 offer archetypes that I think we both kind of agree on. The first would be kind of like the discount drivers, which you're kind of alluding to, you know, some kind of percentage off. But there's also things like a tiered base spend, or even just doing like discounts through product bundles. That's number one. The second would be more like value-add offers. So tossing in like free gifts, any kind of like shipping upgrades, and even things like extended warranties. And then the next one is what we consider to be like an access offer. So early access for subscribers, secret drops, VIP windows, etc. And then the last one is more geared towards like community. So it's a community-driven offer where there could be things like, let's call it like a charitable tie-in, or maybe even like a member-only, community-only type collab.
Yeah, no, I like that. Those are 4 solid ones. And I think the key ultimately is aligning offers to inventory and cash goals. I think that this is something as a retention marketer or a founder or whatever you are, you know, this is your opportunity to kind of get rid of some of this stuff and also put it on sale. So if you're overstock, bundle and clear, right? Put as much together as you can to bundle. And it's got to make sense. You can't put socks with like, with a t-shirt on. It doesn't really generally make sense, but socks with shoes or something might work out. If you're inventory tight, you should also use early access and waitlist scarcity. 100%, you want to take advantage of that early small scarcity. But if you're cash hungry, right? I think what I like to see is that you would do a tier discount really to focus on driving AOV, right? Spend $100, get 20% off. Spend $200, get 30% off. That's probably how I'm thinking about this.
Yeah. I think the best way to start isn't just a kind of blanket discount type blast. It more gears towards like warming up your actual list.
Yeah.
No, I would 100% say you definitely want to do kind of like a 3-step like pre-launch. So like one, obviously use email and SMS. You want to hype them, tease them, hint at the exclusivity, so forth. And probably do some kind of VIP access where you let the customers first and like maybe people are raising their hands. So even before prospects, you might want to split that up and say, hey, if you're a customer and you want to get on this VIP list, we have a special portal, really just because, you know, this is where your bread and butter comes from. And then of course you've got like your broad public launches when like your website and everything, your ads, everything shows up and it's a very clear offer and offers extreme urgency as well too.
Yeah. Yeah, exactly. And remember, inboxes explode that week, right? So, you know, getting creative in terms of, you know, the timing and, you know, the content and the subject lines and everything's super important. So sending VIP drops, let's call it like early morning or kind of off-peak hours, like a 6:00 AM to 8:00 AM local time type thing, is probably a good way to start.
Yeah. And, and just to add to that, you know, When I talk about the VIP list, you know, you want to get really clear with this. Don't try to get sneaky with it. Subject lines like you've earned it, early access, you know, things like that. Things that make people feel like they're getting an early access is really important and you want to be direct with that.
Yeah. And as you're talking about this, one thing I was just thinking about is I think one of the biggest missed opportunities with all of this is actually how you end your sale.
Totally. Dude, I love a good ending of a sale because the reality is a good end of a sale could do just as great as a start of a sale ultimately. And most brands just say it's like sale ends tonight and then they disappear. But you should really control, like create almost a controlled landing curve when it comes to your closing. And the way I think about it, right? You're thinking about downslope, you know, maybe day 1 or, you know, let's say 3 days before your event is closing, you start sending some kind of like final hours or maybe 12 hours or 24 hours. You want to kind of set that final hours. Like I like to start a 48 hours because that's relatable. 48 hours left and an SMS reminder. Then you also probably want to do that whole last chance email. If you want to extend it for VIP, you can do that as well too. So like there's a lot of ways you can drive it, but you want to think about it as a controlled end. Don't just shock them and surprise them and try to get them to push. Announce it and repeat yourself over and over again for multiple days as you come into that close because, well, people need that urgency to make that decision.
Hey, it's Jimmy, and I hope you're enjoying the pod so far. I want to talk to you about one of our sponsors, and it's about sales tax. Yeah, I know nobody wants to hear about it, but here's the thing. You're selling online. You've probably spent way too much time, money, and stress on something that should be automated. Enter Kintsugi, pronounced Kintsugi, named after Japanese art of turning broken pottery into something beautiful and resilient. That's exactly what Kintsugi does for your tax chaos. Their AI monitors and files and optimizes your sales tax automatically across all states and jurisdictions. They even go to Canada and even to Europe as well. We're talking about saving you serious time. The average customer spends 9 hours every single month working on this. That's over 100 hours a year that you get back to focus on your actual growing business. But here's where it gets really good. No more expensive tax professionals eating on to your profits. Kintsugi AI handles compliance with a 98.3% reduction in error. That's practically bulletproof accuracy. One-click integrations with your existing platforms and systems mean that the setup is painless, and their white glove support team has your back every step of the way. Sales tax headaches? Gone forever. Consider them eliminated forever. And it's e-commerce, SaaS, and agency— anyone who pays sales tax needs Kintsugi. And we have a very special offer for you today. If you mention Jimmy and Chase, you get 3 months completely free. That's 3 months of automated tax filings, perfect compliance, and getting your life back. Visit trykintsugi.com and mention Jimmy and Chase for a 3-month head start.
Yeah, that encore is kind of an interesting one where if you do it the wrong way, it just kind of seems like you're not focused on keeping your word. But if you do it strategically and it's for specific groups and for maybe a specific reason, Dude, it could drive like 10 upwards, maybe even 20% of extra revenue. Because it's that FOMO where it peaks after the people think that they've already missed it. But again, you do have to be strategic here. Or else maybe it can bite you.
Yeah.
And it's not just like FOMO. It's also people are traveling and different things that happen because it's also a crazy time of the month too. I know myself, I have like family over and like all sorts of— last thing I'm doing is watching brand emails. And I don't have any participation in Black Friday. So I'm going to Just like you, Chase, we're going to clearly just take the day off because it's either you're online shopping or you're offline because you're not trying to spend. And I don't know about you, Chase, but I'm in a non-spending mood these days just because of all the house crap going on. So, um, Yeah. But to go back to that whole FOMO thing, you know, the thing I'll add to that is just make sure the reason is believable. Extended by popular demand, system overload, warehouse extension, something authentic. Urgency is so much better than fake urgency. You know what I mean?
Dude, 100%. Um, and I think like it'd be important for us to address the question we always get is, does Cyber Monday even matter anymore? What do you think?
Cyber Monday is an interesting one because I think it still does, but not in the old sense. You know, back in the day, Black Friday was your like mass sale and then Cyber Monday was like your, uh, like your, uh, internet sale, right? It was like your retail versus internet sale. But now The way I almost look at it is that Black Friday is your like mass sale and like your mass generic market hitting prospects and everything. Cyber Monday is almost like your retention moment. It's like your time to almost make your second sale or take all those customers and they're waiting because they're waiting on the sideline for that different deal and whatever it might be.
Yeah, I think that's spot on. I'd say really just, yeah, you use Black Friday to acquire and convert and use Cyber Monday to upsell, cross-sell. Ultimately extend the relationship.
Yeah, no, you're right. Example, Black Friday, 30% off everything. Cyber Monday, buy more, get more gift cards or free add-ons for loyalty members, or, you know, you know, whatever it might be, buy one, get one free. I think you can take the same idea and position it or whatever it might be.
Yeah, 100%. And to your point, you could flip it as well, right? Using Cyber Monday to clear final SKUs with deeper discounts on any kind of leftover type items.
Yeah, and one of my fun playbooks that I always talk about when it comes to Black Friday, Cyber Monday is launch a new product. You've got the most eyes and vision on your site.
Yes.
You can launch a new product at full price, even if you're giving discount on everything else. It's definitely been a playbook that I've used in my past. But let's talk about this orchestration side of things because I think what's important is email and SMS, they kind of play a different role when you walk into this type of the holiday, right? I think in the email, it's more story. Yeah. It's visual. It's a morning time or off-peak hour. And it's very much like your access starts Your VIP access starts right now. Where SMS is going to play a really big role in Black Friday with urgency and reminder, 3, 4 hours after the email or like the last few hours of the sale, it's ending right now, shop now before it's gone. You know, I feel like there's a difference there.
100%. I think thinking of email like as the kind of long form, more information, it's best to think of it as the why, whereas SMS being kind of tied to urgency and more short form. It's more thought of as like the quote unquote when.
Yeah, no, I love that. That's exactly spot on. And, you know, another thing I remember as I'm thinking about all this is you want to segment your frequency, right? Look, this is probably the one time of the year that marketers are forgiven for sending a lot of emails because consumers are looking for it. They want to know about the deal. So sending 2, 3 emails per day during core BFCM is fine as long as each one has a good unique angle. I think that's really there. Now on SMS, I think I'm thinking about more max 1, maybe 2 per day, really focused on those like impact windows. Kind of what you said, that when is more important than it is the why at that point.
Yeah, 100%. And I think with that, keep in mind you can also stack triggers. So send an email. If someone doesn't open or doesn't click, send an SMS follow-up reminding them that their cart or their discount, whatever it might be. Um, is expiring soon type of a thing.
Yeah. I mean, that's a perfect thing you can set up right with our, uh, partners over at Omnisend. You can do something just like that. So that's a good one to think about as well.
Hey there, it's Chase here. I hope you're enjoying the pod, but I wanna get just 30 seconds of your time real quick to tell you about one of our sponsors who let us make this great podcast. So first I wanna start with a question for you. Do you ever find yourself staring at a blank page waiting for inspiration to strike? Your marketing campaigns don't have to suffer when your creativity runs dry. Omnisend has recently launched their most powerful AI update yet, and it is awesome. Its AI completely transforms how you can create and send your next marketing messages. And here's really what's incredible: their AI doesn't just write your emails, but it actually helps you write really compelling subject lines, preheader text that are geared to increase your open rates and ultimately build customer segments in, in a heartbeat. And just whisper to the AI who you're targeting and it's gonna figure out all the complex segmentation for you. So that way you have no more guessing games. But hey, wait, it gets better. Their AI writer actually now proactively suggests improvements to your copy and it's gonna adapt to your brand's unique voice and tone while following email marketing best practices. And their personalized product reminders analyzes your browsing behavior to serve up exactly what each of your customers wants and needs to see. And their campaign booster automatically resends emails to people who didn't open or engage with them, which helps lift revenue by an average of 13%. And now with over 150,000 very happy customers already dominating their markets using Omnisend's email, SMS, and push notifications. Plus they have 24/7 amazing support that actually responds fast and is very helpful. You're joining a winning team. So stop wrestling with writer's block and start letting AI do the heavy lifting for you. Visit omnisend.com and experience the future of marketing automation. Let them know that Jimmy and I sent you. And now back to the pod.
Look, Chase, all of this means nothing if it's not tied to business goals. I think I wanna make this really clear, and this is a really important thing for a lot of marketers and founders and operators listen to. If you need cash flow right now because it's been a tough year for some people, push early, early access and push bundles, right? If you have just tons of inventory, I've had this problem before, inventory clearing where you just need to get rid of a lot of stuff. It's taking up space, it's taking up space at your DPL, whatever it might be, run an escalating discount, right? Across the week, try to find out ways to do it. And look, if you want retention growth because of all this stuff, I think this is where you create post-purchase flows immediately. Here's how to use your new product plus a referral Bonus, anything you can do to get them to come back to make that second purchase with you because that's really it. BFCM is a funnel clearing product thing, but your next job starts right away. So you're funnel clearing all the prospects that have been coming through your funnel for weeks on weeks and months on months. And then you're also starting your retention activity, which is now that I got them to purchase, the real AOV or the real dollars come in on my second purchase and I need them to get that second purchase done.
Thoughts?
Yeah. So well said. I'd say BFCM isn't the end-all be-all. It's not necessarily the finish line. It's really more of the springboard into Q1, and you can put yourself in a really kind of great position to do that if you leverage pretty much everything we talked about today.
Yeah. So quick recap, man. And I feel like we did a good job kind of really slimming this thing down. So one, start early as you can, but start smart regardless, right? Make sure it makes sense with your business and your marketing team and all that stuff. Design offers that fit inventory and cash flow. So don't just think about 30% off. Think about, How can I do well for my business while giving the consumer a good deal at the same time or perceived good deal, right? And this is where— why I say launch a new product. Plan your start, end, and encore. Dude, this should be a calendar, right?
Yeah.
Like start, this is my date, this is what I do. That way you can really plan all your moments that come into place. And then you want to use email and SMS together with purpose, not as redundancy. The last thing you want to be thinking of as redundancy, it's the same human on the other end and chances are they're going to get more of those SMSs. Then you really care to know how much they're getting. I know as a consumer, I get a ton of them. So make sure you're using them with purpose. And last but not least, I would say the thing that we recapped was using Cyber Monday to as a more of a retention moment, not a rerun moment, right? How do I get them to make that second purchase? How do I get old customers reactivate? Not how do I rerun my Black Friday sale?
Love it. I'd say like the biggest takeaway and the last thing for me is like, I think to summarize this, like the brands that are going to win this BFCM They're not going to be the ones that are kind of the loudest or trying to make the most amount of noise. They're going to be the ones that are A, the most organized, and B, the most kind of relatable and human kind of in their messaging and their approach.
Yeah.
And if you take anything from this today, it's not too late. It's not too late to change things. It's not too late to re-architecture things. There's time, but you still need to make sure you're planning. And I think the key here is if you know how to plan and schedule, the rest of it kind of falls back into place. It's really not that hard and don't overthink it. So, you know, my advice is execute with clarity. Clarity, but stay nimble because if it doesn't work, you got to be ready to pivot just as much too. Any closing thoughts, Chase?
No, nailed it.
Yeah, no, dude, I think this pod wasn't super long, but it's very intentional because we're expecting you to be very busy as you're listening to this. So we hope you can kind of take this, take these shortcuts, take these tidbits and make some moves here with your Black Friday, Cyber Monday. With that, dude, it's a wrap. This is a wrap for our Black Friday. I don't even know what we're going to call this thing. Maybe just like the Black Friday, Cyber Monday Ecom Playbook. I don't know what we'll call it. Pretty simple, but We're covering all the important things that you need to do. So if you enjoyed this podcast, as always, give us a thumbs up, subscribe, follow, leave us a rating. You can follow this show on X, LinkedIn, YouTube Shorts, IG, TikTok, etc. But we are on YouTube primarily. And there's a few ways to connect with us. Number one, you can join our community or our newsletter. You can learn about that at ecomemailcertified.com. Links in the show notes below. Secondly, you can join our newsletter, ecomemailmarketer.com. Where you can kind of get our daily newsletter on retention that we send. And then of course you can follow us on social media personally as well. Chase, they can find you literally everywhere. Chase Diamond, no A in Diamond. I got this now. And then you can find me on LinkedIn and X today. With that being said, guys, thanks for tuning in as always. Keep sending it and we'll see you next week. Adios.
Cheers.
From the open to the click, they're the masters of the flow. Just watch your list grow and your leads turn to go. Did we retain you so far, or do we have to extend it? If you want results, you know you gotta send it. Yeah, you know you gotta send it. Yeah, you know you gotta send it. Yeah, you know you gotta send it.
