Week 24 - Amazon Prime Day is Coming, Plus Shopify's $3B Buyback, AI Shopping Tools, and Logistics Moves

MaxWelcome to The Checkout Point, your quick dive into this week's e-commerce buzz with me, Alex, powered by Bizcommunity. These 20 minutes pack the latest trends, news and insights. Let's navigate the digital marketplace together. Ready? Let's go.

RachelWelcome back to The Checkout Point. We've got a packed episode today.

Speaker 3Seriously packed I was looking at the rundown and I was like okay buckle up Three

RachelRight? So first up, Amazon Prime Day. June 23rd is the date. And according to Bizcommunity, Amazon just launched Prime in South Africa at R59 rand a month. That's like $3 and change.

Speaker 361 yeah and this piece from Ayodeji Adegboyega over at Business Insider Africa Had some good context on what that means for the local competition there.

RachelWe'll get into all of it. Plus, here's the thing. Sarah Mahoney's reporting that this year's Prime Day is leaning heavy into grocery deals. Like, that's a pretty notable shift.

Speaker 3Yeah, with what people are paying at the pump and the checkout line, that actually makes sense strategically. We'll dig into the numbers.

RachelThen we've got Shopify. And where do we even start?

Speaker 3I mean, a two-hour outage. Storefronts down, checkouts down, Admin down!

RachelAll at once PYMNTS had the timeline on it, and then, same week, they announce a three billion-dollar bump to their share buyback program.

Speaker 3Which brings total authorization to five billion. So, rough week operationally, bold move financially. We'll see what to make of that.

RachelAnd then we get into AI which I am genuinely pumped about. Amazon's got a new visual interface Dual image search tool. You describe something, it generates images, and you shop from those.

Speaker 3Kaarin Moore covered that, and Macy's is using AI to go after cart abandonment before it even happens,

RachelOf

Speaker 3which, honestly, I want to see the actual conversion data on.

Rachelcourse you do.

Speaker 3That's the whole question, right? Plus, Meta's WhatsApp Business Agent just went global. Big deal for conversational commerce.

RachelAnd we wrap with logistics and cross-border stuff. New fulfillment capacity in the Great Plains, Wayfair's margin plays, and why tax compliance is quietly killing cross-border growth for a lot of brands.

Speaker 3A lot of ground to cover. All right, let's get into it, starting with Prime Day.

RachelThree easy ways to get your questions to us. Check the description for our web form, text us at 747-293-4612, or call the same number to leave a voice question. However you reach out, we can't wait to hear from you. Alright, so if you sell on Amazon, I need you to stop whatever you're doing right now. June 9th—that's today, basically—that's the deadline to submit deals for Prime Day.

Speaker 3Yeah, and Prime Day itself kicks off June 23rd, so if you missed that window, I'm sorry. But if you're still in it, drop everything.

RachelIna Steiner reported this week that Amazon extended the deadline to get deals in, which is actually kind of them, but the clock is done.

Speaker 3Right, so the generous extension has expired. Great.

RachelSo here's the thing. Even if you can't submit a deal now, you should still be watching this Prime Day closely because this year looks different.

Speaker 3How so?

RachelGrocery. Amazon is going all in on grocery deals this year. Sarah Mahoneys covered this, and the framing is pretty clear. Shoppers are stressed about food and gas prices, and Amazon is meeting them there.

Speaker 3That's a real shift. I mean, historically, Prime Day was electronics, gadgets, the big ticket stuff. Grocery is, that's a different customer psychology entirely.

RachelTotally. And for brands and consumables, this is huge. You're not competing for attention in the same way you were two years ago.

Speaker 3And the margin picture gets complicated fast. Grocery is notoriously thin, so Amazon leaning into it tells you they're playing a longer game here.

RachelWhat game do you think that is?

Speaker 3Habit formation. Get people buying groceries on Prime, they're locked in. The subscription value goes way up. It's not about the margin on a box of cereal.

RachelRight. It's about the next 200 purchases, which honestly, as someone who's watched brands obsess over one-time conversion rates, this is the mindset shift most of them are missing.

Speaker 3And Amazon knows this better than anyone. They've been playing the long game since like 2005.

RachelYeah, they've had some practice.

Speaker 3So if you're a consumables brand and you're not set up for subscribe and save, or you haven't thought about how Prime Day fits into your replenishment strategy, now's the time.

RachelHard agree. Okay, so speaking of Amazon playing a long game, let's talk about South Africa.

Speaker 3Oh yeah, this one is wild.

RachelSo Amazon just launched Prime in South Africa, according to Bizcommunity, that was June 3rd, and the pricing is aggressive. if we're talking R59 rand a month.

Speaker 3Which is roughly $3.61 USD. Ayodeji Adegboyega over at Business Insider Africa covered this, and the framing was basically Amazon showing up to a fight.

RachelYeah, Takealot has been the dominant player there, and Amazon just walked in and said, here's Prime, here's the price, and oh, by the way, your first Prime Day is June 23rd to 29th.

Speaker 3Wait, so South Africa's first ever Prime Day is happening at Opening at the same time as everyone else's?

RachelYep; same window; and, deal submissions for South African brands, Bizcommunity had the deadline as June ninth; so, again, to day.

Speaker 3That is a fast ramp, like you just launched Prime three weeks ago and you're already running a major sale event?

RachelI know, right?

Speaker 3Wow!

RachelThat's not a soft launch, that's a statement.

Speaker 3From an operations standpoint, that's genuinely hard to pull off. I've seen companies spend months just getting the logistics aligned for a single

Speaker 4promotion.

Speaker 3For single market, Amazon is doing this at scale – internationally, simultaneously.

RachelAnd for brands watching this, the question is, are you even set up to sell cross-border? Because Amazon just opened a door in one of Africa's biggest e-commerce markets.

Speaker 3Right, and it's not just about listing your products. Tax compliance, currency, fulfillment – cross-border is messy. The brands who move fast here will have a real first mover window. window.

RachelThere's going to be a lot of we should have been there already conversations in boardrooms this week.

Speaker 3There always are.

RachelEvery single time.

Speaker 3But here's what I keep coming back to: Amazon Prime R59, that's clearly a land grab price. That's not sustainable at face value. So what does that tell you about their confidence in the market?

RachelThey're betting on volume and ecosystem lock in. Same playbook they ran in India, honestly.

Speaker 3Exactly. And Takealot has to be sweating right now.

MaxYou don't just compete with Amazon on price, you have to compete on the whole package, Prime Video, same-day delivery, all of it.

RachelYeah, good luck outbidding that.

MaxSo the net of all this, Prime Day June 23rd, grocery is the headline angle in the U.S., South Africa is the global headline, and if you're a seller, the deal deadline was today.

RachelAnd honestly, even if you're not a seller, pay attention to where Amazon is expanding, because it signals where the next wave of e-commerce infrastructure and Sure investment is going.

MaxTotally. And infrastructure investment has a way of creating its own set of winners and losers very quickly.

RachelSpeaking of infrastructure confidence, there's another platform that just made a pretty bold financial move this week and then almost immediately had to answer some uncomfortable questions about it.

MaxOh, you mean the company that simultaneously announced a massive buyback and then had its stores go dark?

RachelWhat does it say when a company bets big on itself the same week everything breaks? All right, shifting gears a little. So while Amazon's out here expanding into new continents, Shopify had, let's call it an eventful week.

MaxThat's one way to put it. Two rough things in the same week.

RachelYeah, so Wednesday morning, June 3rd, merchants woke up and basically nothing worked. PYMNTS reported the outage started at 9:27 a.m. EDT. Storefronts down, checkouts down, admin access down. retail POS down, even Shopify support was unreachable.

MaxUgh, so if you had a problem, you couldn't even ask for help.

RachelExactly. And Search Engine Land covered this too. It lasted about two hours. Shopify said at 10.37 they'd identified the issue, and by 11.31 it was resolved. Two hours.

MaxTwo hours sounds short on paper.

RachelRight? But if your entire business runs through Shopify, two hours on a Wednesday morning is not nothing. Like I keep thinking about the small merchant who's got a flash sale running. No Checkout, no store, just gone.

MaxAnd no way to communicate with customers either, since support was down. That's the part that gets me.

RachelHmm.

MaxIt's not just lost sales. It's customers who tried to buy something, couldn't, and maybe didn't come back.

RachelCart abandonment you can't even re-target because the transaction never started. That's painful.

MaxReally painful. And look, outages happen. Then every platform has them. But the timing question is real. We're days away from Prime Day, sellers are prepping, traffic is about to spike.

RachelAnd your platform goes down mid-week.

MaxNot great.

RachelNot great at all. So that's the rough part. But here's the wild part of the week.

MaxOh, there's more?

RachelThe same week the outage happened, Shopify announced a $3 billion increase to its share repurchase program. $3 billion. CityNews Halifax had the details: it brings their total repurchase authorization up to five billion, and as of June first they'd already bought back around one point four five billion under the current program.

MaxSo that's a company that thinks its stock is undervalued. That's what a buyback says.

RachelRight? And what's your read on that from an ROI standpoint?

MaxSo a buyback at this scale is a signal. You're telling the market, we have cash, we believe in ourselves, and we'd rather own more of our own stock than spend it somewhere else right now. At Amazon, I saw this play out with different capital allocation decisions. The question I always asked was, What are you not spending that money on?

RachelWhat do you mean?

MaxLike, you've got a platform that just went down for two hours, you've got merchants rattled, is five billion in buybacks the move, or do you put more into infrastructure resilience? I'm not saying it's the wrong call, I'm saying it's a choice.

RachelThat is such a Rachel question.

MaxI've been told.

RachelBut it's fair. And honestly, Kalkine Media had a piece this week asking whether Shopify can keep winning the digital commerce race. They flagged merchant activity, payments adoption, enterprise demand. The fundamentals look solid. But an outage right before the biggest shopping event of the summer is not the kind of story you want attached to those fundamentals.

MaxNo, and the competitive picture matters here.

RachelRight.

MaxYou've got WooCommerce, you've got BigCommerce, and Amazon itself building out tools for independent sellers. The merchants who stayed on Shopify through Wednesday did so because the switching cost... Switching cost is high, but every outage is a moment where someone starts doing the math.

RachelStarts Googling alternatives.

MaxExactly.

RachelSo does the buyback change anything for you? Like, does it offset the outage concern?

MaxNot directly. The buyback is a financial statement. The outage is an operational one. They're not canceling each other out. What I'd want to know is, what's Shopify's actual uptime record over the past 12 months? One two-hour incident or a pattern? Pattern.

RachelThat's the real question, yeah-one bad day versus a systemic problem.

MaxAnd right now we just have one data point.

RachelWhich, to be fair, Shopify resolved fast and communicated clearly. PYMNTS noted they were posting status updates throughout.

MaxTransparency matters. Merchants notice that.

RachelSo the week in summary: outage, buyback and a lot of merchants probably stress checking their backup plans.

MaxNothing like a good outage to make you audit your stack.

RachelRight. And speaking of how merchants are finding new ways to stay competitive with or without platform hiccups, there's a whole wave of AI tools reshaping how customers actually discover and buy products. Like Amazon just dropped something genuinely interesting on the search side.

MaxOh yeah, the image generator thing?

RachelYeah. And Macy's is using AI to close carts before people walk away. The numbers in that one are worth talking through.

MaxSeven in ten carts get abandoned. If AI is actually moving that needle...

RachelThat's where we're going. All right, shifting gears from platform drama to something a little more front end, the way shoppers find products is changing fast and sellers need to pay attention.

MaxYeah, and I think this is the part people underestimate. It's not just about SEO anymore.

RachelRight, so Amazon just launched an AI image generator inside its app. Kaarin Moore covered this. The idea is wild when you think about it. A shopper describes what they want, the AI generates a... It's a bunch of visual options, and then they shop from those images.

MaxWait, so they're not even typing a product name?

RachelExactly. Think about it like this. You know how on dating apps you don't search for tall, brown hair, likes hiking in a search bar? You just swipe through images until something clicks.

MaxI mean, I've heard of those apps.

RachelSure you have. But that's basically what Amazon is doing with product discovery. You skip the keyword step entirely. The AI bridges the gap between I'll know it when I see it and actually buying the thing.

MaxSo from a seller perspective, what does that mean for listing optimization? Because everything we know about keyword stuffing and search ranking.

RachelChanges, potentially a lot. Kimberly Shenk had a great...

Maxpiece in Fast Company. The argument is we don't naturally think in product terms; we think in pain points and goals. AI is finally catching up to that.

RachelAnd that's actually a huge shift in the funnel because right now, if your product isn't showing up in text search, you're invisible. But with visual discovery, the criteria change entirely.

MaxImages, visual branding, style match; that stuff matters more now.

RachelRight, which is uncomfortable for a lot of brands who've who've built their whole strategy around keyword rankings.

MaxTotally. So the sellers who figure out visual first are going to have a real edge. And here's the other piece: Macy's is already testing what AI can do with the other end of the funnel.

RachelThe cart abandonment angle.

MaxExactly. PYMNTS reported on this. Seven in ten online shopping carts are abandoned before purchase. Seven in ten, Rachel. Retailers have been chasing that number for dec

Speaker 4-

Maxfor decades.

RachelAnd nothing's moved the needle much, much. Discount pop-ups, retargeting emails, loyalty nudges, most of it is just noise at this point.

MaxSo Macy's built something called Ask Macy's. It's a conversational AI shopping assistant, runs on Google's Gemini, and the idea is to resolve the uncertainty before someone leaves, not chase them after.

RachelOkay, that's a smarter frame because by the time someone abandons, you've already lost the moment. moment. The question is what made them hesitate in the first place.

MaxSize questions, fit concerns, does this work with what I already have, that's what kills purchases.

RachelAnd a chatbot that can answer those in real time is basically a sales associate at scale, if the answers are good.

MaxThat's the key, if the answers are good, and that comes down to product data quality, which is its own whole mess.

RachelOh, I've seen that mess up close. If your catalog data is garbage, your AI just Just confidently gives wrong answers faster.

MaxConfidently wrong. Great combo.

RachelSo the ROI question for sellers is, what's your cost to fix the underlying data versus how much revenue are you leaving in abandoned carts? Usually it's not close.

MaxGood math to run. Okay, last piece here because it moves the needle fast. Ivan Mehta at TechCrunch covered this Wednesday. Meta's business agent for WhatsApp is now live globally.

RachelOkay, this is a big one for anyone selling outside the U.S. Alright!

MaxHuge! WhatsApp is already how a lot of the world shops and communicates. Meta spent nearly two years testing this in specific markets; now it's everywhere.

RachelAnd businesses pay based on token usage, so the cost scales with how much the AI actually works. That's a pretty clean model if your conversations are converting.

MaxFor small and mid-sized sellers, this opens a real conversational commerce channel without needing to build anything custom. The infrastructure is just... There!

RachelThat's the piece that matters. Lower barrier to entry for markets where WhatsApp is the default communication layer.

MaxAnd when you combine that with visual discovery on Amazon and AI closing carts on site, the whole customer journey is starting to look pretty different.

RachelFront-end discovery, mid-funnel conversion, global messaging. AI is threading through all of it now.

MaxBut here's the thing, none of that matters if you can't get the product to someone's door. And that's exactly where we're headed next: the back end of the story, logistics, fulfillment capacity, and why brands keep underestimating the operational side of growth.

RachelThe fun part: Nothing says glamorous e-commerce like warehouse square footage.

MaxShifting gears to the stuff nobody tweets about but everyone feels in their margins.

RachelThe operational grind?

MaxExactly.

RachelSo FreightWaves reported this week that Rush Order and Encore Fulfillment both opened new warehouses in the Great Plains. Rush Order's fourth U.S. center drops in Dallas-Fort Worth on July 1st.

MaxI mean Great Plains Logistics. Riveting headline, right?

RachelRiveting. But here's why it matters. Mid-market brands have been stuck choosing between coastal warehouses and slow ground shipping to the middle of the country. You put a node in Dallas and you shave one to two days off delivery times to like a third of the U.S. population.

MaxOkay, that's actually real. Speed is still the conversion lever nobody's done squeezing.

RachelRight. And Wayfair is doing the same thing from the inside. Supply Chain Dive covered their three logistics upgrades and it's a good case study. automated driver calls to customers, delivery consolidation, better last mile analytics.

MaxWait, automated driver calls?

RachelYeah, so instead of a driver calling to confirm a delivery window, it's handled automatically. Sounds small, but when you're doing millions of deliveries, that's real cost savings.

MaxAnd Wayfair is not exactly operating with fat margins right now, so.

RachelNo, which is kind of the point. Operational investment is how you protect margins when you can't just raise prices.

MaxOkay, so what about cross-border, because that's the other side of growth that feels like it should be easier than it is.

RachelSo Dulles Krishnan from Avalara wrote a piece for IBS Intelligence on exactly this. Global B2C e-commerce is projected to exceed $16 trillion by 2030. B2B, over $62 trillion.

Max$62 trillion?

RachelAnd the bottleneck isn't product. It's not even logistics. It's tax and compliance infrastructure. Every market has different VAT rules, import duties, filing requirements.

MaxSo brands expand, hit a compliance wall, and just stop?

RachelOr worse, they don't stop and they get fined. The Payoneer APAC interview over at TNGlobal made the same point. Nagesh Devata said the payment and compliance layer is becoming as important as the storefront itself in Asia-Pacific.

MaxWhich tracks? You can have the slickest checkout in the world and still lose money on cross-border orders if the tax setup's wrong.

RachelThat's the practical takeaway. Before you expand into a new market, the compliance infrastructure has to come first, not as an afterthought.

MaxBoring? Yes. Expensive to ignore? Absolutely. All right, that's a wrap on this one. What a week for e-commerce, honestly.

RachelYeah, so much packed in. The thing that keeps sticking with me is Rachel's framing on the Shopify buyback. $5 billion in repurchases while merchants are still shaken from a two-hour outage. That capital allocation question's real.

MaxRight, right. And on the Amazon side, the South Africa Prime launch at $59 random month? I mean, that's not a quiet test. That's a full commitment to a market. Get.

RachelAnd the grocery pivot in the U.S. ties into the same logic: habit formation at scale. That's the long game.

MaxBasically, the takeaway from this whole episode is Amazon is playing chess in like four countries at once, Shopify is figuring out what confidence actually costs, and AI is quietly rewriting how shoppers even find products.

RachelNot a bad week to cover.

MaxNot bad. Not at all. Okay, if you got value out of today, subscribe wherever you listen, and hey, a review goes a long way, seriously.

RachelIt really does. Thanks for spending time with us.

MaxWe'll see you next week. Take care, everyone.