The Checkout Is Moving Into the Chat
Plus: Zendesk says 88% of customers expect faster response times than last year
📅 January 9, 2026 | ⏱️ 4-min read
Good Morning!
The Executive Hook:
You know what’s quietly happening? The “front door” to your brand is moving. Not to a new app. Not to a new website. To a conversation. Customers are starting with an AI assistant, getting advice there, and now—depending on the company—buying there too. That’s a big shift for CX, because your best-designed journey doesn’t matter much if the customer never enters it.
🔍 THE DEEP DIVE: Microsoft turns Copilot into a checkout lane
The Big Picture: Microsoft is adding in-chat checkout to Copilot, so customers can go from “what should I buy?” to “done” without leaving the chat.
What’s happening:
Copilot can recommend products and show “Details” and “Buy” buttons right in the conversation.
When someone clicks “Buy,” checkout happens inside Copilot—not on a retailer’s site.
Microsoft says it’s rolling out on Copilot.com in the U.S. with select retail partners, with payments handled through providers like PayPal, Stripe, and Shopify.
Why it matters:
This is the part CX leaders should stare at: the experience you designed may not be where the customer decides. If the “storefront” becomes the AI assistant, your brand wins (or loses) based on what the assistant can confidently explain in the moment—price, availability, shipping promises, returns, and what makes you different.
And here’s the uncomfortable truth: if your policies and product info are messy, inconsistent, or buried in PDFs, the AI experience will feel messy too. Customers won’t blame “the bot.” They’ll blame you.
The takeaway:
Start treating “AI shopping conversations” like a real channel. That means tightening the basics: clean product data, current inventory, plain-English policies, and fewer surprises after purchase. In a chat checkout world, clarity is conversion.
Source: The Verge
📊 CX BY THE NUMBERS: Speed expectations just leveled up
Data Source: Zendesk — CX Trends 2026: AI & Contextual Intelligence
88% of customers expect faster response times than they did a year ago. (Translation: last year’s “good” is this year’s “slow.”) (Zendesk CX Trends 2026)
74% of consumers expect customer service to be available 24/7. (Customers don’t care what time your team clocked out.) (Zendesk CX Trends 2026)
The Insight:
Customers aren’t becoming “impatient.” They’re being trained—by the fastest experiences they have everywhere else. So the bar for “responsive service” keeps moving up. If you can’t meet it with humans alone (most teams can’t), AI isn’t optional… but it has to be implemented in a way that protects trust, not just reduces handle time.
🧰 THE AI TOOLBOX: Talkdesk Commerce Orchestration
The Tool: Talkdesk announced Commerce Orchestration powered by its Customer Experience Automation (CXA), aimed at supporting conversational commerce across the shopper journey.
What it does: Brings AI-driven workflows together across discovery, sales, and service—so customers can get help, make changes, and complete tasks without bouncing between systems.
CX Use Case:
When a customer asks, “Where’s my order?” the experience shouldn’t be a scavenger hunt. This kind of orchestration is built to pull steps together—status, changes, escalations—without ten handoffs.
For retail and consumer brands, it’s a direct play at reducing friction in the moments that create the most anger: delivery issues, returns, substitutions, and “I need this changed right now.”
Trust:
Orchestration is where “AI” stops being a chat window and starts being a promise: we can actually solve the problem. If your automation can’t complete the task (or makes the customer repeat themselves), it’s not efficiency—it’s frustration at scale.
Source: GlobeNewswire
Case Study: Rocky Brands
⚡ SPEED ROUND: Quick Hits
Google brings more Gemini features into Gmail (including AI overviews and writing help). CX angle: the “agent assist” pattern is moving into everyday workflows—people will expect the same kind of help from your service experiences too. (blog.google)
Workday adds AI innovations aimed at frontline retail and hospitality teams. If it actually helps with scheduling and day-to-day chaos, customers feel it as shorter lines, fewer “we’re slammed,” and less of that deer-in-headlights moment when someone can’t find an answer. (Workday Investor Relations)
SAP announces more AI-infused retail capabilities at NRF 2026. The interesting part isn’t the features—it’s the direction: brands want fewer disconnected systems so the customer doesn’t get punished for the company’s internal mess. (SAP News Center)
📡 THE SIGNAL: Chat makes “slow” feel even slower
When checkout and service move into a conversation (like Copilot is doing), customers assume the chat is the whole experience—not the front porch. So the moment they ask, “Can I buy this?” or “Where’s my order?” they expect it to be handled right there.
That’s why Zendesk’s “88% want faster responses” matters. The patience budget is shrinking. And once you put the experience in a chat window, any gap—waiting, bouncing to a site, repeating details, getting routed around—feels twice as frustrating.
This is also why orchestration is the real story underneath the shiny AI layer. If the assistant can’t actually complete the purchase, change the delivery, process the return, or pull the right account context, then all you’ve built is a faster way to disappoint people.
See you Monday!
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