Instacart Beats Walmart and Target to ChatGPT Checkout 🚀

Maybe this is Instacart’s way of telling Walmart, Target, and Etsy: talk less, ship more 🚢.

Hi there, and welcome to another issue of The Ecom Press 🗞️!

Instacart takes the Instant Checkout crown with the first live ChatGPT integration. Pinterest turns Recipe Pins into real carts with Walmart. And Visa teams up with AWS to build serious infrastructure for agent-led shopping 🤖.

Also, we’ve got a sharp case study on using AI to spot churn and bring customers back.

Let’s dive in shall we 😉?

In a rush? Here's the juice🤭:

🚀 Instacart beats Walmart and Target to ChatGPT checkout.

🛒 Pinterest x Walmart partner for instant grocery shopping.

🤖 Visa launches agentic commerce stack on AWS.

🔍 Case study: How one brand predicted churn and won back customers with AI

⚡️Worthy Mentions

🚀 Instacart beats Walmart and Target to ChatGPT checkout.

Instacart has become the first company to offer Instant Checkout directly inside ChatGPT, allowing users to shop and pay for groceries without leaving the conversation. The new integration is powered by OpenAI’s Agentic Commerce Protocol and aims to streamline everything from meal planning to cart delivery in a few clicks.

Here’s the lowdown ⬇️:

🛒 From chat to cart to checkout: Ask ChatGPT to help with a grocery task, like finding ingredients for apple pie, and the Instacart app auto-launches inside the chat. Once signed in, users get curated cart suggestions, and can check out directly inside ChatGPT via Stripe-powered Instant Checkout.

📦 Real-time grocery tech under the hood: Instacart leverages 2B+ product listings across 1,800 retailers and nearly 100,000 stores. The app uses up-to-date inventory and local pricing to surface what's actually in stock.

📱 Live now on web, mobile coming soon: The experience is available on desktop and mobile web. iOS and Android app rollouts are expected in the coming weeks, with Apple Pay and Google Pay support soon to follow.

🤖 OpenAI’s agentic commerce push: This move expands ChatGPT’s utility beyond conversation. OpenAI will take a small cut per transaction, laying the groundwork for monetized shopping agents at scale.

Why it matters 🤷‍♂️

While companies like Walmart and Target announced plans to integrate ChatGPT shopping features back in October, the key difference here is execution. Instacart is the first to have a fully live, end-to-end shopping experience, including Instant Checkout, operating inside the ChatGPT interface.

Ecommerce is moving toward embedded, AI-driven experiences, not just faster sites or smarter ads. For merchants, it’s a signal to rethink how discoverability and conversion might work when the storefront is a chatbot. 

🛒 Pinterest x Walmart partner for instant grocery shopping.

Pinterest and Walmart are teaming up to make grocery shopping more seamless. Through a new shoppable recipe experience, Pinterest users in the U.S. can now add ingredients from recipe Pins directly into their Walmart cart with a single tap, blending inspiration and execution in one fluid flow.

Here are the deets ⬇️: 

🥕 “Shop Ingredients” goes live: Eligible recipe Pins now feature a “Shop Ingredients” button that sends selected items straight to Walmart’s site or app. Users can swap products, view real-time pricing, and choose between pickup or delivery from their preferred store.

📈 Capitalizing on grocery’s online growth: With 61% of U.S. households buying groceries online and July sales up 26% YoY, the timing is ideal. Pinterest says the feature delivers on expectations for frictionless shopping.

📌 Pinterest doubles down on commerce: Now at 600M monthly active users, Pinterest has made commerce a core growth lever. Recent initiatives include:

• 1,000+ holiday gift guides with direct checkout links

• A beauty analysis tool with E.l.f. Cosmetics

• “Where-to-buy” ads for CPG brands

Why it matters 🤔

This shows how platforms are moving closer to daily utility. It’s not just about ads or clicks but about solving real-life tasks like grocery planning in fewer steps. The more you reduce friction between discovery and purchase, the more likely customers are to follow through.

🤑 Sponsored tip of the week

🛒 Sell Everywhere from One Place with Shopify Sales Channels.

From Instagram and Facebook to your blog, the Shop App, or even in-person — Shopify lets you manage all your sales channels in one dashboard.

Easily sync your product catalog, track orders, and engage customers across platforms like POS, Shopify Inbox, and your online store — no need to juggle tools or tabs.

👉 Sign up with Shopify for just $1.

🤖 Visa launches agentic commerce stack on AWS.

Visa and Amazon Web Services (AWS) have joined forces to power agentic commerce. Their new collaboration gives developers everything they need to build secure, autonomous buying systems, from payment infrastructure to plug-and-play blueprints.

Here’s the scoop 🍨:

💳 Visa’s Intelligent Commerce goes cloud-native: Now listed on the AWS Marketplace, Visa’s Intelligent Commerce provides tools for tokenization, authentication, personalization, and secure payment execution, all tailored for AI agents managing purchases end-to-end.

🧱 Blueprints for rapid deployment: Developers can now access prebuilt agentic commerce workflows in the Amazon Bedrock AgentCore repo. These include templates for shopping, booking, payments, and post-purchase reconciliation.

🔐 Trust layer for autonomous transactions: Visa is positioning its platform as the security backbone of agent-driven commerce. Combined with AWS’s cloud reach, the goal is to help agents transact securely and at scale.

🌐 Built for multi-network ecosystems: While Visa leads the payment infrastructure, the tools are built to support network-agnostic commerce, not just Visa transactions.

🤝 Big names already onboard: Partners like Expedia, Intuit, and Eurostars are already exploring use cases tied to agentic travel and shopping workflows.

Why it matters 🤨

As agentic commerce grows, it’s not just apps and interfaces that need to evolve but the infrastructure behind them must scale too. This partnership contributes to the groundwork for AI agents to communicate, transact, and fulfill reliably across multiple brands. The stronger that backend becomes, the more seamless, and widespread, agent-to-agent commerce will get in the years ahead.

🛎️ The Ecom Press Insider

Ecom Fact: 84% of U.S. consumers say holiday promotions are confusing, unclear, or misleading. Nearly half (45%) say they’ll stop shopping with retailers they no longer trust, especially if promo execution feels off.

That’s according to Relex Solutions, which attributes the disconnect to poor alignment between marketing, pricing, and supply chain systems. When messaging doesn’t match inventory or pricing logic, it destroys customer confidence fast. Before your next promo goes live, make sure your pricing, inventory, and comms are speaking the same language.

🔍 Case study: How one brand predicted churn and won back customers with AI

A mid-sized ecommerce brand had a retention problem. Many customers weren’t coming back, and they had no system to flag who was likely to churn.

🚧 The Challenge: Instead of blanket marketing, the goal was to shift toward behavior-based retention. But the team lacked the tools to segment their customer base or intervene early.

🛠️ The Solution: The brand connected its Shopify sales data to a lightweight analytics workflow. Every night, it ran a customer segmentation using RFM analysis, grouping customers by how recently and frequently they shopped, and how much they spent.

When a customer shifted into the “at-risk” category (say, 90 days without an order when their usual pattern was 30 days), the system automatically triggered a targeted email. Each email offered a personalized, welcome-back deal designed to win them over.

🧾 The Results:

• 15% drop in churn within six months 📉

• 10% lift in customer lifetime value 💰

• Higher campaign profitability thanks to sharper targeting 🎯

💡 Takeaway

Retention doesn’t always need a big-budget CRM overhaul. Simple behavior triggers can do the heavy lifting, especially when paired with targeted offers and solid segmentation. If you're still guessing who’s slipping away, it might be time to automate your comeback plan.

⚡️Worthy Mentions

• Amazon slashes seller fees in Europe to counter Temu and Shein.

• TikTok Shop smashes $500 million during Black Friday Cyber Monday.

• Skims enters live entertainment with interactive TikTok shopping stream.

• OpenAI hits 'code red' over Google's Gemini 3, pauses ChatGPT ads.

• Ashley partners with Perplexity for AI-driven furniture purchases.

Wrapping up…

Beyond sales, the holiday season seems to have become a launchpad for the future of shopping, with different releases and partnerships 🤝.

But what stands out now? Speed, trust, and how well you connect the dots across the entire customer journey 🏄.

Catch you next week, and if you haven’t subscribed yet, now’s a great time to fix that 😉.