Good morning and Happy New Year—Blake Bumgardner here, Head of Sales at Homesome.

We’re emerging from the holiday rush, that brief, intense window where every friction point in a retailer’s operation is magnified. Every week I get a front-row seat to how digital grocery is changing, but as we settle into 2026, the pattern has been impossible to ignore: the gap between the industry’s leaders and everyone else is widening—fast.

You can see it in a dozen places. In the rise of AI-powered shopping experiences. In how loyalty is quietly becoming the new retail media engine. In how national retailers are stitching together commerce, fulfillment, and data with the kind of speed that would’ve felt unrealistic even two years ago.

Amazon’s Rufus is pushing basket conversion up by nearly 60%. Walmart’s Sparky is turning a search bar into a full-time shopping companion. Albertsons has embedded conversational commerce into the core of every banner app. Those are important signals, but they’re not the whole story.

The deeper shift is this:

This edition is about that widening delta: why it’s happening, what it means for the next era of digital grocery, and how grocers of all sizes can compete when the terrain itself is changing underneath us.

Make sure to stick around for the Featured Insights after the main story for some of our favorite content from the past month!

🤖 Rufus, Sparky, Ask AI — Seven Imperatives for Retailers in the AI Era
💬 Featured Insight: Gary Hawkins, Retail Mindsteps
💬 Featured Insight: Matt Van Gilder, NexChapter

For most of the last decade, online grocery has been a sequence of tiny tasks: open the app, type burger meat, add to cart—then buns, condiments, chips, drinks. Five, ten, sometimes fifteen individual searches just to get a simple backyard barbecue off the ground.

And inevitably, something gets missed: paper plates, grilling tools, propane, the side everyone likes but nobody remembers.

That world is ending.

The front door of e-commerce has shifted from searching for items to stating intent.

Now the shopper starts with one question:
“I’m hosting a barbecue for eight, what do I need?”

Across the industry, companies like Amazon with Rufus, Walmart with Sparky, and Albertsons with Ask AI are signaling the same direction: a future where natural language replaces keyword hunting, where a single query can shape a full basket, and where the retailer who controls that interaction controls the path to purchase.

These systems aren’t just answering questions. They’re capturing intent—and whoever captures the intent owns the basket, the loyalty activation, and the downstream data that shapes the next trip.

For years, grocers have been wiring up the “invisible station” behind the digital shelf—a stack built piece by piece, often without realizing what it would one day enable:

Individually, each system solved its own narrow problem.

Together, they laid the groundwork for something more: a world where the shopper doesn’t navigate categories—they simply state intent.

Today’s AI assistants are beginning to weave that entire stack into a single, conversational flow:

Under the hood, none of this is magic. It’s the unglamorous backbone: clean taxonomies, reliable store feeds, price and promo APIs, and the disciplined data hygiene that makes every answer coherent rather than chaotic.

Chat is the glossy interface.

The hard part—and the advantage—lives in everything beneath it.

The front door for e-commerce is moving—and if retailers don’t move with it, every attempt to grow or retain a digital customer base becomes an exercise in throwing rocks at the sun. Here’s what success looks like in practice:

001 // Don’t let marketplaces own your AI experience.

Marketplaces aren’t going anywhere, nor should they. They’re lucrative, they drive volume, and for many retailers they’re an essential revenue line.

But here’s the risk: if a shopper’s first interaction happens inside a marketplace’s AI assistant, then the marketplace owns the intent, the logic, and the relationship. And once a customer gets comfortable asking a marketplace model what to buy, it becomes harder and harder to pull them back into your world.

Omnichannel shoppers are your most loyal, highest-value customers.
Don’t let the only AI they ever meet belong to someone else.
Marketplaces will always optimize for their network. Your AI should optimize for you.

002 // Make loyalty your life support system.

Personalization is where AI earns its keep.
Studies suggest chat-based personalization can lift conversion by up to 25%, and AI-powered shopping assistance can deliver multiples over search-only surfaces. But none of that works unless loyalty signals—purchase history, dietary needs, preferred brands, shopping patterns—flow directly into the conversation.

If your assistant can’t use loyalty to shape the cart, you’re just recreating Google with prettier colors.

003 // Make your content and data as ready as your interface.

AI can only answer with what you give it. Recipes, circulars, promos, attributes, substitutions—if the inputs are messy, the outputs will be wrong.

Winning here isn’t about having the flashiest bot.
It’s about having the cleanest foundation.

004 // Generate data at industrial scale.

Every shopper question is a focus group you didn’t pay for.
Treat chat logs as a new class of first-party insight:

This is the research budget you already have—you just haven’t opened the notebook yet.

005 // Graduate from keyword search to intent understanding.

Walmart’s GenAI search shows where the bar is headed: shoppers can ask for help planning a party, stocking a kitchen, or preparing for a newborn, and receive mission-based results.

The message is clear: AI doesn’t win by matching nouns. It wins by understanding why the shopper is here at all. If your assistant can’t decode intent, your competitors’ will.

Intent is the new entry point.

006 // Use what’s already there.

The best AI experiences don’t force customers to learn a new destination—they sit inside the places shoppers already are. Albertsons’ Ask AI works because it lives inside the existing app and search function.

Most grocers already have a goldmine of structured content: recipes, circulars, vendor media, in-store events, prepared meal guides. Feed it into your assistant so it answers with your voice and your knowledge—not whatever the open web decides is “close enough.”

AI doesn’t need a new world. It needs better inputs.

007 // Let AI enhance every surface—not just chat.

Chat is the front door, not the whole house.
The next advantage comes from weaving AI across:

• search
• PDPs
• shopping lists
• weekly ads
• recommendations
• substitutions
• full shopping journey

This is the shift: from isolated upgrades to a fully integrated intelligence loop that gets stronger with every shopper, every question, every trip.

by Gary Hawkins, CEO at Retail Mindsteps

A Good Idea at the Time.

The Request for Proposal (RFP) process did not emerge because retail was innovative—it emerged because retail was risk-averse, margin-tight, operationally complex, and needed a formal mechanism to control vendor selection. Over time, this mechanism has hardened into orthodoxy.

Retailers have long bought large volumes of commoditized goods—things like signage, fixtures, scales, shopping carts, and shelving. Procurement logic dominated: Standardized specifications were developed, vendors became interchangeable, and lowest price wins. The RFP structure borrowed from government contracting and industrial sourcing—process disciplines built for predictability, scale, and price competition. It worked because technology complexity was low and innovation cycles were slow.

As retailers began installing POS, scanning, early warehouse systems, and loyalty databases, the stakes increased. Mistakes became increasingly expensive. As a result, IT departments adopted the RFP process to manage vendors, mitigate integration risk, and budget accountability. The complexity of software made leaders default to formalized, documentation-heavy sourcing as a safeguard.

Sarbanes-Oxley brought with it the need for greater compliance; retailers became more bureaucratic. Procurement gained power, legal tightened oversight, and audit teams scrutinized vendor selection. RFPs offered protection against accusations of favoritism or mismanagement. Retailers weren’t optimizing innovation—they were optimizing defensibility.

As supply chains globalized and tech vendors multiplied, retailers saw an explosion of options in eCommerce platforms, loyalty systems, digital marketing, ERP, CRM, store automation, and cloud services. RFPs became a way to filter a crowded market, manage cross-functional alignment, and force structure onto an increasingly complex world.

As the industry started its digital transformation, retailers began to discover the limits of the RFP process. Tech solutions became increasingly complex, forcing more orchestration across the enterprise. Innovation began to rule; New tech no longer iterative, but data-driven, with a focus on new emerging capabilities. Meanwhile, the RFP model remained static, rigid, and slow.

Read the full article →

by Matt Van Gilder, Principal & VP of Omnichannel at NexChapter

This past fall conference season, I started to write down all the different titles I was seeing in the digital retail space. Head of Digital Commerce, Director of Connected Commerce, VP of Omnichannel, Manager of Unified Commerce. And of course, the classic: Director of eCommerce.

The terms get used interchangeably as if they are the same thing, but are they? I decided to take a deeper look and see whether I could figure out if we are just looking at synonyms or if there are practical and useful differences across these terms. I started by defining a few of the top terms I had seen: Omnichannel, Unified, and Connected. And through this process I uncovered just how some of this stuff fits together.

Omnichannel commerce at its core is about giving shoppers a consistent, low‑friction experience across every touchpoint. One customer. One profile. Many paths. Consistent experience.

Omnichannel commerce is not one thing. It is the combination of a unified foundation and a connected ecosystem.

Most retailers today believe they are moving toward omnichannel, but in reality most are operating in a multichannel state. Channels coexist, but they do not behave like one business. Prices drift, loyalty earns differently depending on the surface, data updates in one place but not the other. Customers never think in channels. They think, 'I shop you.' That gap is where friction lives. Naming unified and connected commerce is not a vocabulary exercise. It is a way to see where clarity cracked, and how to rebuild it intentionally.

Think about buy online pickup in store. Loyalty that works in the app, online, and at the register. Digital coupons that apply anywhere. Those are table stakes for omnichannel commerce and should be consistent and dependable.

And omnichannel commerce is not a checklist, it is a mindset. For the customer, omnichannel commerce is a seamless experience. For the retailer, it is a way of running the business. Every business function needs to approach their strategy and execution through the lens of the omnichannel. We meet the customer where they are and let them move between channels without losing context.

Read the full article →