Retail is sprinting into 2026, and the finish line keeps moving. We sit down with Deanah Baker and Scott Benedict to chart where the next big shifts will land: AI that actually clears friction, merchants who think across channels, and retailers racing to align speed, execution, and value. If you’ve felt the workload double since omnichannel merged teams, you’ll hear why the answer isn’t more hours, it’s smarter tools, cleaner data, and leaders who model new ways of working.
We dig into Amazon’s bold supercenter test in Orland Park and what it signals after years of smaller bets. Is this the long-awaited counterpunch to Walmart’s supercenter dominance? On the specialty side, mid-tier apparel faces a tough truth: financial strain delays tech adoption, even as RFID, sharper attribution, and faster cycles become survival gear. Target, once the gold standard for store discipline, needs to rebuild basics, on-shelf availability and execution, before the brand can shine again. Kroger’s at a crossroads with strong private brands but dented price trust and uneven service investments, while regionals press the pace.
Then there’s Aldi, expanding aggressively by doubling down on its limited-SKU, private-brand engine. The model travels, but only if logistics and inventory turns stay razor-sharp, because out-of-stocks in a narrow assortment break trips fast. Meanwhile, club formats; Costco, Sam’s Club, and BJ’s, prove that curated value and omnichannel convenience can grow together. Private labels, upgraded specs, and low-friction tech keep engagement high.
Walmart’s AI partnerships (including Gemini) point to a practical strategy: learn broadly, act quickly, and keep customer search and discovery seamless. The goal isn’t just smarter results, it’s shortening the path from insight to shelf, syncing merchants, suppliers, and supply chains. The real moat is culture: curiosity, art-meets-science judgment, and global awareness that great ideas can start anywhere.
If you lead in retail or sell into it, this conversation will sharpen your playbook for the next 24 months. Subscribe, share with your team, and leave a review with your biggest takeaway, what shift are you betting on?
More About this Episode
Retail Trends 2026: AI, Omnichannel Merchandising, and the Future of Walmart, Amazon, and Beyond
Retail is not easing into the future. It is sprinting toward it.
As we look ahead to 2026, the pace of transformation across the retail industry is accelerating. Artificial intelligence, omnichannel integration, private brands, supply chain volatility, and shifting consumer expectations are reshaping how retailers operate at every level. From the merchant’s desk to the store shelf to the customer’s smartphone, retail is being rebuilt in real time.
In this second part of our retail trends discussion, we go deeper into what these changes mean for merchants, employees, and the major retailers shaping the industry, including Walmart, Amazon, Target, Kroger, Aldi, Costco, and Sam’s Club.
The future of retail is not theoretical. It is operational. And it is happening now.
The Rise of the Holistic Merchant
One of the most significant shifts in retail leadership heading into 2026 is the emergence of what can be called the holistic merchant.
Historically, retailers operated in channel silos. Brick and mortar teams focused on physical stores. Ecommerce teams focused on digital. Each had its own metrics, processes, and mindset.
That model is disappearing.
Today’s retail environment requires merchants who understand both physical retail and ecommerce simultaneously. The customer no longer thinks in channels. They move seamlessly between online search, mobile browsing, curbside pickup, and in-store purchasing. Retail organizations must do the same.
The modern merchant must analyze data from:
- In-store sales performance
- Online search behavior
- Ratings and reviews
- Digital traffic trends
- Inventory flow
- Supply chain disruptions
- Retail media performance
This requires a new skill set. It requires retraining. It requires leadership that models digital fluency and encourages teams to embrace AI-powered tools that reduce repetitive work and free up time for strategic thinking.
Retail jobs are not disappearing. They are evolving.
The merchants who succeed in 2026 will be those who can balance art and science. They will use AI to handle data-heavy processes while focusing their energy on customer advocacy, assortment strategy, and trend anticipation.
AI in Retail: From Buzzword to Backbone
Artificial intelligence is no longer experimental in retail. It is becoming foundational.
While much public attention focuses on customer-facing AI, the most transformative applications may be behind the scenes.
AI tools are now being used to:
- Automate forecasting and demand planning
- Improve inventory accuracy
- Reduce repetitive data gathering
- Accelerate product development timelines
- Enhance search attribution and product discoverability
For example, Walmart’s continued investment in AI partnerships, including integrations with generative AI platforms, signals a serious commitment to using machine learning to improve both operations and customer experience.
AI-driven search enhancements will reduce friction in product discovery. That means customers will find what they are looking for faster. But it also means merchants must be better at product attribution, keyword optimization, and data accuracy to ensure products surface correctly.
Retailers that combine AI adoption with speed to market will win. Retailers that hesitate risk falling behind rapidly.
Amazon’s Supercenter Move: A Direct Challenge
Amazon’s announcement of a larger-format physical retail store signals a new chapter in its brick-and-mortar strategy.
After experimenting with multiple physical concepts over the years, Amazon’s strength in physical retail remains Whole Foods. But this new supercenter-style store appears to be a direct challenge to the dominance of the traditional big box supercenter model.
Amazon has already strengthened its grocery delivery and fresh food logistics. Expanding into a larger physical format suggests a desire to compete more aggressively in full-line retail.
If successful, this move could redefine how digital-first retailers enter physical retail at scale. If unsuccessful, it reinforces how complex and difficult physical retail execution truly is.
Either way, the test will be worth watching.
Specialty Retail: Survival Through Discipline
Specialty retailers face a more complicated landscape.
Mid-tier department stores and apparel retailers have struggled with:
- Inventory discipline
- Store execution
- Overexpansion
- Financial instability
- Slow technology adoption
Retailers like Kohl’s and JCPenney are working through turnaround strategies. Gap is attempting a resurgence across its portfolio of brands. Some luxury players are navigating financial distress.
The common thread is discipline.
Retailers that once excelled at store execution must return to operational basics:
- Full shelves at season launch
- Clean store presentation
- Clear value messaging
- Consistent merchandising standards
Customers still want differentiated shopping experiences. They want aesthetic variety. They want a choice beyond Amazon and Walmart.
But customers will not tolerate inconsistent execution.
Specialty retail is fixable. It simply requires leadership focus, financial stability, and renewed commitment to fundamentals.
Target’s Execution Challenge
Target remains a beloved brand in many ways. The emotional connection consumers have with the Target shopping experience is real.
However, recent challenges around inventory levels, in-store presentation, and operational consistency have impacted performance.
Target’s opportunity is not reinvention. It is re-discipline.
Customers want Target to succeed. The brand still holds equity. But precision execution, which once defined the company, must return to the forefront.
In retail, execution is strategy.
Kroger: At a Strategic Crossroads
Kroger enters 2026 in a moment of recalibration.
Following a high-profile attempted merger that did not materialize, the company must now double down on its standalone strategy. Private brands remain a strength. Retail media capabilities are developing. Grocery fundamentals are solid.
However, Kroger faces competitive pressure from:
- Regional grocery leaders like H-E-B and Publix
- Discount players like Aldi
- Club formats
- Omnichannel acceleration from national competitors
The path forward requires clarity in pricing strategy, continued private label innovation, and stronger omnichannel execution.
Kroger has the scale and assets to succeed. The question is speed and focus.
Aldi: Efficiency and Value at Scale
Aldi continues to expand aggressively, opening a significant number of stores annually.
Its model is disciplined:
- Limited SKU assortment
- Heavy private brand mix
- Lean labor structure
- Operational efficiency
In a value-focused environment, Aldi’s proposition resonates strongly.
However, rapid growth introduces logistical challenges. Limited assortment means out-of-stocks are particularly damaging. Inventory flow must be extremely efficient.
If Aldi manages supply chain execution at scale, its expansion could further disrupt traditional grocery competitors.
Club Retail: Costco, Sam’s Club, and BJ’s
The wholesale club format has proven resilient and adaptable.
Key strengths include:
- Membership loyalty
- High private brand penetration
- Efficiency-focused operations
- Increasing omnichannel integration
Kirkland Signature remains one of the most powerful private brands in the industry. Sam’s Club has leaned aggressively into technology integration. BJ’s has strengthened its grocery emphasis.
Club retail blends value perception with quality. That balance continues to attract consumers across income levels.
Walmart’s AI-Focused Future
Walmart’s continued investment in AI leadership, strategic partnerships, and digital transformation reinforces its commitment to staying at the forefront of retail innovation.
Rather than relying on a single technology partner, Walmart appears willing to experiment across multiple AI ecosystems to accelerate learning and capability development.
This approach reflects a core retail principle: serve the customer first.
AI in Walmart’s ecosystem will impact:
- Search functionality
- Personalization
- Supply chain forecasting
- Assortment planning
- Product attribution
The combination of scale, speed, and technology adoption positions Walmart to remain highly competitive heading into 2026.
The Retail Industry in 2026: Art Meets Science
Retail has always been both art and science.
The science side is becoming more powerful through AI, machine learning, data analytics, and automation. The art side remains critical through storytelling, brand curation, assortment decisions, and customer empathy.
The retailers that thrive in 2026 will:
- Invest aggressively in AI tools
- Maintain operational discipline
- Embrace omnichannel thinking
- Strengthen private brand strategies
- Preserve customer trust through transparent pricing
- Balance technology with human insight
Speed is no longer optional. It is essential.
At the same time, curiosity remains the foundation. Retail leaders must remain students of the consumer, students of global innovation, and students of emerging best practices beyond U.S. borders.
We are at an inflection point in retail history.
Those who adapt will build stronger, smarter, more resilient retail organizations. Those who hesitate risk being left behind in a marketplace that no longer waits.
The journey in 2026 is underway. The question for every retailer, merchant, and supplier is simple:
Are you running with it, or chasing it?
