Holiday Readiness in 2026: Two Experts Share What Marketers Need to Get Right

"The biggest mistake I see brands make is focusing only on promotions and forgetting everything required to support them. Inventory, fulfillment, website performance, delivery expectations, supplier alignment, customer service readiness, and clear messaging all need to work together. Holiday success is more than one great campaign; it's about making sure every operational piece is ready for the surge in demand. If customers encounter stock issues, confusing delivery promises, or fulfillment delays, marketing becomes irrelevant. The best brands simplify the experience for customers while reducing complexity behind the scenes. That's how they avoid the problems that typically create service issues during peak periods."

"The biggest priority this year is flexibility. Retailers need plans for both stronger-than-expected demand and weaker-than-expected demand. Consumer behavior remains difficult to predict. Brands should know which products they plan to promote, what happens if inventory sells out, what substitute products are available, how messaging changes if demand slows, and when to adjust pricing or media spend. Agility is what separates successful retailers from struggling ones. Holiday planning is all about preparing multiple paths forward and being ready to react quickly when consumer behavior shifts."

"Most retailers are seeing more and more customers using tools like ChatGPT, Claude, Gemini, and similar platforms during the research phase. So, brands need to think about how they appear inside those environments because that's increasingly where discovery begins. If companies haven't started investing in answer engine optimization, generative search visibility, or content that can be surfaced by large language models, they're already behind. On the business side, AI will help marketers plan faster, identify opportunities, automate reporting, and operate more efficiently."

"AI's greatest impact will be on customer experience. Consumers are increasingly using conversational tools to research products, compare options, and find gift ideas. At the same time, retailers are embedding AI into search, product discovery, customer service, and support experiences. During holiday periods, customer service inquiries spike. AI agents can help manage that volume, answer routine questions, and provide shoppers with immediate information about delivery, returns, and product availability. They can also help marketers react faster to changes in performance, identify issues, and recommend actions in real time."

"The holiday season isn't the time to experiment with major changes. It's the most important quarter of the year for many retailers. What marketers should focus on is using automation to remove low-value work after peak season so their teams can spend more time on strategy, creativity, and growth. The real opportunity is creating space for people to contribute where human thinking matters most. AI should eliminate repetitive tasks and operational friction. If it does that well, marketers can spend more time creating value, exploring new markets, improving customer experiences, and developing better ideas."

"Humans still want to remain involved in important decisions. Most marketers are comfortable using AI for recommendations, analysis, and alerts. Fewer are comfortable fully automating high-stakes decisions during a critical sales period. That's understandable. Holiday performance carries significant accountability. The smartest approach is defining what AI is allowed to do, what requires human approval, and where teams are comfortable automating actions. Automation should increase speed and confidence, not eliminate oversight."

"Many holiday problems are predictable. Delivery delays, inventory shortages, pricing confusion, and service bottlenecks happen because brands didn't plan far enough ahead. Every touchpoint needs to be considered before peak traffic arrives. Customers shouldn't have to guess when orders will arrive or what happens if circumstances change. The simpler you make things for customers, the fewer issues you create for your teams. Holiday periods expose operational weaknesses very quickly, so preparation matters more than last-minute execution."

"One of the most common mistakes is underestimating the importance of delivery communication. Customers don't stop caring once they've purchased. In many ways, that's when anxiety peaks. They want updates, confirmation, transparency, and confidence. Brands should think carefully about how delivery communications can become part of the customer experience. Another mistake is focusing only on the transaction. The most successful retailers think about the next action they want customers to take after the purchase."

"Holiday is often the largest customer acquisition period of the year. That means retailers need a plan for what happens next. Acquiring a customer is only the first step. If brands don't actively work to generate repeat purchases, they've missed one of the biggest opportunities available to them. The goal should be to build relationships that continue long after peak season ends."

"Retailers spend enormous amounts of money acquiring customers during the holidays. The brands that win long-term think beyond that first conversion. What behavior led customers to become loyal in previous years? Can it be replicated? Can it be systematized? Should shoppers join the loyalty program, make a second purchase, subscribe, or engage with another product category? Every acquisition strategy should include a retention strategy. Otherwise, marketers are forced to start from zero again next season."