The holiday season can make or break a retailer's year. But many brands still approach Black Friday, Cyber Monday, and year-end shopping periods as isolated campaigns rather than enterprise-wide moments that test every part of the customer experience.

That approach is becoming increasingly risky.

According to SAP's 2026 Global Engagement Index, 75% of consumers are frustrated by disorganized brand experiences, while 82% say a disappointing brand interaction causes them to disengage.

At the same time, 78% of brands believe AI will be essential for retaining customers in the coming year. The challenge goes beyond making AI investments, though; it lies in whether brands can connect customer insights, business data, and operational signals well enough to act on them.

Meet the experts

Ross Williams is a leader in product strategy at SAP, with a background in retail customer experience at Tesco and N Brown, where he managed platform migrations and peak-trading readiness for high-volume consumer brands.

Michelle Grant works across enterprise technology and consumer industries at SAP, translating market research and customer insights into digital transformation strategies.

Here's what they had to say about holiday retail marketing strategies.

1. What’s the most important strategy or tactic brands should do to prepare for a successful Black Friday and Cyber Monday season, and why?

Ross Williams: "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.”

What does that preparation actually look like? “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."

Michelle Grant: "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."

2. Where do you see AI having the biggest impact during the holiday shopping period this year?

Ross Williams: "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.”

Michelle Grant: “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."

3. The Autonomous Enterprise concept is gaining momentum. How should brands be planning to take advantage of this shift ahead of the holiday season?

Ross Williams: "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 crafting better engagement strategies, exploring new markets, and improving customer experiences."

Michelle Grant: "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."

4. What’s a common mistake brands make during holiday planning that could easily be avoided?

Ross Williams: "Many holiday problems are predictable. That’s why 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'll have to solve later. Holiday periods expose operational weaknesses very quickly, so preparation matters more than last-minute execution."

Michelle Grant: "One of the most common mistakes is underestimating the importance of transparent communication about product delivery. 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.”

5. How can brands turn holiday shoppers into loyal customers?

Ross Williams: "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."

Michelle Grant: "Retailers spend enormous amounts of money acquiring customers during the holidays. So, brands must think well beyond that first conversion. Every acquisition strategy should include a retention strategy. Otherwise, marketers are forced to start from zero again next season."

Ready for peak season? 3 keys to success

1. Connect your holiday marketing strategy to operational reality: Before launching campaigns, validate that inventory availability, fulfillment capacity, shipping timelines, loyalty offers, customer service staffing, and promotional plans are aligned. Every customer promise should be backed by operational truth.

2. Identify the business signals that should trigger action: Determine which customer and operational signals should influence real-time engagement. This could include low-inventory alerts, product demand spikes, abandoned carts, loyalty milestones, delivery delays, or changes in campaign performance. Then decide which actions require marketer approval and which can be automated. Make sure that you have already defined these workflows before peak season begins.

3. Build retention journeys before acquiring customers: Now is the time to design post-purchase experiences. Create journeys focused on second purchases, loyalty program enrollment, replenishment reminders, subscriptions, referrals, and personalized recommendations.

Download the Holiday Readiness Guide to learn more about using customer data, AI, automation, and real-time engagement to deliver exceptional holiday experiences, improve operational efficiency, and build customer loyalty that lasts long after the holiday season ends.

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