Retail Peak Season Chaos, Meet Your Match: Smarter CX Strategies That Work

Let’s talk about the retail peak season. You know, the make-or-break stretch where shoppers flood stores and websites, customer expectations skyrocket, and your systems are pushed to the limit.

If this gives you slight heart palpitations, you’re not alone. But don’t worry, we’ve got your fix.

Retail Dive recently hosted an eye-opening webinar, “Give Customers What They Want During Peak Seasons: An Unbeatable, Easy-to-Use Experience,” featuring two experts who live this reality: Michelle Kelly, 8x8’s Retail Vertical & Solution Marketing Manager, and Huw Fielding, Director of IT at Southampton Football Club.

If you’re an IT or CX leader prepping your tech stack and your team for the holiday rush, this session is your new playbook. Here’s a taste of the strategies they shared.

Why silos sink peak season (and how unified data fixes it).link to this section

The pressure of peak season exposes cracks in your systems. Contact centers drown in order queries. Store staff can’t see what’s happening online. E-commerce teams don’t know what’s happening post-sale. The result? Customers repeat themselves, get bounced between channels, and lose patience fast.

Michelle nailed it:

“Your stores don’t necessarily know what’s happening in your contact center... but when you unify all that data together, you have a full picture.”

Michelle Kelly

Retail Vertical & Solution Marketing Manager, 8x8

Huw added that without shared visibility, even loyal fans can feel “disconnected and anxious” during big-ticket transactions.

Unified data is more than an IT upgrade; it’s the foundation for delivering consistent, seamless customer experiences.

How automation and AI support retail teams during peak demand.link to this section

More customers. More questions. Less time. That’s the peak season equation, but it doesn’t add up without AI and automation.

But here’s the piece that some teams miss: automation isn’t here to replace people—it’s here to help them shine. Michelle framed it perfectly:

“Think of AI tools as giving every team member a personal coach, serving up product answers, policy reminders, or step-by-step guidance when they need it most.”

For Huw’s team, this was a lifesaver during seasonal staffing spikes:

“We’ve got lots of temp staff... so the use of AI and automation gives them access to the info they need to deliver the same great experience as someone who’s been here ten years.”

Huw Fielding

Director of IT, Southhampton Football Club

This is practical retail AI, helping your contact center scale with confidence while keeping the human touch.

Security and compliance: The non-negotiables.link to this section

AI and automation can supercharge retail CX, but they also raise new risks. Michelle cautioned:

“These are real worries, especially as the tools become a lot more powerful... Be sure that the automation tools you choose meet the same standards as your traditional systems.”

From PCI compliance to GDPR, data security has to remain central if retailers want to earn trust while they scale.

Start small, scale smart: Practical steps for retailers.link to this section

The good news: you don’t need to overhaul your entire tech stack to see results. Huw’s advice?

“Find some problems. They don’t need to be big. Start with something tangible that has value and tackle that straightaway.”

Michelle reinforced the point: AI isn’t plug-and-play magic, but when you tie it to clear goals—reducing call queues, speeding up agent training, or eliminating “Where’s my order?” tickets—you build momentum that carries you through the holiday season and beyond.

The payoff: Customer experiences that feel like a win.link to this section

When silos are eliminated, automation supports your staff, and security remains tight, you create the conditions for something every retailer is chasing: effortless, personalized customer experiences that drive loyalty.

Huw summed it up:

“We make sure that every individual feels valued based on what they’ve done before... and make sure that’s a really nice experience.”

That’s the real goal: not just surviving peak season, but creating the kind of CX that keeps customers coming back year after year.

Ready for the full playbook?link to this section

What you’ve read here is just a teaser. The on-demand webinar goes further, showing you how to:

• Put automation to work for your customer-facing teams.
• Connect and unify data for instant insight.
• Handle surges without burning out systems or staff.
• Choose the right tools before expanding your tech stack.

Don’t stop at the highlights. Watch the full webinar and see how leading retailers deliver unbeatable, easy-to-use experiences, no matter how chaotic the season gets.