How IT helps avoid holiday season mishaps

It’s right about now that Christmas music starts playing in stores, even though the biggest holiday shopping days are still months away. For retail IT teams, that soundtrack is one cue that it’s the season to prep—operationally—for the crunch of activity to come.

This year may be more hectic than ever. “There’s just a tremendous amount of uncertainty right now,” says Gwen Morrison, partner at Retail Cities and former CEO of WPP’s global retail practice. “That kind of chaotic disruption has put so many unknowns out there.”

Morrison points to a combination of supply-chain and tariff uncertainty, rapidly changing policy conditions, consumer anxiety, and potential pressure on seasonal labor. That uncertainty raises the value of real-time operational visibility. “Where is everything now?” is the critical question, she says, not only for goods and materials moving through the supply chain, but for the devices, systems, and services employees rely on to serve customers. 

AI is helping retailers absorb the surge, but not without creating new pressures behind the scenes. While 59% of retailers say AI has significantly improved their ability to handle peak demand, according to Freshworks’ latest Customer Service Benchmark Report 2026, separate research finds that 81% of IT leaders in retail and hospitality say managing AI-related complexity has increased their teams’ workload.

For retail IT, holiday readiness means keeping systems, assets, and employees prepared for demand spikes. Here’s how three retailers are building the visibility, service foundations, and customer-support capacity to manage pressure in holiday style.

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Keeping track of all those mobile devices

In anticipation of a flood of customers, retailers bring on numerous seasonal workers and, increasingly, equip them with mobile tools to locate inventory, answer questions, and fulfill orders. That’s pressure on IT to know not only what assets it has but also which services could be affected if one changes or fails.

New Balance replaced disconnected tools with Freshservice and Device42's platform automatically discovers and maps every component of their hybrid infrastructure, giving the company comprehensive asset visibility.

"We wanted to have a single source of truth for all of our inventory assets to be inventoried and also have the transparency and the visibility of everything that exists in our network," says Markus Gaulke, platform manager for the IT service desk. His team now supports more than 5,000 tickets each month across 133 agent groups, with the platform used by IT, HR, facilities, and loss prevention. In the holiday rush, an accurate CMDB helps IT assess the impact of a change before a seemingly isolated issue reaches stores or employees.

Read more: New Balance steps up IT operations

Streamlining employee support needs

During the five-day sprint from Thanksgiving to Cyber Monday, seasonal and permanent employees cannot afford to hunt through an org chart for help. They need a single “front door” through which to get resources and support for any access, device, delivery, payroll, or store operations issue, and the right team needs to receive it quickly.

Bensons for Beds helps employees get what they need through Freshservice, which is used in the HR, finance, marketing, warehouses, and distribution departments. Workspaces gives each department a tailored experience on a shared foundation, and a way to keep sensitive data contained. Freddy AI has also reduced average response and resolution times. The holiday payoff: a larger, more distributed workforce can find what they need through one interface rather than lose time navigating disconnected departments.

Read more: Bensons for Beds delivers exceptional IT service with Freshservice

Making time for higher-level inquiries

When holiday shopping compresses into a few deal-heavy days, customer questions pile up just as quickly: Is it in stock? Will it arrive in time? Which product do I need? Hobbycraft was managing nearly 250,000 customer inquiries with a combination of a shared Outlook inbox, separate phone tools, social platforms, and web forms. Agents lacked a single customer view, and routine delivery and stock questions consumed time that could have gone to more complicated requests.

Hobbycraft unified email, phone, social, and web support with Freshdesk, Freshcaller, and Freshchat, then added Freddy AI for self-service and agent assistance. Customer satisfaction increased 25%, response times fell 30%, and agents resolved 82% of tickets at first contact. Freddy AI chatbots now handle up to 30% of inquiries. Holiday season is busy at Hobbycraft, but now specialist support staff have more bandwidth to spend talking crafts with customers.

Read more: Hobbycraft retools customer service