Skip to content
‹ Back to IndustriesRetail

Cyber Monday Will Be the Big Test for Retailers’ Ecommerce Strategies

The holiday shopping season gets its first big test this weekend with Black Friday deals and the welcomed-by-retailers resurgence of in-store shopping and deals. Even if consumers are looking to hit stores bright and early on Friday, the last almost two years of ecommerce acceleration and validation have changed retailers’ omnichannel strategies. Retailers will…

This story was produced through MarketScale. See how Retail teams put it to work with Sales Enablement.

·
Share
Cyber Monday Will Be the Big Test for Retailers’ Ecommerce Strategies

Free workspace

Turn your Retail expertise into content.

Record interviews, organize footage, and write with AI on a free trial of the MarketScale platform for qualifying companies. No demo required, no credit card.

Try it Free

The holiday shopping season gets its first big test this weekend with Black Friday deals and the welcomed-by-retailers resurgence of in-store shopping and deals. Even if consumers are looking to hit stores bright and early on Friday, the last almost two years of ecommerce acceleration and validation have changed retailers’ omnichannel strategies. Retailers will get a second big test on their online adaptability at the start of the week with Cyber Monday.

Since Q1 of 2009, U.S. retail ecommerce sales have been climbing. Naturally, when the pandemic hit in Q1 of 2020, online sales spiked, by as much as $50 billion according to the U.S. Census Bureau. And after some plateauing and fluctuation, those sales numbers continue to climb through at least Q2 of 2021.

As for consumer shopping habits specifically for the holiday season, the share of consumers planning to shop online remains greater than those planning to shop in-store, 57% vs. 43%, according to PwC. Though this is a slight decrease compared to 2020’s holiday shopping, it’s still reason enough for retailers to prioritize their online presence from Black Friday though Christmas.

With this more permanent omnichannel demand, have strategies for developing an exciting ecommerce offering for Cyber Monday shifted since 2019 & 2020? And especially as a smaller boutique retailer trying to compete with big box online deals, what marketing or customer service tactics will help retailers stand out during Cyber Monday? We sourced two thought leaders for perspective on how to leave a unique footprint online during our Black Friday Roundtable: DeAnna McIntosh, Executive Director & Co-Founder of The Affinity Group and Bryan Eisenberg, Co-Founder of BuyerLegends.

“It’s a struggle. Every retailer needs to find ways to connect with the human side of the equation, why they’re in the business, why they’re doing this, and use all the channels available to us today to put out that content and let us feel comfortable with the people behind the business,” Eisenberg said.

“They could have done little fun games and surveys and little ways to poke at their customer and say, ‘Who are you going to be shopping for this holiday season?’ and ‘We’re curating a special collection and we want to make sure that it speaks to them,’ so they can start to get ideas and actually curate collections for those people. Just make it a no-brainer,” McIntosh said.

For the full Black Friday Live Roundtable, where Eisenberg and McIntosh give a retail supply chain state of the union, dig into more granular supply chain trends impacting retail outlook, and offer strategies for ecommerce success, click here or head to our Events tab.

Holiday Demand Forces Retailers to Get Creative with Hiring Strategies

Retailers Invested in Fulfillment and Demand Forecasting Post-Pandemic. Will it Pay Off for Black Friday?

Your experts belong here

Every story in MarketScale Retail starts with a company putting its merchandising leads, store operations teams, and category managers on the record. Buyers are already reading this topic. The only question is whose experts they find.

Category buyers trust operators, so your merchandising leads shorten the distance between first search and first call.

Book DemoSee how it works15 minutes, straight to a calendar.
B2B Weekly

The week in Retail, and sixteen other industries, every Monday.

Ten stories, one-line takes, five minutes. Free.

Retail: are you visible to AI?

Before they reach out, Retail buyers ask AI engines which vendors to trust. Explore how your experts, customers, and partners can become useful content for buyers and AI search.

Free Trial

You just read one Retail expert. Your company is full of them.

This article was produced through MarketScale. The same platform turns your merchandising leads, store operations teams, and category managers into the articles, video, and social content Retail buyers are searching for. Start a free trial and see it with your own people. For qualifying companies, no credit card, no demo required.

NPS +73 · 1,000+ creators · 38+ countries

What your free trial includes

Hands-on access to the MarketScale platform
Media requests to your crowd, remote recording, AI writing tools
No demo required. No credit card.
For qualifying companies. Company confirmation required.

More Retail Insights

Grocery Vision AI takes the blame for failures the network underneath causes

Grocery Vision AI takes the blame for failures the network underneath causes

Vision AI and automation failures in grocery stores often stem from inadequate network infrastructure rather than the technology itself. Operators must audit network capacity before deployment and build standardized architecture that scales across multiple locations, as pilot successes rarely translate to fleet-wide reliability without proper infrastructure planning.

  • 01Network instability can cause AI systems in grocery stores to perform poorly during peak hours.
  • 02Perceived Vision AI failures are often misattributed when the network underneath is the more likely cause.
  • 03Customer frustration can increase when self-checkout lanes experience delays or disruptions.

Oct 6, 2026

Retail tech rollouts slip when nobody plans for the live store

Retail tech rollouts slip when nobody plans for the live store

Retail technology rollouts often slip when plans ignore the operating store itself. By piloting in low-revenue locations, reserving recovery time before opening, coordinating hardware and field resources, and standardizing store types upfront, retailers can protect opening dates and customer experience while deploying new systems.

  • 01Pilot technology in low-revenue stores where failure costs least revenue, not in flagships, to surface conversion problems before high-impact rollouts.
  • 02Build cutover schedules with dedicated recovery time before store opening; a failed cutover at 5 a.m. with no margin forces either broken equipment or late opening.
  • 03Coordinate hardware procurement, staging, and field technician availability as a single constraint; delays in any handoff push back every dependent store visit.

Oct 6, 2026

Amazon says Prime delivery can run on merchants’ sites at no added MCF cost

Amazon says Prime delivery can run on merchants’ sites at no added MCF cost

U.S. merchants using Amazon’s Multichannel Fulfillment can offer Prime delivery on their own websites at no cost beyond standard fees, Amazon says. Amazon verifies Prime membership after checkout, so shoppers don’t log in to Amazon and merchants keep their own checkout while handling returns and customer service. Separately, Amazon says its MCF Preferred Pricing Program can lower fulfillment fees 15% to 25% for eligible FBA sellers during their first six months, with benefits continuing through a 12-month program.

  • 01The Prime badge now costs an MCF merchant nothing beyond the fulfillment fee it already pays, and the checkout page stays the merchant's own.

Sep 26, 2026

Explore More Retail Insights

Read more expert perspectives from across Retail.

Browse Retail Hub

For B2B teams

Your experts could be publishing here

Stories like this one run on content MarketScale captures from real practitioners. See how your team's expertise becomes coverage in Retail and beyond.

Book a Demo

Or call us. No forms required. We pick up. 214-945-2512