Skip to content
MarketScale
‹ 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

Get featured

Want MarketScale to feature Retail?

Book a 15-minute demo and we'll map your Retail expertise to the content buyers are searching for.

Book a demo

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.

Get your team featuredSee how it works15 minutes, straight to a calendar.

Follow Retail Insights

Get new expert content in your inbox.

Retail: are you visible to AI?

Before they reach out, Retail buyers ask AI engines which vendors to trust. See how AI describes your company today, and where competitors show up instead.

Free workspace

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. Create a free workspace and see it with your own people. No credit card, no demo required.

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

What you get, free

Your own MarketScale Studio workspace
One video edit a month, on us
AI writing, editing, and publishing tools
In-platform coaching to learn the system

More Retail Insights

Marketplaces are growing twice as fast as traditional online shops, and every major platform just made a move

Marketplaces are growing twice as fast as traditional online shops, and every major platform just made a move

Online marketplaces are expanding at double the rate of traditional online stores. Major platforms like eBay, TikTok, and DoorDash are making strategic moves to strengthen their market positions, such as acquisitions and testing new services.

  • 01Online marketplaces are growing twice as fast as traditional online shops.
  • 02eBay has acquired the marketplace Depop.
  • 03DoorDash has received FAA approval for drone deliveries.

Aug 13, 2026

Agentic AI is rewriting retail operations, and Salesforce's Brunello Cucinelli deal shows how fast

Agentic AI is rewriting retail operations, and Salesforce's Brunello Cucinelli deal shows how fast

Salesforce's implementation of its Callimacus AI at Brunello Cucinelli demonstrates a rapid evolution in the retail sector's operational strategies. The adoption of agentic AI provides a new way for enterprise retailers to enhance their processes and scale efficiently.

  • 01Salesforce's Callimacus AI is being deployed at Brunello Cucinelli.
  • 02Agentic AI is transforming retail operations on an enterprise scale.
  • 03The adoption of AI in retail is accelerating operational efficiency.

Aug 13, 2026

Bed Bath & Beyond's rebound and eBay's Q2 gains signal a structural shift in how retail brands recover online

Bed Bath & Beyond's rebound and eBay's Q2 gains signal a structural shift in how retail brands recover online

Bed Bath & Beyond announced its rebranding to Neighborhood Intelligence following Q2 revenue growth, signaling a strategic shift. eBay reported an increase in Gross Merchandise Volume, showcasing its continuous growth even without considering its acquisition of Depop. These developments suggest a structural shift in how retail brands are recovering online.

  • 01Bed Bath & Beyond is rebranding to Neighborhood Intelligence after Q2 revenue growth.
  • 02eBay increased its Gross Merchandise Volume in Q2 before factoring in Depop's acquisition.
  • 03There is a structural shift in how retail brands are recovering online.

Aug 12, 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 15-minute demo

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