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

Open questions in agentic commerce extend beyond the AI model

Agentic commerce raises questions beyond an agent’s ability to compare prices: what an agent is permitted to do, who is responsible when an agent-initiated purchase goes wrong, and how machine-initiated transactions move safely across merchants, banks and payment networks. Mastercard's Sabrina Tharani frames the shift as a new interface for commerce rather than a separate channel.

  • 01Agentic commerce now turns on three questions the AI can't answer for itself: what the agent may do, who is responsible when it errs, and how its transaction moves between merchant, bank and network.

Sep 26, 2026

Grocers matching store prices on Instacart grew 10 points faster, Instacart says

Grocers matching store prices on Instacart grew 10 points faster, Instacart says

Instacart says it named five grocers as "among" this year’s no-markup adopters, including Grocery Outlet. Using its internal data through Q2 2026, Instacart reports no-markup retailers grew 10 percentage points faster than those charging a markup. Participating grocers also get placement in a dedicated in-app "no markups" tab.

  • 01On Instacart, matching store prices earns a yellow banner and placement in a filtered "no markups" tab; Instacart’s internal data through Q2 2026 shows no-markup retailers grew 10 percentage points faster than those charging a markup.
  • 02The 10-point gap compares grocers that chose parity with grocers that didn't, so it can't separate the effect of pricing from the kind of retailer that opts in first. The sharper question is how retailers with similar baskets fared before and after they switched.
  • 03Parity covers item prices only. Service fees still apply, so the app price-to-shelf-tag comparison evens out while convenience charges remain their own line on the receipt.

Sep 26, 2026

Suja's CEO says wellness drinks win in produce, not center store

Suja's CEO says wellness drinks win in produce, not center store

Suja Life CEO Maria Stipp argues better-for-you beverages win or lose based on store placement, with the produce department offering an advantage over crowded center aisles by signaling freshness alongside organic produce. She pairs this with packaging guardrails around organic, low sugar and function, plus a commitment of roughly 10% of net revenue to full-funnel marketing aimed at building trust.

  • 01Suja’s cold-pressed, HPP-treated juices can move from partner farms to shelf in eight days, a cadence Stipp says matches how produce buyers operate.
  • 02Average retailers carry only low-teens SKUs even as Suja reaches 37,000 retailers and 400,000+ distribution points; Stipp says closing the SKU gap in existing accounts is a bigger growth priority than chasing new logos
  • 03Suja allocates roughly 10% of net revenue to full-funnel marketing—unusual in the next-gen category—to drive awareness and conversion through omnichannel tools

Sep 23, 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