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

Ulta is marketing to AI agents and shoppers

Ulta is marketing to AI agents and shoppers

Ulta segments customers by motivations (not just demographics) and uses non-purchase signals like social activity and store behavior to inform personalization and messaging.

  • 01Ulta treats AI agents as new voices it cannot control, similar to how it manages influencer and store associate recommendations, shaping what agents know rather than what they say.
  • 02Ulta uses motivation-based segmentation (beyond demographics) and non-purchase signals like social activity and store visits to inform personalization, with loyalty data as a foundation as it explores what AI agents need.
  • 03Ulta says research shows young consumers who use AI tools and chatbots still crave coming into stores and are more likely to visit, raising the pressure on stores to earn the trip.

Nov 7, 2026

Amazon lets shoppers text Alexa for Shopping to place orders and track prices

Amazon lets shoppers text Alexa for Shopping to place orders and track prices

Amazon is rolling out text-message access to Alexa for Shopping, its AI shopping agent, starting with a small group of U.S. customers by invitation. The agent can search, compare, buy items, track prices, reorder products, and send alerts across text and other Amazon platforms.

  • 01Texting with Alexa for Shopping rolls out to a small group of U.S. customers by invitation, expanding to millions in the coming weeks
  • 02The agent can reorder items, set up weekly grocery orders, watch for price drops, show up to a year of price history, and send new-release alerts
  • 03Requests started over text carry over to the Amazon Shopping app, Amazon.com, and Alexa-enabled devices

Nov 6, 2026

Small retailers rethink shipping fees as holiday shipping costs climb

Small retailers rethink shipping fees as holiday shipping costs climb

The National Retail Federation expects holiday retail sales to rise 4.2% to $1.01 trillion, but higher fuel prices and carrier holiday surcharges are raising shipping costs. Evie Pearl Handmade's owner now pays nearly $6 per package and is considering raising her shipping fees for the first time in six years. A New Jersey clothing founder began charging customers for return shipping this week. Larger retailers with dedicated contracts are better insulated for now, though Amazon reported an 11% rise in third-quarter shipping expenses.

  • 01NRF expects holiday retail sales to rise 4.2% to $1.01 trillion.
  • 02UPS, FedEx and USPS have added holiday surcharges that run through the end of the season.
  • 03One small seller's average label rose from around $4.50 last year to nearly $6 last month, and she is considering raising her shipping fees.

Nov 6, 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