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 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.

Retail e-commerce sales in the United States from 1st quarter 2009 to 2nd quarter 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.

Holiday shopping plans among consumers in the United States from 2015 to 2021 graph

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.

More Stories Like This:

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?

Follow us on social media for the latest updates in B2B!

Image

Latest

resilient leadership
How The Gentlemen’s Circle Is Redefining Resilient Leadership Through Accountability, Service, and Connection
October 31, 2025

On this episode of the Through the Storm podcast, Dr. Travis Hearne once again talks to CEO, leadership educator, speaker, fitness professional and retired Marine, Marc Rodriguez, a man whose career embodies resilient leadership. Rodriguez, who first appeared on the show to share his journey from the Marine Corps to a CEO, returns to…

Read More
radio expedition
Into the Icy Unknown: Ironman Triathlete Dennis Ward Leads a Bold Radio Expedition to One of Earth’s Most Isolated Places
October 30, 2025

Few places on Earth are as remote—or as thrilling—as Bouvet Island. Located deep in the South Atlantic Ocean and often battered by fierce winds and icy seas, it’s one of the most isolated spots on the planet. Reaching it requires months of planning, physical endurance, and a daring spirit. For amateur radio operators, however, Bouvet…

Read More
Greenland Energy Company Is Leading Responsible Oil Development in Greenland’s Jameson Land Basin
October 30, 2025

The global conversation around oil is evolving—shaped by the forces of energy transition, geopolitical tension, and accelerating technology. Even as the world races toward decarbonization, demand for reliable, dispatchable energy continues to climb. Oil and gas together still supply just over half of global primary energy, underscoring their enduring role in the world’s power…

Read More
luxury resale
How Luxury Resale Became Big Business: Inside Fashionphile’s Playbook
October 30, 2025

Luxury retail is in the midst of a reinvention. Circular fashion has moved from trend to transformation, reshaping how consumers perceive value, ownership, and access. According to the 2025 BCG × Vestiaire Collective Resale Report, the secondhand fashion and luxury market now totals $210 to $220 billion globally and is projected to reach $320…

Read More