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

Larry North
Resilience, Reinvention, and the Relentless Pursuit of Growth: Larry North’s Journey from Fitness Icon to Private Equity Leader
February 20, 2026

Entrepreneurship is being glamorized in real time. Social media highlights overnight wins, AI tools promise instant scale, and private equity is reshaping industries at a rapid clip. Yet behind every “success story” is something far less flashy: failure, adaptability, and the discipline to keep going when life hits hard. According to the U.S. Bureau…

Read More
Consulting
Consulting Reframed: Perspective, Leadership, and Impact Beyond the Client
February 19, 2026

As organizations navigate accelerating digital transformation, tighter margins, and increasing organizational complexity, the role of consultants is being re-examined. Today’s most effective consulting leaders are no longer valued simply for delivering projects, but for bringing outside perspective, cross-industry insight, and the ability to lead through ambiguity. Most large organizations today are not short on…

Read More
comedy
Laughter as a Service: How Comedy Can Power Trust, Teamwork, and Career Growth
February 19, 2026

Comedy might be the most underused business skill in your toolkit… In a world of back-to-back Zoom calls, Slack threads, and AI-generated everything, real human connection can start to feel like an afterthought. We’re moving faster than ever, but sometimes we’re listening less, reacting more, and missing the small moments that actually build trust. The…

Read More
founder-led brand
The Art of Evolution: Leading a Founder-Led Brand Into Its Next Chapter with Mary Beth Sheridan
February 19, 2026

For many retail brands, growth today isn’t just about innovation — it’s about keeping pace with customers whose expectations are evolving in real time, led by younger generations who expect brands to reflect their values and show up with cultural relevance. In fact, recent research from MG2 found that the overwhelming majority of Gen Z…

Read More