Vermont Retailers Aim to Cash in on Cyber Monday

Even with the year-round interest in online shopping, Cyber Monday remains relevant, businesses insist

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Cyber Monday remains an important focus for retailers, businesses insist, even as online shopping has become a year-round activity — especially during the pandemic.

“I feel like Cyber Monday has become almost a cultural event,” said Cassie Clayton of Vermont Teddy Bear in Shelburne.

Between bears, the company’s PajamaGram label and its new official line of Bernie Sanders mittens inspired by that famous meme of the senator in his on Inauguration Day, Vermont Teddy Bear said its online orders this year are poised to top those from 2020.

That was a record year itself, when shoppers were doing more from home because of the pandemic, the company noted.

“People have not stopped shopping online,” Clayton said. “And days like Cyber Monday are just that much bigger this year.”

Jen Ellis, the woman behind the now famous mittens, says she is putting three new pairs of Bernie Sanders mittens up for auction.

For Cyber Monday, Vermont Teddy Bear was offering free gifts with certain levels of purchases.

Tom Funk, a digital marketing professor at Champlain College, said he bets supply chain challenges have likely shifted many shoppers’ focus this season.

“Consumers were shopping really aggressively in August, September, October,” Funk pointed out in an interview.

Along with that pre-planning for holiday buying, Funk suggested that product availability, not simply discounts, will matter to shoppers this year, perhaps to the benefit of brick-and-mortar stores and online sellers they are confident can deliver on-time.

“When they see something they know they want to put under the tree, I think they snap it up rather than waiting for a better price,” Funk said of shoppers.

At Lenny’s Shoe & Apparel in Williston, the Cyber Monday challenge was how to stand out, said e-commerce specialist Ryan Sogge.

He acknowledged how crammed everyone’s email inboxes are with incentives from other companies. Sogge’s strategy was to give people something they truly want, he said, in the form of one-day sale prices on several of the most popular brands at Lenny’s.

It seems to have worked.

“This is definitely our biggest shipping day of the year,” Sogge said. “This morning, when I sat down at my desk at 9, there were 35 orders waiting for me. On a typical day, there might be five.”

Erin Sigrist, the president of the Vermont Retail & Grocers Association, pointed out Cyber Monday is no longer the territory of just the nation’s biggest names in retail — not after COVID-19 left mom-and-pop businesses with no choice but to get into the e-commerce game last year.

The Black Friday shopping madness might be over, but Cyber Monday is up next, and scammers know you're ready to spend -- that's why experts say you're more likely to fall victim this time of year. An MIT cyber security expert says you need to watch out for any ads offering discounts and other savings, especially if they want your personal information.

“Now that they’ve made the first step, we will continue to see more small retailers participate in Cyber Monday,” Sigrist predicted.

Back at Vermont Teddy Bear, it could combat supply chain anxiety by highlighting online how its bears and Bernie Mittens are stitched in Vermont, Clayton said, and by assuring a Cyber Monday purchase would be shipped on Tuesday — in plenty of time for Christmas.

A portion of sales from the official Bernie Mittens benefit Make-a-Wish Vermont.

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