Expert Advice on How to Win on Small Business Saturday and Drive Holiday Sales

For many small businesses, Small Business Saturday has the potential to be their busiest day of the year—and if done right, can kick off a month of strong holiday sales. 

Not only is it a key revenue driver, but it’s a day when new customers are most likely to be introduced to a local business. For weeks before Small Business Saturday, which always falls on the Saturday after Thanksgiving, local and national business groups are promoting the event and urging Americans to “shop small.” 

That’s why it’s important to be ready for the big day. CO— reached out to four experts whose jobs are to help small businesses succeed. Here are their top, practical, actionable tips that businesses, no matter how small, can use to their advantage.

‘Turn browsers into buyers – without a single discount’

Bob Phibbs, CEO of retail consulting firm The Retail Doctor, and author of ‘The Sales Floor Problem’

Over the past 30 years, Bob Phibbs, CEO of The Retail Doctor consulting firm and creator of employee training program SalesRX, has helped thousands of businesses, large and small, learn how to engage with customers to boost sales. 

Phibbs describes what he does as helping businesses “turn browsers into buyers – without a single discount,” and he’s counseled Main Street store owners on how to turn Small Business Saturday crowds into returning loyal customers. 

This year, Phibbs is emphasizing both the timeless customer engagement tips that have been true for decades, but he has added an AI-specific tip for 2026.

His tried-and-true tips that remain important every year are:

• Make customers feel they matter the minute they walk into your store or business. “Everybody that comes in wants to be seen and heard,” Phibbs said. Not being greeted is the top customer complaint, he said.
• Don’t paint or obscure your store windows.  People like to be able look inside your store and see people, he said. Seeing people in the store will draw more people.
• Phibbs’ new tip this year is to use readily available AI tools to tell you how you can do things better. Phibbs isn’t talking about adopting a complicated AI platform. It can be as simple, he said, as taking any AI program, such as ChatGPT or Claude, showing it a PDF of your newsletter, your promo offers, your special event, and telling the AI: “You’re an excellent marketer. Grade this piece.”

“I guarantee you it will come back and the grade is probably D or C,” Phibbs said. “Then you say, ‘Now fix it.’”

“You can do that for your holiday help ads, your want ads. It’s a game changer,” he said.

The key point is to ask AI to grade what you’re doing, then fix it—not just use AI to create content. 

You can also ask AI to review your product assortment or your holiday shopping guide and “give me three other contrary gift ideas I didn’t think of,” Phibbs said. 

[Read more:  5 Key Consumer Insights to Turn Customer Engagement Into Sales on Small Business Saturday and During the Holiday Season]

‘People want to shop small, so use that to your advantage … offer something they can’t get at a big retailer’

Dave Charest, Director of Small Business Success at Constant Contact

Dave Charest has spent 15 years helping small businesses connect with customers at digital marketing company Constant Contact, and he has interviewed dozens of small business owners as a host of the award-winning Be A Marketer podcast. 

The number of consumers who say they prefer to “shop small” has nearly tripled over the past five years, Charest told CO—, but he noted that this year shoppers also are saying that inflation and financial worries may limit how much money they can spend at local businesses.

That means, Charest said, that small businesses “need to give people a reason to visit you on Small Business Saturday—something they can’t get at a big retailer, like a customized bundle, gift wrapping, or a sneak peek at something new.”

To bring customers to your business on Small Business Saturday and the rest of the season, Charest recommends:

• Businesses should start emailing customers about Small Business Saturday events and holiday deals in early November and plan a series of three pre-event emails, Charest said. “First, share what you are planning. Then remind them a week before. Finally, send a last-call email the day before or Saturday morning as people are deciding where to go.”
• “People want to shop small, so use that to your advantage,” Charest said, and lean into that when emailing customers. “Keep it human and specific,” he said. “Keep your subject lines light, for example, ‘Saturday is for the neighborhood. Come by for a chat.’ Write your emails like a note to your community, your friends, not a corporate press announcement.”
• Send a thank-you email the following week to everyone who visited your business on the big day. “This keeps your regulars connected and new customers coming back,” he said.

“The more reviews you have the better — reviews become currency’

Syed Ali, Co-founder and CEO of Pie, an AI marketing firm for SMBs

Syed Ali has spent the past 10 years talking to small business owners about their needs, first while working at Square, the tech company that created the mobile credit card reader that made it possible for many small businesses to accept credit cards, then at Toast, the point- of-sale system used by many small restaurants. 

He co-founded Pie just over a year ago because he said that the AI age has created new pressing needs for small businesses. Pie offers SMBs ways to increase their visibility on AI agents, as well as AI-aided marketing and a voice assistant that can handle calls after hours or during busy times. 

There are a number of easy things businesses should be doing this season to compete better in the age of AI – steps that don’t require big decisions or signing up for a new tech platform, Ali said.

This year, when more and more consumers are starting their holiday shopping and gift planning by asking an AI chatbot or agent something like, “Where can I find this gift?” or “Where can I get a massage gift certificate?” being discoverable by AI is key, Ali said. 

Tips that Ali gives Pie clients to improve discoverability include:

• Make sure your Google Business profile, your Yelp profile, and your Instagram or Facebook page are all updated. “Make sure there’s the right information on there—the right store hours, you have photos, [etc.],” Ali said.
• Encourage customers to leave reviews and respond to the reviews you get. “The more reviews you have, the better,” he said. “If you’re looking for a restaurant and you see one with 10 reviews and one with 1,000 reviews, you’re more likely to check out the one with more reviews. Reviews become currency.”
• Small businesses often don’t realize that they can add a booking link to their Google profile. “That’s less friction. Customers don’t have to call. They can hit ‘book immediately’ and it’s a frictionless flow to make an appointment. The more friction you add, the higher likelihood that a consumer is going to drop off.”
• Make sure you are adequately staffed for the holidays. “If you get a large influx of people and there’s a long waiting line, they’re not going to be happy. And that can lead to a negative review.”

Tap AI to tell compelling stories on product pages through rich text, lifestyle image carousels, and video

David Forsythe, Vice President, North America Seller Business, Amazon

When American Express launched Small Business Saturday in 2010, the primary focus was on Main Street stores that had been hurt during the Great Recession. 

This year, Amazon is making it easier for customers to shop small businesses, with a Small Business shopping destination, “plus social and creator-led storytelling that spotlights small business sellers and exciting and giftable small business deals,” David Forsythe, Amazon’s Vice President, North America Seller Business, told CO—.

For small businesses that sell online, Forsythe offered these suggestions to stand out on Small Business Saturday and drive holiday sales:

• Make your brand and products easy to discover. For example, “Amazon’s A+ Content lets brands tell compelling stories on product detail pages through rich text, lifestyle image carousels, and video. And with Amazon’s generative AI tools, sellers can quickly and easily generate captivating lifestyle imagery and more engaging, informative listings,” Forsythe said.
• “The sellers who do well during peak tend to prepare early and lean on the tools available to them. Prepare your inventory ahead of demand,” he said, adding that Fulfillment by Amazon helps sellers get products delivered reliably during the busiest time of the year.
• “Leverage innovative new tools,” Forsythe said. Small business sellers can use Amazon’s Seller Assistant tool “before, during, and after an event, to set up deals, prep and monitor inventory, and compare their sales with last year’s results,” he said. Seller Assistant also lets sellers test different strategies and identify growth opportunities, he said.

CO— aims to bring you inspiration from leading respected experts. However, before making any business decision, you should consult a professional who can advise you based on your individual situation.

CO—is committed to helping you start, run and grow your small business. Learn more about the benefits of small business membership in the U.S. Chamber of Commerce, here.