Why it matters:

  • Businesses that tap into support for Small Business Saturday with their marketing messages see greater rates of responses, with “Shop Small” email campaigns averaging open rates of 45%.
  • Creating a cash flow forecast and having a holiday cash reserve can help small businesses be ready to take advantage of peak sales periods.
  • For merchants, it’s key to remember the power of a simple “hello”: Not being greeted, or made to feel welcome, when they walk into a small business is a top consumer complaint.

Small Business Saturday, held on the Saturday after Thanksgiving, which falls this year on November 29, is a day when Americans are primed to shop local and support their neighborhood businesses. For many small businesses, it also marks the start of their busiest and most profitable month of the year. 

But small business owners often don’t have the resources available to big businesses to plan for peak times. CO—reached out to four experts—a fintech executive whose company makes accounting easier for small businesses; a consumer insights specialist for one of the largest consulting and advisory firms; a marketing and messaging expert; and a consultant who has worked with thousands of small businesses over the past 31 years—for actionable tips small businesses can use to prepare for and optimize Small Business Saturday and the holiday season. 

Dave Charest, Director of Small Business Success at Constant Contact: ‘People want to shop small. Embrace who you are’

Small Business Saturday is a unique opportunity for local businesses to capitalize on one of their biggest assets, Dave Charest, Director of Small Business Success at marketing company Constant Contact, told CO—. That asset, Charest said, is “people want to shop small.” 

Constant Contact studied more than 12,000 email campaigns sent to customers during this summer’s Amazon Prime Day sales and found that messages with “Shop Small” and “Shop Small Business” had the highest open rates and click-through rates. By contrast, messages highlighting phrases like “Mega Sale” had the lowest open and click rates. 

“What we’re seeing is that Shop Small messaging is really resonating with people,” Charest said. 

“People want to shop small,” he said. “As a small business owner, often times you want to position yourself to look bigger than you actually are. Really what you should be doing is just the opposite. Embrace who you are,” he said. 

Charest recommends that small businesses make the most of Small Business Saturday and holiday season with these strategies:

  • Let consumers know how you support your local community. “Highlight people in the community that your product or your service or your business cares for,” he said. “People appreciate those connections and want to feel part of that community.”
  • Three’s the charm. For marketing messages about special sales or events at your business, Charest recommends sending at least three messages—the first timed several weeks in advance to announce the event, the second to remind customers of the event, and the third to serve as a last-chance message sent the day before or day of the event.
  • For email messages to your customer list, “Write as if you’re talking to one person,” he said. Lean into the personal relationship customers have with you as a local small business owner, and make the messages read like a personal note from you.
Highlight people in the community that your product or your service or your business cares for. People appreciate those connections and want to feel part of that community. Dave Charest, Director of Small Business Success, Constant Contact

Raj Bhaskar, CEO of fintech company Tight: ‘Create a cash flow forecast so you can make smart decisions about holiday investments’ 

Raj Bhaskar, CEO of Tight, which provides embedded small business accounting software that’s used by 1.3 million small businesses, said it’s critically important for business owners prepare for Small Business Saturday and the holiday season by reviewing sales and expenses from last year’s holiday season and knowing when they can expect to see sales and costs spike.

One sure thing, Bhaskar told CO—, is that in good economic times as well as bad, “there’s always a holiday spike.” Businesses that are prepared can take advantage of the holiday sales spike, both on Small Business Saturday and during the rest of the season.

He recommends that small businesses:

  • Create a weekly cash flow forecast for the holiday season through January, outlining expected revenue and expenses.
  • Start the season with a separate holiday cash reserve to cover gaps between expenses and revenue. “Even $500 to $1,000” can help, he said.
  • Plan for the post-holiday period by setting aside a fixed portion of holiday revenues to cover expenses during the slower months of January and February.

[Read more: 3 Founders on the Critical Business Decisions That Proved Pivotal to Success]

Bob Phibbs, CEO of The Retail Doctor, a retail consultancy: ‘We do business with people who make us feel we matter’

Bob Phibbs, CEO of The Retail Doctor, has advised thousands of small business owners in his 31 years as a retail consultant and knows this holiday season presents unique challenges. 

“You can blame the economy …which changes every day — you can’t control any of that. The only thing a business can control is the way that they engage a stranger,” he told CO—.

“The more you don’t realize we do business with people who make us feel we matter, the more you’re going to complain,” Phibbs said.

His top tips for winning new customers on Small Business Saturday and throughout the holiday season include: 

  • Not being greeted in a store is the top customer complaint. “If you’re so concerned with tasks and busy work, you’re going to miss the fact that somebody walked in the door and you didn’t make them feel they matter, so they walked out,” Phibbs said.
  • Training your staff to welcome and engage customers is the best investment you can make. “If your staff can’t sell, your décor doesn’t matter,” he said. “If they can’t engage a stranger and suggest the right product and add on to it, you’re just a gallery, you’re not a business.”
  • If you host a holiday event, have a way to capture new customer information, such as a QR code on display in your store that links to holiday tips, or offers a customer will sign up for using their email address. “Often, when we have that traffic of people who are interested in your store, we don’t capture it,” he said.

Mike Daher, U.S. Consumer Industry Leader, Deloitte: ‘Use strategies to compete beyond price’ 

Audit, consulting, and advisory firm Deloitte has identified a key characteristic of this year’s holiday shoppers. Consumers, Deloitte reported this selling season, are looking for businesses that add value beyond the price of the item.

Small businesses are uniquely positioned to create added value for holiday shoppers, Mike Daher, Deloitte’s U.S. Consumer Industry Leader, told CO—. His top advice on how to do that includes:

  • During the holiday season, add-ons, such as gift wrapping, engravings, local delivery, or supporting a local charity, “are all really good strategies to compete beyond just price in this market,” Daher said.
  • Have good, better, best price options on display in your store. “Give people a perception that there’s a value option on the table in your location,” Daher said.
  • Ask customers for their feedback. People want to support small businesses, and being able to give advice helps them feel invested in the business, 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.

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