Your holiday season starts on your website, and this year it is 27 days long

Sixty percent of online holiday shoppers say they will start on a retailer or brand website this year, up from 51 percent last October (Bain & Company, 2026 Holiday Shopping Outlook). Amazon still leads at 71 percent, but the direction is clear. Shoppers are arriving at your front door earlier, and the front door is a web page.

That matters more than usual in 2026, because the season is short. Small Business Saturday falls on November 28, which leaves 27 days before Christmas (Main Street America, September 2026). It is one of the tightest holiday windows in years, and a shop that waits until the week of Thanksgiving to sort out its website, its hours and its posting will be doing it in the middle of the rush.

The money is there, and most of it still walks in

Bain forecasts US holiday sales will top $1 trillion for the first time, growing 4.5 percent, with roughly 70 percent of that total still happening in stores. Nonstore sales are expected to grow 9 percent, against 2.5 percent for in-store.

Read that carefully. Most of the money still crosses a physical threshold. But the decision about which threshold to cross is increasingly made on a screen before anyone leaves the house. Main Street America, citing The Trade Desk, reports that nearly 2 in 5 shoppers will have researched their purchases before Thanksgiving and Small Business Saturday, and 38 percent will make their key purchases during that window.

Add the part that does not feel like growth. More than half of the projected spending increase comes from higher prices, not more units sold (Main Street America, 2026). A shop that does nothing differently this year is likely to see flat or slipping volume with a bigger number on the register.

You are now being found by machines as well as people

The second number worth writing down: 24 percent of online shoppers say they will start their holiday shopping on a gen AI platform such as ChatGPT, Claude or Gemini, up from 17 percent last October (Bain, 2026). Bain adds that always-on, AI-enabled comparison makes price gaps easier to spot than ever, so shops outside a reasonable price band drop out of the consideration set before service or loyalty gets a vote.

You might be thinking that this is a retail problem, and you sell services or custom work. Think again about who your holiday customer is. They are the person booking a kitchen refresh before relatives arrive, ordering a custom gift, or hiring someone to get the heat working before the first cold week. They are asking the same tools the same questions.

What those tools can find is what you have published. Hours, services, prices or price ranges, service area, how to book. If the answer is not on your site and your Google profile, the answer is someone else’s.

Start early, because the algorithms need time

Main Street America, relaying Meta’s own guidance, notes that most AI and internet algorithms need time to learn. Content posted for the first time the week of Black Friday is competing against accounts that have been building an audience since October.

The expected demand is concentrated, too. Bain’s survey finds more than 90 percent of shoppers plan to shop Black Friday, Cyber Monday or another major sales event. And 66 percent of small businesses say the holidays drive their overall financial health, according to American Express data cited by Main Street America. For many shops, these few weeks decide the year.

This is where the numbers turn into a plan. A post-by-post approach does not survive a December schedule. A system does:

A site that answers the question. One page with your services, hours, service area and a way to book or call, accurate to the minute.
A listing that agrees with the site. Your Google profile hours and contact details should match, including holiday hours.
Automated replies and booking. An inquiry on a Sunday night should get an answer before you wake up, not after.
Social that posts itself. Three platforms, scheduled through the end of the year, so the work happens once.

What this costs, and when it is not worth it

Be honest about the math. If you take no seasonal work and your calendar is full through January, you do not need a holiday push, and you should not buy one. Fix the website for the long game and leave it there.

If the holidays drive a real share of your revenue, the economics are lopsided. A scheduled content run, an accurate listing and an automated reply flow cost a fraction of one lost job, and they run through the same 27 days when you have no time to do them by hand. This is the work we build at The Trade Script: the site, the listings and the posting running before the rush, so your attention goes to the customers in front of you.

Lead with the shop, not just the tech

Matt Wagner, Chief Innovation Officer at Main Street America, ends his holiday outlook with advice that applies whether you sell cabinets or consultations:

“Leverage the technology, but lead with your story and center the place.” — Matt Wagner, Ph.D., Chief Innovation Officer, Main Street America (2026)

The tools get you found. The story, the craft and the face behind the counter are why they choose you once they arrive.

Do this week: open your own website on your phone and ask the question a holiday customer would ask. Can you find the hours, the services and a way to book in under ten seconds? If not, that is your first November job, and it is cheaper to fix in October.

Sources

2026 Holiday Shopping Outlook, Bain & Company, September 2026
Main Spotlight: Preparing for a Unique Holiday Shopping Season in 2026, Main Street America, September 2026