Holiday sales begin before the holiday
For retailers, the most important day of a holiday promotion is not the holiday itself.
Stephen Gold, founder of Gold Standard Solutions, said retailers can lose sales by waiting until the final days before an event to launch a promotion. The better approach begins with understanding when customers are likely to shop, preparing the campaign weeks in advance, and giving those customers a reason to return after the holiday has passed.
That preparation becomes especially important in the fourth quarter, when Halloween, Green Wednesday, Thanksgiving, and the December holidays create several opportunities within a relatively short period.
“Preparation is key when it comes to holiday sales because they can really make you,” Gold told Greenway.
“The ability to have the foresight to do that, not everyone has.”
Find the real shopping window
The date printed on the calendar does not necessarily reveal when a holiday campaign should reach consumers.
Halloween falls on a Saturday in 2026, but following Gold’s advice, retailers should not assume Saturday will produce the strongest opportunity.
Consumers attending parties, traveling, or taking children trick-or-treating may purchase products earlier in the week.
“The reality is, the majority of people are shopping on Tuesday,” Gold said. “They’re buying before the weekend. I’m going to get my bud, I’m going to get my edibles. I may be having a party, I may be going to a party.”
For a retailer, that means a promotion built only for Saturday could arrive too late and may fail to drive traffic.
Gold recommended preparing promotional offers and graphics, training employees, organizing the promotion internally, and scheduling email outreach well in advance of a holiday.
Holidays often mean travel, gatherings, or time away from our normal routines, creating a stock-up period several days earlier. Retailers should identify that period rather than assume the holiday itself or the weekends will generate traffic.
Gold said businesses should begin with their own sales and customer data. Gold said analytics tools such as Alpine IQ and Dutchie can be resources that help operators better understand their customers’ demographics.
That information can challenge outdated assumptions about the typical dispensary customer.
“The average consumer in a dispensary is a lot older (than we think),” Gold stated. “It might be someone in their late 30s, 40s, 50s, or 60s. That consumer has a lot more money to spend than someone who is just out of college.”
Rather than building every campaign around a young, single consumer, retailers may need to speak to parents, professionals, and established customers balancing work, travel, and family plans.
Gold said those consumers can represent valuable repeat customers because they may have more purchasing power and larger baskets.
Plan Green Wednesday before November
Gold described Green Wednesday, the day before Thanksgiving, as one of the industry’s most important sales occasions. He said some Gold Standard clients were already developing their November plans months ahead of the event.
That planning can turn Green Wednesday from a one-day discount into a coordinated monthlong campaign involving featured brands, co-marketing agreements, timed offers, email, text messaging, website content, and in-store execution.
“Green Wednesday turns into a whole month where we’re featuring certain brands, we’re co-branding,” Gold said. “I think that’s one way that you can really win as a dispensary owner. How do I assume the least amount of risk by asking brands to be involved, to do co-marketing efforts, and to understand what levers the brands can pull for you?”
Early brand participation gives retailers time to determine which partners will support the campaign, coordinate co-marketing efforts, prepare compliant creative, and organize the timing of different promotions.
Gold also cautioned against treating website preparation as a last-minute task.
A retailer that waits until November to create a Green Wednesday landing page may have difficulty gaining search visibility.
“If you’re planning for the day of and you’re going to advertise it the day before, you’re going to lose because someone else in your market is way ahead of the ballgame.”
During the conversation, the importance of maintaining holiday landing pages year over year was also discussed. Rather than deleting seasonal pages after the holiday, retailers can update existing pages with new offers, graphics, and participating brands while preserving the search history those pages have built.
The same approach applies to mobile optimization. Consumers searching for nearby retailers, menus, and promotions are often doing so from their phones, making a mobile-friendly experience a critical part of holiday preparation.
In saturated markets, a discount alone may not distinguish one retailer from another. Businesses often carry similar brands, sell comparable products, and promote many of the same price reductions.
“Everyone’s got the same product,” Gold said. “Everyone’s advertising deals. How are my deals or my perceived values at my store going to make a difference versus the other person that’s going to have the same things going on?”
Gold said the answer includes converting promotional traffic into repeat business. A retailer that spends money to attract a customer, provides a discount, and never captures customer information may miss the opportunity to build a long-term relationship.
Loyalty enrollment should be simple, appropriately timed, and supported by a meaningful incentive. Gold said his experience at Weedmaps showed that promotions below 20% generally failed to move the needle with consumers.
For loyalty enrollment specifically, Gold suggested that offering a meaningful future discount can make customers more willing to provide their information.
“The order’s in, the money might be in the door, and we’re just waiting for the order to come out,” Gold explained. “Hey, by the way, do you want 20% or 25% off your next purchase? Can I get your email address or can I get your phone number?”
The timing of that interaction matters. The period when a customer is waiting for their order may provide an opportunity for employees to introduce loyalty programs without interrupting the transaction.
Giveaways can provide another point of differentiation. Tickets, gift cards, experiences, or locally relevant prizes may be more memorable than another discount while giving employees a straightforward reason to ask customers to enroll.
Gold suggested evaluating those programs by customer acquisition cost. He offered the example of spending $350 on two tickets and asking whether a retailer could generate 350 loyalty signups. If successful, that would represent approximately a $1 acquisition cost per new contact.
List size is not engagement
Collecting contact information is only the beginning. Gold warned that a large email list can provide a false sense of reach when recipients no longer engage with messages.
A retailer sending weekly promotions to 15,000 addresses with a 10% open rate may be reaching only a fraction of that audience. Gold emphasized that list health and engagement matter more than simply increasing the number of contacts.
“Cleaning your list hygiene is super important,” Gold said. “That’s not a month-before thing. That’s like a six-month-before thing where you’re really training your list to grow in the right direction. It’s not about how many emails you have.”
Gold also cautioned retailers against immediately adding purchased lists to their regular email distribution. Instead, he said those contacts should be approached strategically to determine who is likely to engage.
For retailers preparing for the holiday season, Gold’s advice ultimately extends beyond choosing a discount.
The campaign should begin with store-level data, account for when customers will actually shop, reach them before they make their purchasing decisions, and continue after the promotion through a deliberate loyalty strategy.
A holiday can create traffic.
Whether that traffic becomes durable revenue depends on the work completed before the date arrives.
