Tips for a Smooth and Successful Holiday Selling Season

Retailers are gearing up for the year’s biggest months. Here are eight essential rules for reducing headaches and increasing profits

ACME Fine Wines. Photo by Emma K. Morris.

Despite lingering pandemic concerns, persistent staff shortages, and supply chain woes, retailers are looking forward to a holiday season that could almost feel normal—at least compared to last year. 

We spoke with retailers across the country to get their top tips for ensuring the season goes as smoothly—and profitably—as possible. 

Get a head start with your corporate clients

When it comes to assisting clients with their gift lists, there’s no such thing as too early. “This year, we were very proactive,” says Jeffrey Wolfe, owner of Wolfe’s Wine Shoppe in Coral Gables, Florida. “For the first time, I mailed an actual letter to former, current, and potential clients focused on tips for stress-free holiday personal and corporate gift-giving. I laid out the required timing, the info I need, and what I can do in terms of selection, gift notes, and delivery.”

“We contact our clients in October letting them know that gifting early is the new late,” explains Karen Williams, proprietor of ACME Fine Wines in Napa Valley. She also lets them know that they’ll need to use the ACME company spreadsheet. “We have a proprietary format that speeds up the gifting process so that unnecessary, precious, unavailable time isn’t spent deciphering or reconfiguring hundreds of business and personal spreadsheets.” Put in place several years ago, “it has allowed us a streamlined holiday bliss of our own.”

And don’t forget the virtual get-together. “People are still working remotely and companies are finding unique ways to keep the team together,” says Sunshine Foss, the owner of Brooklyn’s Happy Cork. “You definitely want to take advantage of this.” Check in with existing clients to see if there’s interest in offering a virtual tasting to their team or their own clients. This can be as simple as conducting a Zoom tasting focused on the wine your client is already gifting, or as complex as working with a food purveyor to do a combined tasting. While it may be too late to schedule something for the holidays, you can also lay the groundwork for events in the new year.

Consider supply chain issues in your buying decisions

Supply chain disruptions have made stocking up on core items a challenge for over a year—and the holidays will only put more pressure on an already stressed pipeline. It will be particularly problematic for key categories like Champagne. “We are locking in Champagne buys much earlier than we might otherwise,” explains Jill Bernheimer, owner of Domaine LA in Los Angeles. She ordered the Champagne for her December wine club back in September. “I can’t risk not being able to get product which is exactly what might happen if I hesitate even a few days.” (Are you already feeling behind?)

This year it will be critical to have a list of backup options—the more, the better. “This year, we are moving a bit beyond the well known names of Champagne and trying to find more delicious sparkling wines from around the world,” says Cara Patricia, cofounder of DECANTsf in San Francisco. “We are bringing in a greater variety of SKUs from the smaller growers whom we’ve built relationships with over the years.” Their selection includes crémants from the Loire Valley and Burgundy, Franciacorta from Italy, and for the adventurous, bubbles from the Canary Islands.

Credits from left to right: Wolfe’s Wine Shoppe in Florida, DECANTsf in San Francisco, and Center Wine & Spirits in Connecticut.

Buy deep (and familiar) to keep margins healthy

‘Tis the season to buy deeper on key items. Analyze past sales history and “for fast-moving wine, if you don’t always buy the deep deals, Q4 is the time to do it,” says JT Robertson, general manager at Le Du Wines in Manhattan. “There is often an opportunity to save five to 10 percent on the bottle cost at larger quantities. This might not make sense during slower quarters, but in Q4, a dollar here, a dollar there adds up very quickly.”

“Consider strategically overbuying,” suggests Erin Bender, general manager at Irving Bottle in Brooklyn. “We’ll stock up on higher-end items to take advantage of seasonal deals, knowing we’ll sell some during the holidays and the rest throughout the next year.” This does tie up cash, but if the discounts are deep enough, the positive margin impact can be worth it.

This is also the time to focus on the classics. “We always increase our collection of cru Beaujolais, Napa Valley Cabernet Sauvignon, Bordeaux, Barolo, and Brunello beginning in October,” says DECANTsf’s Patricia. “The meals prepared in the fall and winter just seem to love those wines.” Customers gravitate to these familiar regions as well, which makes life easy. Once the holidays are over, and customers and shop staff have more time, retailers can return to hand-selling their store’s quirkier wines.

Let your displays do the talkingand the selling

Set up your displays so they make it easy for your customer to grab and go. Wolfe’s Wine Shoppe offers grape variety-focused six-packs as well as an “everything you need for the holidays” case that typically includes a mix of crowd-pleasing reds, whites, and of course, bubbles. Marissa Ocasio, education director at Center Wine & Spirits in Glastonbury, Connecticut, suggests displaying cocktail ingredients together; for example, group a popular gin, Campari, and vermouth together for shoppers to make Negronis, and consider including accessories such as large ice cube trays. At my shop, Copake Wine Works in upstate New York, we keep a table full of small-format bottles available as stocking stuffers.

David Ucci, head of sales at Vino di Vino in the Boston area, recommends a “good, better, best” approach, showcasing wines from three different price points within a category. “This could be variety, region, country of origin, or producer,” he explains. “Then I can easily point to something that’s understandable for the customer.” This allows the customer to choose the price point that’s right for them, which may be higher than you think. Remember, this is the time of year to “sell fearlessly,” Ucci adds. “The last thing you want to do is undersell your customer and not give them the option to give the perfect gift that they want to give.”

Don’t forget the go-to gift card

Gift cards are a holiday staple, so make sure you offer them in some form. While virtual certificates that can be used both online or in-store are the holy grail, old-school paper cards tracked on a spreadsheet can also work. No matter what format you use, be sure to clearly communicate the expiration date. “Make sure you train your staff on how to sell them, how to redeem them, and where you store them—before the season kicks into gear,” stresses Irving Bottle’s Bender.

Photo courtesy of Vinodivino.

Be strategic about gift wrapping

Gift wrapping options can range from intricate and involved, to simple and efficient, and retailers should seriously consider the space and staff required for prep work and storage before developing their strategy. Branded elements add a special touch but require longer lead times to order and involve higher costs. “We use gift bags instead of traditional wrapping to keep things moving,” suggests Center Wine & Spirits’ Ocasio, “and we pre-curl the ribbon.” 

TJ Douglas, who owns Urban Grape in Boston with his wife Hadley, invests in a more elaborate gifting set up and then brings in additional staff to manage it. “We make sure that only a few people are doing gift wrapping and that they are trained the same way so that every single package comes out looking beautiful,” he shares. 

For shops that have the necessary space, Allegra Angelo at Vinya Wines in Miami suggests “making a boxing station that is grand and over-the-top. Make it an experience. Have a pitcher of homemade drinks, one alcoholic and one non-alcoholic. For example, we’re serving a twist on Coquito, a creamy, rum-spiked Puerto Rican drink.” This sort of display can highlight your gift wrapping offerings and entertain your customers while they wait.

Be totally honest about shipping deadlines

If your shop does any shipping and you haven’t already ordered your materials, stop reading this article and go order them now. 

Next: It’s critical to know the most current cut-off dates for all common carriers. UPS and FedEx aren’t guaranteeing arrival dates for many of their services, so retailers shouldn’t either. “It is always better to be upfront with a customer about limitations and possible delays,” says Le Du’s Robertson. “Even if it means you lose the sale because you’re telling someone the truth about what could happen, it’s always better than failing their request because of reasons beyond your control.”  

While ground shipping is more economical, be sure to offer expedited shipping for reasons of weather and timing. “We let guests know that if they’re worried about the extra bucks it costs for expedited shipping, we recommend that they call up a wine shop more local to their recipient and place an order with them,” says DECANTsf’s Patricia. “We’re always happy to recommend shops that carry comparable wines.”

Make sure all staff members stay happy and healthy

Even for shops that have the relative luxury of being fully staffed, it’s still going to be a wild ride. “The temptation is to go full throttle from morning until night,” says Ucci. “But it’s really important to build in down time for your teams so that everybody can maintain a high level of reserves. They need to have something at the end, because that’s when it’s the hardest.”

At Copake Wine Works we kick off the season with an all-hands-on-deck training session to review store procedure and holiday-specific processes—as well as eat pastries and drink the first of many coffees. At ACME Fine Wines, “We’ll have pizza and Champagne gifting parties if we go late into the after-hours work day,” says Williams, “It keeps morale high.” Whatever you’re pouring, make sure to include everyone—salespeople, cashiers, delivery teams, stock people, and gift wrappers—because nothing makes the holiday season go more smoothly than a well-trained, and well-fed, team.


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Christy Frank is a partner at Copake Wine Works, a shop in the Hudson Valley of New York. She is an advanced sommelier with the Court of Master Sommeliers and holds the WSET Diploma in Wines.

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