Why the phone matters most in November and December
Every winery sends holiday emails, and every customer's inbox fills up with them. Open rates fall just as the stakes rise. A phone call cuts through that noise. Your customer hears a voice from a brand they already love, gets a personal recommendation, and can place an order — gift shipments included — in a few minutes.
The holidays also bring more complex orders: multiple addresses, gift notes, magnums, verticals and special packaging. Those are exactly the orders people abandon online and happily complete with a person who can sort out the details for them.
Weeks 1–2: Plan the offer and the list (late October)
- Set a revenue goal first. It determines how big the list needs to be and how many calls you'll need to make.
- Keep the offer simple: five or six wines at most, a clear holiday incentive, and one or two gift-ready options such as a curated three-pack.
- Segment the list: wine club members, qualified non-club buyers who've ordered in the last two years, and lapsed customers. Each group gets a slightly different conversation.
- Clean the data. Update phone numbers, remove duplicates and flag anyone who has asked not to be called.
- Check your carriers' holiday cutoff dates and work backwards. The cutoff is the deadline your whole calendar hangs on.
Week 3: Warm up with email (early November)
Send a storytelling email before you lead with an offer: the vintage, the winemaker's holiday table, the wine you open every year. Then follow it with an offer email. The phone campaign should start within a day or two of the offer email so the message is fresh when your team calls.
Email plus a phone call is the combination that works. The email tells the story; the call answers the questions and takes the order.
Weeks 4–6: Call, follow up, repeat (mid-November to early December)
- Call your highest-value customers first, while they are still planning their holidays.
- Leave a short, friendly voicemail and follow it with an email or text the same day, so customers can reply when it suits them.
- Track the basics every day: calls made, contacts reached, orders and average order value. If one segment isn't responding, adjust the offer or the script, not just the volume.
- Ask every buyer about gifts. 'Is there anyone on your list who'd love this?' is the easiest add-on question of the year.
As a guide, an experienced agent can make up to 300 dials a day, and most of our campaigns run two to three weeks. That gives you a realistic idea of how many people your team can reach before the shipping cutoff.
Week 7: Last call before the cutoff
In the final days before your shipping deadline, call back everyone who said 'maybe' or asked you to follow up. Remind them of the cutoff date. Urgency is real at this time of year, and customers appreciate a reminder that saves them from a last-minute gift scramble.
After the holidays: don't waste what you learned
Every conversation creates customer insight: favorite wines, gift recipients, preferences, complaints and upcoming visits. Make sure it goes back into your customer database (CRM). January is quiet, and those notes become the start of your first campaign of the new year.