How to Build Better Wine Club Retention in Between Shipments
The tasting room is winery gold. Always has been, always will be.
There's nothing quite like welcoming guests onto the property, sharing your story over a glass of wine, and creating the kind of hospitality that turns visitors into lifelong members.
But what happens after they leave?
Maybe they visit once a quarter, maybe it's once a year, or maybe they're across the country and may never make it back. Like it or not, the vast majority of your relationship with a wine club member happens somewhere other than the tasting room.
I’ve seen endless "we miss you" campaigns or heavy discounting emails to drive another purchase. Neither creates the kind of experience that keeps members engaged for years.
The wineries with the strongest retention understand that some of the most important customer moments happen between shipments. Every email, every text message, every shipment announcement, every harvest update, and every personalized recommendation is another opportunity to remind members why they joined in the first place.
I recently sat down with Renée Lee, Founder of Loop & Ladder Digital, to talk about how wineries can create those moments through thoughtful lifecycle marketing. From onboarding new members to rethinking the pre-shipment email, Renée shared practical ideas that any winery can use to build stronger, longer-lasting member relationships.
The First 60 Days Set the Tone for the Entire Membership
"We spend so much time talking about getting people to join. We don't spend enough time talking about what happens after they join.”
— Renée Lee, Founder, Loop & Ladder Digital
A new member has made a commitment to your winery, but they haven't yet experienced what it actually means to be part of the club. Instead of immediately trying to sell another bottle or promote the next event, use those first few weeks to reinforce their decision and make them excited about everything that's ahead.
Start your welcome flow immediately
Renée recommends building a structured welcome journey of around five emails. Use that time to introduce your winery's story, explain membership benefits, set expectations for upcoming shipments, and give members a reason to feel confident about what's ahead.
Don't wait days or weeks to continue the conversation. The tasting room experience may be over, but the membership experience is just beginning. Reinforce their decision while the excitement is still fresh, making every new member feel just as welcomed online as they did in person.
Resist the urge to sell again
The first 60 days shouldn't feel like another marketing campaign. Once members understand the value of belonging, personalized recommendations, exclusive offers, and upsells become much more effective.
Use the first month to educate, tell your story, and reinforce the benefits of membership before asking for another purchase. The short-term revenue from an early upsell is rarely worth sacrificing the long-term value of a loyal member.
Create phases of communication
The 5-email welcome flow may be complete, but communication should evolve as the relationship matures. Early on, focus on onboarding and education. Later, shift toward exclusive content, harvest updates, founder messages, loyalty rewards, and other experiences that make long-time members feel recognized.
The goal is to build a stream of communication that recognizes what a member needs in week one looks very different from what they'll value five years into the relationship.
Every Shipment Should Feel Experiential, Not Transactional
Once you've established the relationship during onboarding, it’s time to deliver on the promises you made. The first major opportunity comes before the first shipment ever leaves your winery.
Renée and I both like to geek out over email strategy, and after reviewing hundreds of winery email programs, we've noticed the same pattern. Too often, the pre-shipment email is treated like an operational necessity, a checkbox email notifying members their card is about to be charged and their wine is about to ship.
Renée sees it completely differently. "The pre-shipment email is the most underused, highest-intent moment in the entire membership. It shouldn't feel like a charge warning. It should feel like a reveal and an invitation."
You've invested so much into creating an incredible tasting room experience. Your staff welcomed the guest, shared your story, converted them into a member, and your onboarding emails reinforced that decision.
Don't let the pre-shipment email become the transactional moment that breaks the bottle.
A great pre-shipment experience should make it easy for members to:
Customize their upcoming shipment
Add additional bottles or limited releases
Receive personalized recommendations based on previous purchases
Update payment or shipping information before processing
When done well, everyone wins. Members feel more in control of their membership, wineries reduce failed payments and support requests, and average order values naturally increase through thoughtful personalization rather than constant upselling.
Every interaction should feel like the customer is back in the tasting room talking with your staff, every shipment is another opportunity to remind members why they joined your club in the first place.
Loyalty is Built Between Shipments
The shipment is the biggest moment in a wine club membership. Members have been anticipating it for weeks. They open the box, taste the wines, and experience the product you've worked so hard to create.
But no relationship is built on four moments a year. The shipment is one milestone in a much larger relationship. Everything in between is where loyalty is earned and churn is avoided.
Renée recommends using the months between shipments to continually remind members why they joined in the first place by helping them feel connected to the people, place, and story behind every bottle.
None of those emails should exist with the main goal of selling another bottle, they exist to strengthen the relationship. I’ve talked at length in the past about how a smaller membership that lasts 3 years is more valuable than a larger one that cancels in 6 months.
Renée and I discussed something that might get you in trouble with email marketers: every email doesn't need to generate revenue. Sometimes the goal is simply to remind members that they're part of something bigger than a recurring shipment.
The shipment alone isn't what keeps them coming back, the connection does.
The wineries with the highest retention don't simply deliver great wine every quarter. They consistently remind members why joining the club was worth it, creating dozens of small moments throughout the year that make membership feel personal, exclusive, and connected.
Three Ways to Prevent Churn Before It Happens
By the time a member clicks "Cancel Membership," the relationship has often been weakening for months. Instead of waiting until someone leaves, Renée recommends looking for the warning signs much earlier.
Monitor engagement, not just cancellations
Pay attention to members who stop clicking emails, skip shipments, stop customizing orders, or purchase less frequently between shipments.
Build simple automations to re-engage these members, or create internal alerts for your team to reach out personally. A quick check-in before cancellation is almost always more effective than a discount after they've already left.
Reach out before they're gone
A skipped shipment or several months of inactivity doesn't always mean a member wants to cancel, an active membership continues to extend LTV.
Ask for feedback, recommend wines based on previous purchases, or remind members about benefits they haven't taken advantage of yet.
Learn from every cancellation
Not every member will stay forever, and that's okay. Instead of immediately sending a discount, look for patterns in why members leave, identify gaps in your communication, and refine your lifecycle strategy so future members have a better experience.
Tasting Rooms Will Always Be the Heart of a Winery
The winery experience shouldn’t end when a customer drives away. Every welcome email, shipment announcement, harvest update, and personalized recommendation continue telling their story and reminding members why they joined in the first place.
Technology can automate emails, but it can't automate hospitality. That's still up to us.