1. Flexibility Is No Longer a Perk. It’s Expected.

Consumers expect control.

Pause. Skip. Swap. Adjust frequency. Update preferences without calling or emailing.

In most industries, this is standard. When wine clubs feel rigid — fixed shipments, limited customization, clunky portals — friction increases. And friction leads to cancellations.

This isn’t about flaky members.
It’s about modern loyalty needing to feel adaptable.

Wineries embracing flexible billing, customizable shipments, and self-service tools are discovering something powerful: flexibility doesn’t weaken commitment, it strengthens it. When members feel in control, they stay longer.

2. Relevance Drives Retention

Consumers are flooded with options. What stands out now is relevance.

One-size-fits-all messaging and generic shipments don’t hold attention the way they once did. Today, members are quietly asking:

• Does this reflect my taste?
• Does this brand know me?
• Does this feel curated or automated?

When communication feels tailored, engagement rises. And engagement fuels retention.

Relevance starts with data, but it’s brought to life through thoughtful storytelling.

3. Connection Outperforms Convenience

Convenience built the subscription economy.
Connection sustains it.

The brands thriving today offer more than product delivery. They build emotional ecosystems through:

• Insider access
• Ongoing education
• Community-driven experiences
• A sense of identity and belonging

Wine has a natural advantage here, it’s already rooted in story, place, and shared experience. The opportunity is to lean into that strength intentionally.

Why Wine Has the Upper Hand

Unlike many subscription categories, wine is inherently emotional.

It’s not just a product. It’s:

• A dinner party.
• An anniversary.
• A Friday night ritual.
• A vineyard memory.
• A winemaker’s story.

Wine is tied to place, people, seasonality, and shared experience.

That emotional dimension is something streaming services and meal kits have to manufacture. Wineries already have it, they simply need to activate it more intentionally.

When clubs struggle, it’s rarely because members “don’t like wine anymore.”

It’s because:

• The story stopped.
• The communication slowed.
• The experience felt repetitive.
• The relationship plateaued.

In other words, the model stayed static while consumer expectations evolved.

Passive Members vs. Emotional Advocates

There’s a meaningful difference between someone who lets shipments auto-process and someone who tells friends about you, brings guests to visit, posts photos from your events and pens every email because they genuinely care what you have to say.

Passive members participate quietly. They receive the wine. They enjoy it. They may even like your brand. But their engagement is limited. There is no deeper attachment. Advocates are different. Advocates talk about you. They recommend you. They defend you. They look forward to your releases and feel proud to pour your wine at their table.

Passive members tolerate you.
Advocates choose you.

Passive members stay until they review their credit card statement and decide whether it still makes sense.
Advocates stay because your brand feels aligned with who they are.  One group is driven by convenience, the other is driven by connection.

The goal of a modern club is not simply retention percentages or shipment counts. It is building a sense of belonging that turns customers into community members and members into ambassadors.

Belonging > Discounts

There has been a subtle but powerful psychological shift happening in loyalty programs across every industry, and wine is no exception.

Discounts reward transactions.
Belonging rewards identity.

A discount says, “Here is a financial incentive to stay.” It is practical and sometimes effective, but it is rarely emotional. It does not create attachment. It does not create pride. It simply reduces friction in the moment.

Belonging works differently. Belonging says, “You are part of something.” It invites someone into the story, into the process, into the philosophy behind the bottle.

When a member feels like an insider, everything changes. When they understand why a certain block was harvested earlier this year, why the winemaker adjusted the blend, or how a vineyard decision shaped the final wine, they feel invested in more than a shipment. They feel connected to the outcome.

That connection transforms the experience from consumption to participation.

Education becomes empowerment in this environment. Instead of simply receiving wine, members gain language, confidence, and context. They learn how to talk about what they love. They begin to recognize structure, acidity, texture, and balance. They understand why a wine pairs beautifully with a particular dish. That knowledge builds confidence, and confidence builds pride.

When members feel smart about what they are drinking, they naturally want to share it. They bring the wine to dinner parties and tell the story behind it. They recommend the club to friends because it reflects well on them. In sharing, they become advocates.

The most resilient wine clubs in 2026 will not win by offering the deepest discount or the most aggressive promotion. They will win by creating connection, by fostering community, and by helping members feel like they belong to something meaningful.

Price can attract attention.
Connection creates loyalty.

3 Signs Your Club Is Transactional (Not Relational)

1. You only communicate around shipments.
   If members only hear from you when billing runs, your club feels like an invoice.
2. All members receive identical messaging.
   No segmentation. No behavioral targeting. No recognition of tenure.
3. You don’t track engagement — only revenue.
   If you measure shipments but not opens, event attendance, or visit frequency, you’re flying blind.

None of these are permanent problems. They’re solvable.

One Personalization Lever to Activate Immediately

Start with preference tagging.

In your CRM, begin tagging members by:

• Favorite varietal
• Red vs. white preference
• Visit history
• Event attendance
• Purchase behavior (case buyers vs. explorers)

Then do one simple thing: Send one segmented email this month based on those tags.

For example:

• Rhône lovers receive a blending story.
• Sparkling fans receive a food-pairing guide.
• Long-term members receive a loyalty spotlight.

Small changes create noticeable impact and when members notice, churn decreases.