Forty percent of wine club members cancel within their first year. But the top-performing wineries are pushing retention from an industry average of 60% all the way up to 85%.
The difference isn't wine quality. It's systems, psychology, and how members feel between shipments.
That was the central premise of one of the most tactical sessions at the 2026 Wine Sales Symposium, where Rammy Jaboron (Chief of Staff, Drinks) sat down with Meg Barkley (VP of Marketing & Membership, Clif Family Winery) and Maeve (General Manager, Coursey Graves Winery) to unpack what's actually working in wine clubs right now—and what isn't.
The Real Problem: Transactional Relationships
Jaboron framed the challenge sharply. Most wine clubs fail, he argued, because every touchpoint has become transactional. Shipment reminders. Payment receipts. "Last 48 hours to customize." Members aren't getting anything meaningfully different from what they get from Amazon or Netflix—and that's not what they signed up for.
The panelists represented two very different operations: Clif Family's 10,000-case, subscription-based flexible membership model, and Coursey Graves' 3,500-case traditional three-shipment-a-year club. But their diagnosis of the industry's retention problem was strikingly similar.
Two Models, One Underlying Philosophy
Barkley walked through Clif Family's transition from a traditional allocation model to a fully subscription-based "flexible membership"—and shared what surprised her most about how members responded (including a candid admission about which demographic she expected to lose).
Maeve made the case for staying traditional, and detailed the data signals she watches to decide whether her club is ready to evolve. Her one-word answer for what's keeping Coursey Graves' club healthy right now? Consistency.
Where the Retention Battle Is Actually Won
The panelists dug into the specific mechanics that separate high-retention wineries from the rest:
Why the first 90 days determine everything
The onboarding sequences that are working across generations
What "meaningful engagement between shipments" actually looks like in practice
How much flexibility to give members over their own club
The metrics that matter most (and the churn warning signs to watch for)
They also shared candid tactical details—call times, texting strategies, handwritten note practices, surprise-and-delight programs, and skip-mitigation flows—that attendees were furiously taking notes on.
Watch the Full Session
The full session includes each panelist's specific playbooks, the data behind their decisions, live examples from their programs, and an audience Q&A that got into scheduling, staffing, and the subscription-versus-traditional decision in real depth.
🎥 Access this session, along with all 14 recorded Wine Sales Symposium presentations NOW!