Time for a Review?
If your winery’s wine club sign-ups are flatlining, especially at the cellar door, it’s time to ask a tough question: What’s actually holding us back? The answer usually falls into one of three buckets — tech, strategy, or staff.
Let’s break each one down.
1. Your Tech Stack: Are the Basics Covered?
Let’s start with the obvious: your systems. If your tech makes it hard to sign someone up on the spot, automate payments, or allow members to manage their subscriptions online — that’s a problem.
Here’s what “baseline functional” tech should look like:
Ability to add a new subscriber to your system upon conversion
Payment processing should be automated
Members should be able to swap, or update their packs without emailing you.
Emails and/or SMS reminders should be part of the flow (not an afterthought).
If any of these are missing, that’s your starting point. No amount of strategy or salesmanship can fix a broken backend.
2. Your Strategy: Are You Creating An Experience & FOMO?
Tech gets you in the game, but strategy wins it. A common wine club mistake? Waiting for someone to “ask” to join. If you’re not actively prompting the conversation, you’re losing potential subscribers.
Try this instead:
As soon as someone walks into your cellar door, your staff should ask: “Are you a wine club member?” — that question alone triggers curiosity.
Show them value: exclusive tastings, members-only events, discounts, or surprise perks.
Use smart upselling: if they’re buying four bottles, suggest two more to unlock a six-pack discount — and tie that directly into the wine club offer.
Offer flexible plans: let members pick their wines, or choose a 3-, 6-, or 12-bottle tier.
Promote seasonal drops and limited-edition packs to keep the club feeling exclusive and dynamic.
Don’t bury the offer — make it front and centre in your in-person and digital touchpoints.
Your goal? Make the wine club feel like the logical next step, not a pushy pitch.
3. Your People: Are They Bought In?
You can have rock-solid tech and a smart strategy — but if your team isn’t pushing the club, it all breaks down. Sales training matters, but mindset matters more.
Ask yourself:
Do your staff believe in the club and its value?
Are they bringing it up naturally in conversation — not as an afterthought?
Are they incentivized to sign people up?
Do they understand how the club benefits the winery long-term?
Are you celebrating team wins when someone hits a sign-up goal?
Do they feel confident explaining the offer — on the spot?
- Do you have a dedicated person managing your members?
The best-performing wineries build a culture where everyone owns the goal of turning tasters into subscribers. If the team’s not all-in, neither are your results.
Wineries that have a dedicated Wine Club Manager/Concierge also see an increase in conversion due to the way they approach communication and selling – in a more relationship style rather than transactional. We’ll write a full blog post on this method of selling vs a pure transactional method in collaboration with one of our partners that really understands these differences.
Time to Diagnose
If your wine club growth has stalled, you’re not alone. In tougher economic times, conversions are harder to come by. But before throwing more money at marketing, switching tools, or launching another promotion, pause and ask:
Is my tech helping or hindering?
Is my strategy proactive and value-driven?
Is my team aligned and accountable?
Pinpoint the weak link, fix it, and momentum will return—not just in more sign-ups, but in better members who stick around.
In most cases, it’s that last question that trips wineries up.
We’re seeing the most success from wineries where staff are truly all-in—focused on delivering an exceptional cellar door experience, aligned around club conversion goals, and supported by a dedicated club manager offering concierge-style service. That’s what’s driving both conversions and long-term retention. (More on this in an upcoming post.)
