Is Your Wine Club as Healthy as It Looks? 7 Signs to Watch

A full pickup party, a successful club run, or a steady stream of new signups can make a wine club look healthy.

But none of those numbers tells the whole story.

Wine club health is less about one standout metric and more about what members are doing over time. Are they buying between releases? Are new members replacing the ones who leave? Are long-term members continuing to engage? Is purchasing behavior holding steady, growing, or quietly declining?

The strongest wine clubs look beyond shipment revenue and pay attention to the patterns underneath it.

Here are seven signs worth watching.

1. Members buy outside their scheduled club shipments

A club shipment tells you a member is still enrolled. Purchases outside that shipment can tell you something more.

When members return to the tasting room, place ecommerce orders, attend events, or make additional purchases between releases, the relationship extends beyond the club commitment itself.

Look at how many members purchase outside scheduled shipments and how often they do it.

If that activity begins declining, it does not automatically mean members are preparing to cancel. But it may be worth asking whether there are enough reasons for members to engage with the winery between releases.

2. Purchase frequency and recency remain strong

Two useful questions to ask about your members are:

• How often are they purchasing?

• How recently have they purchased?

A member who purchased last week and has ordered several times this year has a very different relationship with the winery than a member whose only recent transactions are automatic club shipments.

Neither behavior guarantees what that member will do next. But looking at frequency and recency across your membership can reveal changes that a total revenue number may hide.

Pay particular attention to shifts over time. Is the average member purchasing more frequently, less frequently, or about the same as a year ago?

3. Members are actually using their benefits

Discounts, complimentary tastings, member events, early access, shipping offers, exclusive wines: wineries invest a lot in creating reasons to belong.

But are members using them?

Benefit usage can be a useful indicator of whether members are actively participating in the club experience.

It can also expose a different problem. If members rarely use a particular benefit, the answer is not necessarily to add another one. The existing benefit may not be valuable enough, members may not know about it, or accessing it may be too difficult.

Before adding more to the club, understand what members already value.

4. Signups are outpacing cancellations

New member signups are exciting, but they are only half of the growth equation.

If 30 people join the club this month and 28 cancel, the club technically grew. But that tells a very different story than 30 signups and five cancellations.

Track:

• New member signups

• Cancellations

• Net club growth

• Cancellation rate

Looking at these numbers together helps distinguish acquisition from actual club growth.

If signups are strong but membership stays flat, the bigger opportunity may not be finding more new members. It may be understanding why existing members are leaving.

5. Member tenure is holding steady

How long do members stay?

Average or median club tenure gives wineries another way to look at retention beyond monthly cancellation numbers.

It is especially useful when tracked over time. If newer groups of members consistently leave sooner than long-term members did, something may have changed in the member experience, expectations, acquisition strategy, or club structure.

Tenure can also help identify what your longest-standing members have in common. Understanding why someone stays for five or ten years can be just as valuable as understanding why someone cancels after one.

6. Spending and purchasing behavior aren't quietly changing

A member does not have to cancel for their relationship with the winery to change.

They may stop making additional purchases. Their average order value may fall. Their visits may become less frequent. They may shift from several channels to club shipments only.

Individually, these changes may mean very little.

Together, they can show that a member's relationship with the winery is changing.

Instead of looking only at whether someone is an active club member, look at how their behavior today compares with their own past behavior.

7. You're looking at the whole picture

This may be the most important one.

No single metric defines a healthy wine club, and no single behavior tells you that a member is going to leave.

A member who has not visited the tasting room recently may live across the country. Someone who has not placed an ecommerce order may still attend every member event. A longtime member may purchase less frequently but consistently renew year after year.

The useful insights come from combining signals.

Club growth. Tenure. Purchase frequency. Recency. Additional purchases. Engagement. Spending patterns. Cancellations.

Together, they provide a much clearer picture of club health than any one number on its own.

Healthy Clubs Don't Just Grow. They Keep Members Engaged.

It is easy to judge wine club performance by the most visible numbers: how many members joined, how much the latest release generated, or how many people attended the last event.

Those numbers matter.

But a healthy club is also one where members continue to find reasons to buy, visit, engage, and stay.

The first step is knowing where your club stands today.

How healthy is your wine club?

Take the Wine Club Scorecard to see where your club is strong and where there may be opportunities to improve.

Take the Wine Club Scorecard →

Built on vinSUITE’s analytics, Ask Vinny helps teams move from questions to answers to action in seconds.

vinSUITE today announced the launch of Ask Vinny, an AI assistant built directly into the vinSUITE platform to help winery teams ask questions and get immediate answers from their own business data.

Ask Vinny marks a major step forward in how wineries interact with their software. Instead of searching through reports, building dashboards, exporting spreadsheets, or waiting on someone else to pull data, winery teams can now ask a question the way they would ask a colleague and receive an answer based on their own sales, customer, wine club, ecommerce, and tasting room data.

For years, wineries have collected more data than ever, but the ability to use that data has often been limited to whoever knew how to pull the right report. Ask Vinny changes that. Owners, general managers, wine club managers, tasting room leaders, and DTC teams can now ask questions like which club members are most at risk of cancelling, why cancellations increased last month, how a club release compared to last year, which tasting room associates converted the most visitors into members, or which customers have not purchased outside a club shipment in the past year.

Ask Vinny builds on vinSIGHT, vinSUITE’s analytics platform that already helps wineries understand wine club churn risk, customer behavior, lifetime value, RFM segments, sales trends, and revenue opportunities. By combining vinSIGHT’s winery-specific analytics with AI, Ask Vinny gives users a faster and more intuitive way to analyze their operations without needing to build a report first.

“For more than twenty years, winery software has required people to hunt through reports to find answers,” said Jimmy Wu, President of vinSUITE. “AI changes that. Ask Vinny lets anyone on a winery team simply ask a question and immediately understand what is happening in their business. More importantly, it does not stop at insights. When applicable, it identifies the customers behind the numbers and gives teams the information they need to take action right away. We believe this represents the next generation of winery software.”

Unlike general-purpose AI tools, Ask Vinny is built specifically for winery DTC operations and works inside the vinSUITE platform. It draws from a winery’s own vinSUITE data, including sales, orders, customers, wine club activity, ecommerce performance, POS activity, and historical behavior. Every answer is grounded in the winery’s data, not outside assumptions.

Ask Vinny also makes results usable. In addition to plain-language summaries and the numbers behind each answer, users can export detailed result tables when applicable, including customer names, email addresses, and phone numbers. That means a wine club manager can ask for members at risk, a DTC team can identify lapsed buyers, or a tasting room leader can find follow-up opportunities, then use the results for real outreach.

Every Ask Vinny response includes the time period analyzed, the steps taken to generate the answer, and the source data used, helping teams understand and trust the results. The assistant is read-only by design, so asking a question cannot change a record, update an order, or alter customer data.

Ask Vinny also keeps recent questions in context, allowing users to follow a line of thinking without starting over. A winery can ask what happened, ask why it happened, narrow the results, and export the list needed to take action.

Ask Vinny is available now, free, to vinSUITE customers with vinSIGHT user access.

See what your winery can ask at https://hub.vinsuite.com/ask-vinny.

Less Than Two Weeks Until the 2026 Wine Club Symposium: Here's What's Happening on Day 1

The countdown is on. In less than two weeks, winery professionals from across the industry will come together for the 2026 Wine Club Symposium, two mornings dedicated entirely to growing, retaining, and strengthening wine clubs.

Whether you're a winery owner, DTC manager, wine club manager, or tasting room leader, Day 1 is designed to help you understand where the industry is headed and what you can do today to improve your club's performance.

Session 1: State of the Industry: What the Data Says About the Future of Wine Clubs

The symposium opens with an industry outlook from Rob McMillan, EVP & Wine Division Founder at First Citizens Bank, joined by Jimmy Wu, President of vinSUITE.

Together, they'll examine current market trends, changing consumer behavior, and the data shaping winery DTC strategies. Expect practical insights into what's driving successful wine clubs today and where wineries should focus as they plan for 2027.

Session 2: Delivering Loyalty: Insights & Data to Power Your Next Club Release

Your club shipment doesn't end when the order is processed.

In this session, Karin Strykowski of Wineshipping explores how fulfillment, communication, and the delivery experience influence member satisfaction and long-term retention. Learn how wineries can create a smoother club experience from checkout to doorstep while reducing common friction points.

Session 3: Your Next Club Member Is Already on Your List

Finding new club members doesn't always require finding new customers.

Erica Walter of Email Mavens shares strategies for identifying your highest-potential members from the audience you already have. You'll learn practical email marketing techniques that encourage more conversions while making better use of your existing database.

Join Us September 15-16

The Wine Club Symposium brings together industry experts and winery professionals to share real-world strategies you can apply immediately. If growing your wine club is a priority this year, these sessions provide valuable insights you won't want to miss.

Registration is free, and if you can't attend live, you'll still receive access to the session recordings. Register here: https://hub.vinsuite.com/wine-club-symposium-2026.

We look forward to seeing you online September 15-16.

vinSUITE Names Steven Thomas to Lead R&D, Bringing Smarter Tools to Wine Clubs and Tasting Rooms

The Napa-based direct-to-consumer software company adds a senior technology leader to bring practical AI to the platform wineries run on every day.

NAPA, Calif., August 12, 2026 - vinSUITE, the direct-to-consumer software platform for wineries, has named Steven Thomas as Vice President of R&D and AI. Thomas will lead product engineering and own the platform’s push to bring AI into winery DTC software, not as a feature on a slide, but as tools wineries can actually trust and use.

Tasting room traffic still hasn’t bounced back, and keeping club members is only getting harder. For a winery, the software behind the wine club, the tasting room, and the online store is where the customer relationship lives, and it has to do more than record what already happened. vinSUITE has hired Steven Thomas to make that software smarter, and to put AI to work for wineries in ways that are practical.

 “Our customers do not wake up thinking about software. They think about their wines and their members,” said Jimmy Wu, president of vinSUITE. “Our job is to make the tools behind that work quietly and well, and to be careful and honest about how we bring AI into them. Steven has spent his career building technology that people can depend on, and that is the mindset we want leading this work.”

Reinventing vinSUITE’s software starts with the problems wineries face every day: spotting which club members are about to cancel before they do, turning tasting room visits into follow-ups that convert, and giving small teams the kind of insight into their DTC business that usually takes a data analyst.

 “The best technology should make the customer experience feel easier, smarter, and more personal. My focus at vinSUITE is to bring my experience across product innovation, eCommerce, payments, and AI to help wineries strengthen the relationships that keep members coming back, and grow their DTC business with confidence,” said Steven Thomas.

Thomas joins vinSUITE after leading technology as a chief technology officer across FinTech (banking, payments, and eCommerce), industrial IoT, and telecommunications. Across all of it, his focus has held: taking AI and machine learning from concept to dependable, in-production tools. He is a founding partner of the consulting firm The Forge and holds a degree in Computer Science from Western University.

For vinSUITE, the hire signals a continued investment in the platform that hundreds of wineries count on every day. With more than 20 years in the DTC wine business, the company brings together wine club management, eCommerce, point of sale through TabletPOS, and reporting through vinSIGHT on a single platform, and is now building the next layer of intelligence on top of it.

 “Software for wineries has been about recording what happened, last month’s sales, who’s in the club, what’s in inventory,” said Wu. “The next step is software that helps wineries see what’s about to happen and do something about it. That’s where we’re headed, and that’s why Steven’s here.”

Learn more about vinSUITE at [vinsuite.com].

About vinSUITE

vinSUITE is a software platform built for winery direct-to-consumer and wine club operations. It brings wine club management, eCommerce, point of sale through TabletPOS, and analytics together on one platform, helping wineries sell directly to their customers and keep club members longer. With more than 20 years in the DTC wine business, vinSUITE works with wineries of every size. Learn more at [vinsuite.com].

Retention Is the New Growth: Inside the 2026 Wine Club Symposium

You can feel it on a quiet Saturday. The floor is not as busy as it used to be. The people who come in are lovely, but there are fewer of them, and the tasting room is no longer carrying the year the way it once did. Meanwhile the club keeps sending wine, keeps posting revenue, and keeps quietly holding the whole business together.

That shift is why we built this year's Wine Club Symposium around a single idea, and why we moved it up to September. For most wineries, the club has become the most dependable recurring revenue they have, right as it comes under real pressure. Long-time members are aging. Younger members want something different. And growing the club by simply adding names is not the lever it used to be.

For years, the job was growth. Sign more members, and the numbers took care of themselves. That math has quietly flipped. Net club growth has cooled from its peak, while the value of each member you keep has never been higher. The winery that holds onto its members and deepens those relationships is now in a stronger position than the one chasing sign-ups.

Retention is doing the work that growth used to do. The winners are not the ones cutting the most. They are the ones paying the closest attention to the members they already have.

It starts with an honest look at the numbers

To open Day 1, Rob McMillan and Paul Dugoni of Silicon Valley Bank sit down with vinSUITE president Jimmy Wu for a data look at where DTC and the wine club stand today. Rob is the author of SVB's annual State of the Wine Industry Report and one of the most-quoted analysts in the business. The picture is clarifying: the industry has split in two. A few wineries are pulling ahead, most are holding flat, and the gap between them is widening. The difference is not the model. It is the execution. Everything else across the two mornings is a piece of that playbook.

Keeping the members you have

The fastest revenue in your business is the member who does not cancel. Two sessions go straight at that.

In Delivering Loyalty, Karin Strykowski of Wineshipping digs into what actually happens between a release announcement and a package on a doorstep. Loyalty is not built by great wine alone. It is earned at every touchpoint, from the first release email to the last delivery, and Karin brings the data behind club runs that land well from start to finish.

In The Generational Shift in Your Wine Club, Megan Currie of the Wine Club Professional Network gets past the easy generalizations about younger drinkers and into what actually moves people to join a club, stay in it, and tell a friend. Clubs built for one generation are starting to feel their age. Megan turns that into practical club design you can act on.

Finding your next member without spending more

Keeping members matters. So does finding the right new ones without spending more to do it.

In Your Next Club Member Is Already on Your List, Erica Walter of Email Mavens makes a simple case: your next member is already opening your emails and buying your wine. You just have not invited them yet. She shows how to turn the emails you already send into low-cost ways to grow the club, no extra ad spend required.

In Getting Found, Pamela Snyder of DigiVino and Van Potts of Preston-Layne and Partners look at how discovery itself is changing. AI and new search habits are rewriting how people find wineries, and what worked a year ago is already slipping. They cover why share of shelf is becoming share of mind, and how a small team can own its visibility.

Getting the plan approved

You can see what your club needs. The hard part is often the conversation with the people above you. In Managing Up for Wine Club Managers, Liz Mercer of WISE shares how to bring a new idea to your owner or GM and actually move them: how to frame it, how to back it, and how to earn buy-in instead of stalling out. As she puts it, bad news does not age like fine wine. This is the session that turns everything else on the agenda into something you can get done.

Why we host it

We host the Symposium every year for the same reason we built vinSUITE: to help wineries run stronger clubs. It has always been less about vendors talking at wineries and more about wineries learning from one another and from the specialists who work alongside them. The tagline this year is the playbook for a stronger club, and that is the honest goal, two mornings of practical, usable ideas you can take back to your team.

Two mornings. Six sessions. Nine speakers on the work that matters most to your club right now. Tuesday, September 15 and Wednesday, September 16, 2026, 9:00 AM to 12:00 PM PT both days. Free and virtual, and every session is recorded if you cannot make it live.

Save your seat for the Wine Club Symposium 2026.

September 15 & 16, 2026 · Free Virtual Event

The Wine Club Symposium returns for a fourth year, now in September. Over two mornings we bring together specialists from across the wine industry on the work every winery is focused on right now: growing the club and keeping the members you have.

See more details and register here.

Hosted by vinSUITE, the free two-day event brings specialists from across the wine industry together to answer one question: what’s working for wine clubs right now.

vinSUITE, the software platform built for winery direct-to-consumer and wine club operations, today announced its annual Wine Club Symposium, a free two-day virtual event taking place September 15 and 16. The event, which drew 550 registrants in 2025, brings the direct-to-consumer community together to learn from one another and strengthen the wine club.

The Symposium exists because the wine club matters. It is the most dependable recurring revenue a winery has, and it is under real pressure. Tasting rooms, still the main way wineries sign up new members, are seeing softer traffic, which makes acquisition harder. Retention is getting tougher too, as long-time members age and shifts in drinking habits, including the effect of newer medications, change how much they buy. vinSUITE hosts the Symposium each year to help wineries meet these challenges the way the industry always has, by sharing what is working. The event is free by design, built to bring the community together and leave every winery better equipped than it arrived.

“Every winery is wrestling with the same questions right now, and no one should have to figure them out alone,” said Jimmy Wu, president of vinSUITE. “We bring in the specialists who see across the whole industry so our community can learn from the best in one place. We are here to send people home with something they can actually use.”

Across six sessions, the Symposium brings together the specialists wineries rely on, spanning club logistics, email, member discovery, generational strategy, and the data behind it all.

The two-day agenda:

Tuesday, September 15

• 9:00 to 10:00 AM. State of the Industry: What the Data Says About the Future of Wine Clubs.
  Rob McMillan of Silicon Valley Bank and Jimmy Wu of vinSUITE.

• 10:00 to 11:00 AM. Delivering Loyalty: Insights & Data to Power Your Next Club Release.
  Karin Strykowski of Wineshipping.

• 11:00 AM to 12:00 PM. Your Next Club Member Is Already on Your List.
  Erica Walter of Email Mavens.

Wednesday, September 16

• 9:00 to 10:00 AM. The Generational Shift in Your Wine Club.
  Megan Currie of Wine Club Professional Network.

• 10:00 to 11:00 AM. Getting Found: How Wine Clubs Win Share of Mind When Search and the Market Are Changing.
  Pamela Snyder of Digivino, and Van Potts of Preston-Layne & Partners.

• 11:00 AM to 12:00 PM. Managing Up for Wine Club Managers: How to Be Heard by the People Above You.
  Liz Mercer of WISE.

Registration is free and open now at https://event.gotowebinar.com/event/f6f96c56-7abb-43c1-9cd0-3566b6b38d05. Recordings will be available to registrants following the event.

What Wineries Are Learning About Retention from LEGO and Starbucks

Every industry has moments where an outside perspective changes how it operates.

Restaurants borrowed reservations software from airlines. Fitness studios borrowed subscription models from streaming platforms. Hotels borrowed loyalty tiers from credit card companies.

The wine industry is due for a similar borrow.

At the recent Beyond Wine webinar with WISE Academy, Jimmy Wu and Liz Mercer walked through seven customer growth strategies that high-performing industries have quietly mastered. Three of those stood out as immediately usable for winery DTC teams, and none of them require new technology or a bigger budget.

Former members are alumni, not ex-customers

The sharpest moment from the session was Liz Mercer's reframe of how wineries treat cancellations.

"Ex-boyfriend is a negative connotation," she said. "Alumni is a positive one."

Most wineries treat a cancelled member like an ex. Paperwork requirements. Charge-back threats. Forced final shipments. A cold "please put your cancellation in writing" email.

The industries with the highest re-engagement rates have flipped that entirely. Universities send alumni magazines for decades after graduation. Fitness studios keep sending curated content and reactivation offers to former members years after they cancelled. The relationship stays open even when the transaction stops.

The mindset is simple: just because a member quit the club doesn't mean they quit the brand.

Jimmy Wu shared his data from his time working in other industries. Companies that continue thoughtful, high-quality communication with former customers see about 4% reactivation. Companies that cut them off see less than 1%. That's a fourfold difference on a segment most wineries treat as dead.

The winery version doesn't require a new system. It's a segment in your CRM, a quarterly "we miss you" touch, an invitation to a release party, or a mailing list for their favorite varietal. It's making cancellation itself easy. Skip. Pause. Downgrade. All the options that let a member step back without stepping out.

The wineries who do this well know that a member who leaves warmly often comes back. The ones who make cancellation feel like a bad breakup rarely see them again.

Give customers ownership, not just discounts

The second mindset shift is about how loyalty actually works.

Jimmy told the story of LEGO Ideas, the program that lets fans submit original designs, rally community support, and see winning concepts become real products. The reward isn't the discount or the finished set. It's the pride of having helped create something.

Liz translated it to wine immediately. What if your top 10 club couples helped blend a wine before release? What if your best members previewed a new tasting experience and gave feedback before you launched it? What if a small group voted on the theme of the next release event?

The winery version doesn't need to be a full program. It can start with one experiment. Invite five loyal members to preview an unreleased wine. Ask ten club members to weigh in on the next pickup party format. Let a member group name a proprietary blend.

The mindset behind all of it: participation says "you belong here" in a way that discounts never can.

Discounts train customers to wait for the next promotion. Ownership creates evangelists who tell their friends about the wine they helped make.

That kind of loyalty compounds. Discount loyalty doesn't.

Feedback is a competitive edge, not a nice-to-have

The third mindset that stood out was continuous customer feedback. And it stood out partly because of how few wineries are doing it.

The Wine Club Scorecard data we've been reviewing shows the same pattern the webinar surfaced. Very few wineries have any formal customer feedback loop. Not a transactional survey after a pickup. Not a relational NPS check every six months. Not a single qualitative conversation with a top member.

Think about how Starbucks Rewards works. Every purchase generates a data point. Every visit gets a receipt that invites feedback. Every star earned toward a free drink is a small signal about what the customer values. Starbucks isn't running the world's most sophisticated loyalty program because they got lucky. They built feedback into every touchpoint of the customer relationship, and they act on it.

Jimmy laid out three layers of feedback that industries with strong retention run consistently:

Transactional feedback. A short survey after a tasting, a pickup, or a customer service interaction. "How did we do?" One question, sent in the moment the experience is still fresh.

Relational feedback. A recurring survey like Net Promoter Score, sent every six to twelve months, asking a single question: how likely are you to recommend us to a friend? The number itself matters less than the trend.

Qualitative feedback. Actual conversations with top customers. Not a form. A phone call, a private tasting, a 20-minute chat that surfaces the "why" behind the numbers.

The wineries with the strongest retention are running all three, quietly, as a Monday morning habit. Most wineries are running none of them.

Feedback is one of the cheapest, highest-signal tools a winery has. It gets skipped because nobody built it into the operational rhythm.

Where to start

If all three mindsets feel like a lot to tackle at once, Jimmy's closing advice from the webinar was the most practical thing said the whole hour.

Aim small. Miss small. Experiment.

Don't build a full alumni re-engagement program. Send one warm email to your ten most recent cancellations and see what happens.

Don't launch a full LEGO Ideas equivalent. Invite five members to preview one wine and see how they respond.

Don't roll out an enterprise-wide NPS system. Send a one-question survey to your current club members and see what the number tells you.

The wineries doing this well started small. And then they iterated.

The full Beyond Wine webinar with WISE Academy is available now: https://attendee.gotowebinar.com/recording/3496552986470931033

Book a demo with vinSUITE to see how the platform surfaces the data behind these mindsets.