Winery DTC Customer Segmentation: Six Data Segments Every Wine Brand Needs with Paul Leary
Paul Leary learned about data the hard way. In his mid-twenties, heading up DTC for Duckhorn Vineyards under founder Dan Duckhorn, he spent years wrestling with a legacy system that made him mine and dig for every piece of customer information he wanted. That friction turned into discipline. He learned to be curious about data because he had no choice, and that habit of curiosity eventually became the foundation for everything he has built since. He went on to found Blackbird Vineyards in Napa Valley, launching the brand on Salesforce in 2007 when most small wine companies were still using spreadsheets, and now runs Assemblage Strategy Group, where he helps wineries turn their customer databases from liabilities into assets.
He sat down with Lauren Heindel to walk through the six customer segments every DTC wine brand should be tracking, how to use them to communicate differently at every stage of the customer journey, and what a partnership with the Foo Fighters taught him about lead sources.
The most financially healthy wineries, according to InnoVint’s State of the Wine Business survey, maintain roughly a 65/35 DTC-to-distribution split. That ratio gives them better margins and more control over how their brand reaches customers. But maintaining that kind of DTC channel takes more than a wine club and an email list. It takes a genuine understanding of who is in your database, where each person is in their relationship with your brand, and how to communicate with them based on that. Most wineries have the data. Very few are using it well.
In this episode, we cover:
The current state of DTC across the four sales channels: in-person, e-commerce, membership, and outreach
The six customer segments every winery should be tracking and how the active/inactive distinction changes everything
Why most winery databases are less healthy than they appear, and how to actually assess database health
How to use automated tags to segment customers without a full CRM buildout
The right way to handle a wine club cancellation so you keep the customer even when you lose the member
How Paul's Foo Fighters partnership at Bottle Rock generated hundreds of thousands of dollars in DTC sales and why lead source was the key
The current state of DTC: four channels, uneven results
Before getting into segmentation, Paul offers a clear-eyed read on where DTC actually stands in California right now. The picture is mixed, and he breaks it down by channel.
In-person sales at tasting rooms are flat. The post-COVID travel rebound that drove strong POS numbers through 2022 and 2023 has settled. Napa and Sonoma have become expensive destinations for a significant portion of tourists, and foot traffic has not returned to its prior levels. Wineries that relied on walk-in volume are feeling that.
Membership and wine club are showing attrition. Subscription fatigue is real and not specific to wine. Consumers are auditing their recurring charges, and wine clubs are getting caught in that review.
E-commerce can work, but it requires investment. Brands running paid social and search advertising with clear return on ad spend targets are seeing results. Those relying primarily on outbound email campaigns to drive web sales are finding conversions harder to get.
Those that are committed to the channel and have intense discipline in the channel — and one of the topics we're going to talk about here shortly — high segmentation in the channel, are doing better.
Paul Leary , Founder
Assemblage Strategy Group
The fourth channel, which Paul calls outreach, is where he sees the most growth potential right now. Outreach means focused one-to-one communication: targeted emails, SMS, personal calls, and individual touches that treat a customer like a person rather than a list entry. It is labor-intensive. It requires segmentation. And it is working for the brands that have built the discipline to do it.
Before deciding where to invest your DTC resources, map your current sales by channel. If you do not know what percentage of your DTC revenue comes from in-person, web, club, and outreach respectively, you are making resource decisions without the information you need. Start there.
The six segments of winery customer data
The framework Paul has used since his Duckhorn days, refined through building Blackbird and sharpened through years of consulting, starts with three customer types and doubles them with a time element.
The three types are prospect, client, and member. A prospect has never made a purchase. A client has made at least one purchase. A member is enrolled in a recurring membership or wine club. These distinctions matter because each type represents a fundamentally different relationship with your brand and requires a completely different communication approach.
The time element transforms three categories into six. An active prospect has a recent create date in your system, typically within the past one to two years. An inactive prospect has been in your database longer than that with no purchase. An active client has made a purchase within a defined recent window. An inactive client has not purchased in a year or more. An active member is receiving current shipments. An inactive member has lapsed or canceled.
I don't think people look at their database as actively as they should. Just like they'd understand the health of their wine inventory and have to sell products while they're still in their prime, the database has the same mindset.
Paul Leary , Founder
Assemblage Strategy Group
The reason this matters is that most winery databases look healthier than they are. A brand with 50,000 names in its system might have a significant portion of those names as inactive prospects who entered the database years ago and have never purchased. Counting them as part of your active audience distorts every metric you use to make decisions.
Run a basic audit of your database before your next email campaign. Pull the percentage of your total records that have never made a purchase, and then within that group, how many have a create date older than two years. That number will tell you more about the actual health of your DTC operation than your total list size.
How to automate segmentation without a full CRM
The ideal infrastructure for this kind of segmentation is a proper CRM, like Salesforce Sales Cloud or HubSpot, that can automatically assign customers to segments based on defined criteria. Paul built Blackbird on Salesforce from launch in 2007 precisely because he wanted that automated classification capability.
But a full CRM buildout is not always practical for small producers. For wineries using wine-industry platforms like Commerce7, the answer is tags.
Tags are labels that can be applied to customer records either manually or, more importantly, automatically when a customer meets a specific condition. You can set a rule that automatically applies an “inactive prospect” tag to any customer whose create date is more than a year old with no purchase on record. You can trigger a tag when a membership lapses. You can segment active club members by the length of their membership, so a ten-year member gets tagged differently from someone who joined six months ago.
You want to make sure you can use some sort of automation around it. What you don't want is any sort of manual process that requires constant attention.
Paul Leary , Founder
Assemblage Strategy Group
The goal is a system you set up once, audit quarterly, and trust to reflect the actual state of your database without daily intervention. Once tags are running automatically, you can build email segments, marketing campaigns, and outreach lists against those tags in minutes rather than hours.
If you are starting with tags for the first time, pick the one segment that most affects your revenue and build it first. For most wineries, that is inactive clients: people who have purchased before but have not bought in over a year. That list, well-worked, typically shows faster ROI than any other segment because these people already know and liked your wine.
How to handle a wine club cancellation without losing the customer
One of the most common and costly mistakes Paul sees is what wineries do when a member cancels. The instinct is to process the cancellation and move on. The opportunity is to recognize that a canceled member is still a customer with real loyalty history, and to treat them accordingly.
When someone cancels after three years of membership, they do not stop being a customer. They stop being a member. That is a meaningful difference, and it should change how you communicate with them rather than whether you communicate with them at all.
Paul’s recommended approach starts with immediate acknowledgment: a personalized note, not a generic confirmation email, that thanks them for three years of membership by name and lets them know the relationship is not over. No call to action. Just recognition. Then, after a few months, a light check-in: how are the wines showing? What have they enjoyed? Still no push to rejoin. Then, once you have re-established dialogue, a targeted offer based on the specific products they purchased most during their membership, not a generic promotion.
They chose to cancel. They're still a customer. They just don't happen to be a member. It's incredible how many people just get dropped even though they show tremendous loyalty.
Paul Leary , Founder
Assemblage Strategy Group
The product targeting matters. Paul is specific about this: go back to what they actually bought from you, the varietal and designation that had the highest purchase frequency, not your newest release, not your highest-margin product. If they come back at all, it will be for what they already loved.
Build a post-cancellation sequence in your email platform before you need it. Most wineries handle cancellations reactively, which means the communication is rushed and generic. Having a three-touch sequence ready (immediate acknowledgment, three-month check-in, product-specific reactivation offer) turns a common churn event into a structured winback opportunity.
Customer acquisition: referrals, partnerships, and why lead source is everything
New customer acquisition is the hardest problem in DTC, and Paul’s answer starts not with advertising but with the customers you already have. Your most loyal active members are your best acquisition channel if you actually ask them to be.
Most wineries underuse their member base for referrals not because members are unwilling, but because no one has asked them clearly, equipped them with the story to tell, and given them a reason to bring people. When you do those three things, members who have been coming to your winery for years bring their networks. Paul is blunt about the policies that get in the way: tasting limits for members, for instance, work directly against this.
For acquisition beyond referrals, Paul points to strategic partnerships with complementary brands or events that share your target customer’s demographics, income level, and values. His example from Blackbird illustrates both the opportunity and the importance of data discipline in executing it.
In 2017, Blackbird had a retail location near Bottle Rock Napa Valley. Rather than competing with the festival for foot traffic, Paul reached out to a Live Nation contact he had met months earlier and proposed a retail pop-up with one of the headliners. The Foo Fighters partnership that resulted brought lines out the door and strong sales over three days. But the real outcome came from what he set up beforehand: a private URL for leftover inventory, shared by the Foo Fighters to their millions of social followers. Hundreds of thousands of dollars in sales over three weeks.
The part most people miss: every single one of those customers was tagged with a lead source of “Foo Fighters / Bottle Rock partnership.” That lead source distinction meant Paul knew exactly how to market to them going forward, which was differently from someone who had walked in off the street to taste Blackbird wine on a normal afternoon.
The right lead source allows you to re-market in the right way. That lead source is very different from someone that just comes in to taste the wine at another time.
Paul Leary , Founder
Assemblage Strategy Group
Every acquisition campaign you run, whether a partnership, a pop-up, a festival presence, or a referral push, should have its own lead source tag in your system. This costs almost nothing to set up and gives you the ability to evaluate what actually drove new customers and how those customers behave over time compared to customers from other sources.
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Frequently Asked Questions about Winery DTC Customer Segmentation
How do wineries segment their DTC customer data? +
Wineries can segment DTC customer data into six categories based on purchase history and time: active prospects (in the database but no purchase, create date within the past one to two years), inactive prospects (no purchase, create date older than two years), active clients (recent purchasers), inactive clients (no purchase in a year or more), active members (current wine club enrollees), and inactive members (lapsed or canceled club members). Each segment requires a different communication approach. The most practical way to manage this segmentation is through automated tags in platforms like Commerce7 or a dedicated CRM.
What is the difference between an active and inactive wine club member? +
An active wine club member is currently enrolled and receiving shipments on a regular cycle. An inactive member has either lapsed by missing multiple shipment cycles or has formally canceled their membership. The important distinction Paul Leary draws is that a canceled member is still a customer with a meaningful purchase history, and should continue to receive personalized, low-pressure communication rather than being dropped from contact entirely. The goal is to maintain the relationship so the door is open for a future reactivation.
How do wineries reactivate inactive wine club members? +
Reactivating an inactive wine club member works best through a sequenced approach rather than an immediate offer. The first communication should acknowledge their membership history personally with no call to action. A follow-up check-in several months later keeps the relationship warm without pressure. When a reactivation offer is eventually made, it should be based on the specific products that member purchased most often during their active period, not a generic promotion. Personalization based on actual purchase history significantly improves reactivation rates.
What is customer lifetime value in wine DTC, and how should wineries think about it? +
Customer lifetime value in wine DTC is the total revenue a customer generates across all purchases over their entire relationship with the brand. Paul Leary adds a useful layer: indirect financial value, which accounts for referrals a customer generates. A member who spends modestly but consistently brings new customers to the winery may have a total value, direct plus indirect, that rivals a high-spend customer who never refers anyone. Tracking referral sources alongside purchase history gives a more accurate picture of which customers are actually driving growth.
How do wineries use CRM for direct-to-consumer sales? +
Wineries use CRM platforms to automatically classify customers into segments based on purchase behavior and time criteria, trigger personalized communication sequences based on where a customer is in their journey, track lead sources so acquisition campaigns can be evaluated and optimized, and identify product affinity by customer so reactivation and upsell offers are targeted rather than generic. Full CRM platforms like Salesforce or HubSpot offer the most capability. Wineries using wine-industry platforms like Commerce7 can achieve meaningful segmentation through automated tagging without a full CRM buildout.