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The World Is Your Tasting Room: How Any Winery Can Take Their Show on the Road (and Across the Globe!)
Let’s be honest: There’s a certain magic to pouring wine in your own tasting room—the clink of glasses, the sunlight through the vines, the laughter echoing off the barrel room walls. But what if you could bottle that magic and uncork it anywhere in the world?
Today’s top-performing wineries aren’t just waiting for guests to walk through their doors. They’re packing their corkscrews and passports, finding their biggest fans where they live, work, and play—from the next city over to the far side of the globe. Welcome to the golden age of wine roadshows—and, now, globetrotting wine adventures!
Why Travel? Because Wine Is About Connection
Wine is the ultimate connector. It brings people together and creates memories, whether it’s a backyard BBQ in Austin or a sunset dinner on the Amalfi Coast. Your most devoted club members and best customers crave those connections—and they’re hungry (and thirsty) for experiences that go beyond a traditional visit. Don’t take our word for it, though! Look at what an actual member had to say about a trip to Italy with their favorite wine club:
“We recently traveled to Northern Italy hosted by Judd’s Hill Winery, and coordinated by Ciao Andiamo. What an amazing experience!! The owners of Ciao Andiamo, Max and Cristiana, traveled with us and made the trip outstanding! Every detail was handled with perfection…When requests were made, especially when the requests were asking above and beyond the norm, both Max and Cristiana came forward and made things happen!! The people in their two offices, New York and Italy, were extremely capable of handling any of our needs.”
– Tim A.
Kenny Kim Photography
When you take your show on the road, you meet fans on their turf. You make it easy for your top customers to bring friends, family, and business colleagues into your orbit. You turn club shipments into community, and members into loyal brand ambassadors. And when you go international? Well, that’s when the stories—and the Instagram posts—get really good.
Ready, Jet Set, Pour: Going Global with WISE Trusted Travel Partners
You don’t need to reinvent the wheel (or re-learn the language of Italian train schedules) to bring your winery’s hospitality abroad. We’ve seen firsthand how game-changing the right travel partners can be for creating unforgettable international experiences.
- Ciao Andiamo takes the stress out of Italian wine adventures. Imagine hosting your club’s top tier on a private vineyard tour in Tuscany, complete with truffle hunting and chef-led dinners. You pour the wine—they handle the magic.
- Expedia Wine Club Cruises lets you turn a club shipment into a floating festival. Picture your brand headlining a Mediterranean cruise, offering exclusive tastings on board and shore excursions to historic cellars. This is how you move from “club” to “cult following.”
These experiences aren’t just perks—they’re loyalty superchargers. Members who travel with you become your best marketers (and, let’s face it, they’re probably the ones posting the most on social, too). Now with Expedia Wine Club Cruises, Director of Wine Cruises Tom Blackwood hosted over a dozen cruises when he was a winery DTC Director. He commented “The relationship changes dramatically with Members who have cruised with you compared to average Members. The are more loyal, and refer other members, often bringing them along on the trip. Once you have broken bread together, you will be friends for life!”
Don’t Forget Home Base: Roadshow Events Across the US
Not ready for an overseas adventure just yet? Or maybe your members want something closer to home? Domestic roadshows are still the gold standard for deepening relationships and recruiting new fans.
Does that thought of using a Member’s powder room seem a bit daunting? Our friends at Birch Road have reinvented the private club for modern wine lovers. Their stunning venues in cities like Chicago, Seattle, and Denver are perfect for curated, invite-only winery pop-ups. No stuffy clubs, just great spaces for you to pour wine for the right crowd – your fans and their members. Get to know Birch Road. “The Birch Road team provides great hospitality for their members and also provided a perfect context for us to show our wines. The members were highly engaged with our presentation and subsequently enthusiastic with their purchases as well. We look forward to returning to any of the Birch Road locations when the time is right.” – Steve White, National Sales Manager, Dunham Cellars
How to Get Started: Plan, Partner, Pour
Feeling inspired? Here’s how to make your next roadshow—domestic or international—a smashing success:
• Start with your super fans. Who are your best members, customers, and advocates? Where do they live, travel, and celebrate?
• Pick the right partners. Don’t try to do it all alone — you have enough going on. WISE’s trusted (and well vetted!) travel experts can make even the wildest ideas feel easy and seamless.
• Give it a story. Create a unique theme or angle for each event. Is it a “Passport to Pinot” in Portland? Or “Chianti with the Crew” in Siena?
• Capture every moment. Hire a photographer or encourage attendees to share their best snaps. The ROI on user-generated content? Priceless.
• Follow up like a pro. Make every guest feel like a VIP—because they are.
Ready to Take Flight? Here’s Your Next Step
If you’re ready to take your wine club beyond your tasting room—whether down the street, across the country, or around the world—now’s the time.
Sign up for WISE #222: Roadshow Events to learn the nuts and bolts of planning, promoting, and executing unforgettable events, wherever your members may be.
The world is waiting. So is your next club member. Let’s go!
In Tough Times, Every Guest Counts: Why Mystery Shopping New Tasting Room Staff Is More Essential Than Ever
Let’s face it—these are tough times. As the economy shifts and visitor traffic ebbs and flows, wineries are tasked with doing more with less. That means every single guest matters more than ever, and every interaction counts. The stakes are high, and there’s no room for guesswork when it comes to hospitality and sales.
Enter mystery shopping.
For nearly two decades, WISE has been quietly—and powerfully—supporting wineries by providing unbiased, expert insights into tasting room performance through our Mystery Shopping Program. Whether you’re onboarding new team members or sharpening the saw for seasoned staff, mystery shopping is the ultimate mirror. It reflects not just what your guests are experiencing, but how those experiences are impacting your bottom line.
Why Mystery Shopping Matters for New Staff
New hires may arrive with enthusiasm, but they also come with uncertainty. What exactly does “great hospitality” mean at your winery? What does a successful club pitch sound like? How do we encourage guests to stay in touch without sounding like we’re reading from a script?
Mystery shopping provides a safe, clear, and constructive way to answer these questions. It sets expectations and reinforces training through real-world scenarios. Rather than relying on guesswork or assumptions, wineries can ensure their teams are aligned with brand values and best practices right from the start.
The Hidden Opportunities in Every Guest Interaction
We know it’s not just about first-time visitors. Our data shows that existing wine club members—and especially their guests—are a goldmine of untapped opportunity. These VIPs already love your brand. Their guests are often just a few great touchpoints away from becoming loyal customers themselves. Are your teams making the most of those moments?
A mystery shopper can tell you.
What’s Working. What’s Not. And What to Do About It.
WISE Mystery Shopping evaluates staff on key performance indicators that are proven to drive sales and deepen relationships. We don’t just highlight what went wrong—we celebrate what’s going right and offer strategic recommendations for leveling up performance. Whether it’s asking for the sale, inviting guests to join the club, or collecting contact data, we focus on the behaviors that move the needle.
You’ll get detailed reports, side-by-side comparisons, and coaching-based feedback that’s not only actionable—it’s transformational. Teams often feel more motivated, more confident, and more connected to their purpose when they understand how their actions impact the winery’s success.
A Free Tool to Start With
We make the WISE Mystery Shopping Score Card available for free on our website. It’s a valuable tool that can be used right away—even without a formal mystery shop. One way we recommend using it: pair up new team members with a star performer and send them to experience your competition together. Afterward, have a discussion about how the experience matched up to your winery’s standards. This creates alignment and insight before they even greet their first guest.
Making the Most of Every Opportunity
In challenging times, there’s a temptation to cut corners. But the wineries that invest in training, accountability, and continuous improvement are the ones that emerge stronger. Mystery shopping isn’t just a training tool—it’s a strategic advantage.
So whether you’re onboarding your newest host or refreshing a rockstar team, WISE Mystery Shopping is here to help you create consistently memorable, profitable, and brand-building guest experiences.
Don’t leave it to chance. Know what’s happening in your tasting room—and use it to grow.
👉 Learn more and download the free Mystery Shopping Score Card
Is the Pendulum Swinging Back? Rethinking Wine Experiences in a Shifting Landscape
Like any other industry, the wine industry is cyclical. What goes around tends to come back around. And what can we learn from those trends—besides the fact that leg warmers were never cool, even in the ’80s?
Wine hospitality began with casual, bar-style tastings—one host, multiple guests, and a quick pour-and-go approach. Over time, we introduced more educational options: tours, guided tastings, and eventually, more intimate seated experiences.
Then came the pandemic. It acted as a litmus test for tasting room strategy and showed—on a large scale—that time with guests matters. More time meant greater satisfaction, higher wine sales, and more club signups.
The reservation model also revealed something powerful: those who took the time to book were more intentional. They came to taste and to buy. And the ROI of seated, guided experiences reflected that.
Fast-forward five years, and many tasting rooms now default to seated tastings. But… is the pendulum swinging back?
We’re hearing about declining visitor traffic. And we know that younger consumers—Gen Z especially—value spontaneity and unique experiences. Are our structured reservations and seated formats limiting our ability to connect with this emerging audience?
Maybe it’s not about reverting or reinventing—maybe it’s about reimagining what hospitality can look like in today’s landscape.
Because one size doesn’t fit all.
Doing More with Fewer Guests
In a climate of reduced foot traffic, the focus shifts from volume to value. Every guest who walks through the door becomes more important—and that means delivering an experience that resonates and converts.
But how do we create something that feels curated without losing the flexibility that today’s guests crave?
Blending Structure with Spontaneity: 10 Creative Ideas
Here are ten ways to offer tailored wine experiences that are structured enough to deliver consistent quality, but flexible and fun enough to keep things fresh and discoverable:
1. Core Reservations + Walk-In “Bar Bites”
Keep your seated tastings by reservation, but offer a smaller, casual flight for walk-ins. A “three-wine pop-in” or “winemaker’s daily pick” can satisfy spontaneous visitors without disrupting operations.
You can also hold back a few tables or bar spots for walk-ins while keeping most for reservations. This allows you to accommodate both planners and spur-of-the-moment visitors.
2. Timed, Mini Experiences
Create short-form offerings like a 20-minute barrel tasting or mini cheese pairing. Perfect for guests who didn’t plan ahead but still want something memorable.
3. Hybrid Events with Loose Structure
Open house-style events with roaming tastings, self-guided vineyard walks, and light educational signage blend choice with intentional engagement. These are especially appealing to locals, Gen Z visitors, or casual groups.
4. Winery “Passport” or Scavenger Hunt
Create a fun, gamified element—stamp cards for different experiences or a vineyard scavenger hunt with hidden clues around the property.
Delight curious guests with unadvertised bonus pours or experiences when they ask the right questions or engage with their host. (“Did you notice the owl carving? You get a bonus pour!”)
This builds engagement and encourages repeat visitation—without the need for rigid structure.
5. Walk-In Surprises and Personalized Experiences
Guest of the Day:Surprise one walk-in group each day with an unexpected upgrade—a seated tasting, bonus pour, or mini tour. It builds buzz and gives people a reason to roll the dice and stop in.
Pre-Visit Personalization: Use reservation systems to ask a few light questions (preferences, wine knowledge, etc.). This helps hosts tailor the experience just enough to make guests feel seen—without requiring a totally different format.
It’s Not Either/Or—It’s Yes, And
Offering both structure and spontaneity isn’t about creating two separate systems. It’s about weaving flexibility into your existing framework. It’s about training teams to read the room, offer options, and pivot when needed.
A seated tasting doesn’t have to be formal or rigid. A walk-in bar flight doesn’t have to feel generic. The difference is in the execution. It’s in the invitation. It’s in the mindset.
As traffic shifts and guest expectations evolve, the wineries that will thrive are those that offer memorable, flexible, and profitable experiences to everyone—from the planner to the wanderer.
So maybe the pendulum isn’t swinging all the way back — it’s just settling into a new rhythm.
And that rhythm? It’s all about balance.
Fewer guests doesn’t have to mean fewer sales. What small shifts could lead to big results in your tasting room?
Reimagining the Water Cooler: Building Connection in Remote DTC Wine Teams
The COVID-era shift to remote and hybrid work brought many benefits: flexibility, broader talent pools, and increased autonomy. But it also came with a major cost—especially for those in the DTC wine world: we lost the spontaneous learning and camaraderie that happened naturally when we shared the same space.
Gone are the days of overhearing a colleague crush a club sales call or brainstorm a great pitch for a wine event. We don’t gather in the break room to compare Survivor predictions or poke our heads over a cubicle to troubleshoot a customer issue. Those moments—informal, unscripted, and deeply valuable—were how culture was shared, best practices spread, and new team members learned the ropes.
Now, our teams are spread across time zones and working from home. Our phone sales specialists might be in Oregon, our club manager in Omaha, and our fulfillment team hours away. How do we recreate that sense of connection and community when we don’t bump into each other anymore?
Why “Water Cooler Culture” Mattered More Than We Realized
Water cooler talk wasn’t just about gossip or pop culture—it was a vital source of organic professional development. Here’s what we lost:
- Peer-to-peer learning from overheard calls and casual feedback
- Real-time coaching from seasoned team members
- A shared sense of team identity and culture
- Opportunities to celebrate wins and troubleshoot losses
In the wine DTC world, where storytelling, connection, and nuance matter, these shared moments helped shape how we represent our brand voice and deliver exceptional hospitality.
Recreating Connection in a Distributed World
We can’t go back to those spontaneous hallway chats—but we can design new systems that foster similar connections, collaboration, and mentorship.
Here’s how:
- Schedule “Virtual Water Cooler” Time
Dedicate 15–30 minutes each week for unstructured team time. No agenda, just an open Zoom or Teams room where people can talk about whatever they want—last night’s game, the weird club request they got, or the new rosé they tasted. These moments build trust, boost morale, and give space for organic conversations.
- Use Tools to “Listen In”
Create opt-in Slack or Teams channels where team members can share:
- Great customer interactions
- Call recordings or summaries
- Interesting objections they handled
- Marketing copy they’re testing
Encourage voice memos or Loom videos to bring tone and storytelling into the mix.
- Create a “Call of the Week” Culture
Designate one standout call, email, or club interaction each week to spotlight. Ask the person to break it down: what worked, what they’d do differently, what the outcome was. This is a modern version of overhearing the rockstar down the hall.
- Build a Buddy System
Pair newer employees with veterans for monthly 1:1s—not formal training, just peer conversations. Encourage them to swap stories, compare techniques, and build relationships. This mimics that “tap on the shoulder” access to expertise we’ve lost in remote environments.
- Bring the Team Together—Digitally and Physically
Hold quarterly virtual all-hands that focus on stories, not just numbers. Celebrate wins, share guest feedback, and invite different departments to spotlight what they’re working on. If budget allows, organize annual in-person gatherings or retreats to build deeper connections.
- Standardize and Share Best Practices
Turn spontaneous insights into shared tools. Use a central knowledge base (Slack, Teams, Google Drive, Notion, Bloomfire, Guru, etc.) to house:
- Call scripts
- Objection-handling guides
- Successful club email templates
- Event hosting checklists
Make it easy for wisdom to be captured and shared.
- Celebrate Curiosity
Encourage team members to bring one question to each meeting:
- “How do you talk about the library release with high spenders?”
- “What do you say when someone says: ‘I only like whites.’?”
- “What’s your go-to move to increase club retention?”
These questions spark storytelling and collective problem-solving—hallmarks of a strong DTC culture.
Final Thoughts: The Future of Culture Is Intentional
The spontaneity of water cooler moments may be gone, but the human need for connection and shared learning is as strong as ever. As winery leaders, we need to be deliberate in creating spaces for that connection to thrive in new ways.
It takes more effort to build community across screens and time zones—but it’s worth it. Your team is your brand. The more connected they feel to each other, the more connected your customers will feel to your wine.
Let’s not mourn the water cooler—let’s reimagine it.
Need help fostering team culture, communication, and coaching for your remote DTC crew? WISE can help. Our custom workshops and leadership coaching programs are designed to support winery teams—no matter where they’re based.
In Case You Missed It: Q1 Round Up
Hard to believe, we are a quarter of the way through 2025!
It seems like just yesterday we were starting 2025, but here we are, 90 days in to the "new" year. Here are a few things you may have missed, things that caught our eye (or ear), and a few actionable ideas for the next quarter.
2024 Annual Report Card - WISE Mystery Shopping Triple Score
In early 2025, we released our Annual Triple Score Report Card. While Mystery Shopping covers over 75 criteria points, these three are perhaps the most important. How often are our Mystery Shoppers asked buy wine, how often are they warmly invited to join the wine club, and how often are they asked to keep in touch via joining the mailing list? In 2024, we saw a dramatic decline in Triple Score averages. In particular, data collection is critically low at just 18%—meaning we’re only asking fewer than one in five guests to keep the conversation going. Wine clubs work because people DO like to be part of them (did you know the average guest belongs to five wine clubs?). Yet, they’re only hearing about club offerings in one out of three visits. The proof is in the pudding—asking for the club sign-up is vital! The good news is that our shoppers were asked to purchase wine, but often times it was "Would you like to purchase a bottle?" or "You only need to purchase X bottles to waive the tasting fee" - clearly there is some work to be done to increase AOV by leaving it opened ended. To take it the next level, try asking if guests would like to purchase "Some" of their favorite wine (and remind them of their favorite!). "Some" is subjective, whereas "A bottle" is clearly defined. Try it and report back!
Get to know the WISE Partners
WISE Co-Founder and Chairwoman Lesley Berglund was profiled on Small Fortune Podcast with Carol Collison. Listen as they discuss learnings from over 30 years in pioneering winery Direct to Consumer sales and marketing.
Our Glue, and Partner, Jennifer Warrington was interviewed by George Christie on the Wine Industry Insiders. They discuss where she and her accent are from, her love for traveling, how she landed in her role at WISE, a bad secret-shopping experience she once had, and much more!
WISE Partner Liz Mercer was recently interviewed by Lawrence Francis on Interpreting Wine. She shared her journey from homelessness to finding meaning in hospitality and serving others.
Calling All Wineries! Industry Trends Survey in Shipping Subsidization
Wineshipping is conducting a brief survey to learn how wineries approach shipping subsidization. Whether you offer flat-rate shipping, discounts, or other incentives, we want to understand what works for you and your customers. The survey is anonymous and will remain open until April 15. We’ll compile the results and share key insights with the industry.
It only takes a few minutes—thank you for sharing your experience!
Take the survey: https://survey.zohopublic.com/zs/hfBtlF
Let's Get Together!
Join us at Wineshipping HQ in Napa on April 30 from 2:00 – 5:30 PM for an exclusive in-person event featuring sessions from Commerce7, RedChirp, Wineshipping, and WISE.
You'll learn:
- How modern technology drives DTC success
- Customer engagement tactics that boost sales
- Operational efficiencies to streamline fulfillment
This is a must-attend event for wineries looking to grow with the right technology and proven strategies. RSVP here.
Invest In Your Team - Let's Get Ready for the Season
With guest counts in flux, and uncertainty ahead, now is the time to ensure we make the most of every guest encounter. From cost effective live Zoom courses, to tailored on site coaching, WISE has solutions to build your team's DTC skills. Email us for a free consultation!
Time-Sensitive: Join the WISE Travel Series
Wineries know that great wine isn’t just about what’s in the glass—it’s about the people we share it with. Now, imagine taking that connection beyond the tasting room and into the world.
The WISE Travel Series is designed to help wineries deepen relationships with their biggest fans through immersive travel experiences. Whether it’s sipping Brunello in Tuscany with Ciao Andiamo or sailing through legendary wine regions on the rivers of Europe with Expedia Wine Club Cruises, these journeys create unforgettable moments that strengthen loyalty and build lifelong brand advocates.
Since our wine club members and best customers are already traveling the world, why not join them? Sharing meals, exploring vineyards, and discovering new cultures together fosters an unparalleled bond—one that keeps your winery top of mind and heart.
We’re teaming up with trusted travel partners to make hosting your own winery trip seamless and rewarding. Want to learn more? Join our upcoming info sessions and start planning your winery’s next great adventure. Learn how your winery representatives may travel for FREE when meeting guest minimums.
When WISE wineries book through either Ciao Andiamo or Expedia Wine Cruises, they will receive a WISE coaching package to help market the adventure.
Ciao Andiamo
Ciao Andiamo is a boutique travel outfitter curating authentic, immersive journeys throughout Italy. Their multi-day wine adventures delve deep into the regions of Italy, beyond the typical tourist path, and are led by one of their three co-owners & certified sommelier Cristiana, making for the ultimate insider’s experience. Cristiana, together with fellow co-owners Max & Jon, invite you to enjoy a glass of wine while learning about how you might take your Wine Club and winery fans to Italy!
Meet Ups - RSVP here for one of the below meetings:
March 4, 3:30pm Sonoma, CA
March 5, 3:30pm St. Helena, CA
Monday 17 10am, Zoom
Expedia Wine Cruises
Expedia Wine Cruises are designed for a limited number of guests, allowing each passenger the opportunity to better interact and dine their wine host. These special voyages have the wine enthusiast at heart that explore both favorite and exotic destinations in the company of fellow enthusiasts from all over the world. Due to the limited availability, these cruises do sell out in advance. Hear from Tom Blackwood, who has taken hundreds of his Wine Club members on elegant river cruises throughout Europe. Tom will share how the process works, and what he has learned while traveling with members.
Meet Ups - RSVP here for one of the below meetings:
March 6, 3:30pm Napa, CA
March 20, 1pm ZOOM
Combine this with a smart travel program, and you’ll have an unbeatable formula for customer engagement and brand growth. Let’s see where 2025 takes you!
Hospitality: A Noble Profession that Requires Diverse Skills
In the world of hospitality, there’s a misconception that offering service is just a job—something anyone can do with minimal training or effort. Yet, anyone who has truly excelled in this profession knows the truth: hospitality is a noble calling. It requires a combination of innate qualities and cultivated skills to succeed, creating exceptional experiences for every guest who walks through the door. Hospitality isn’t merely about serving; it’s about creating emotional connections and relationships, telling stories, and making guests feel seen, valued, and celebrated.
At the heart of this calling lies the hospitality heart—a genuine love for serving others. It’s the difference between a transactional experience and a transformational one. But even with an inherent hospitality heart, this profession demands diverse, professional skills to truly excel.
Hospitality Heart: The Foundation of Exceptional Service
Hospitality begins and ends with heart. It’s an unteachable quality, an innate drive to care for others, to anticipate needs, and to bring joy. Guests feel it when they are greeted warmly, listened to attentively, and treated as more than just a customer or a number.
It’s easy to spot someone with a hospitality heart—they radiate kindness and enthusiasm, even in challenging situations. This intrinsic quality fuels the rest of the skill set required in this profession, making the challenges feel rewarding and the successes feel deeply meaningful.
But having heart is only the beginning. To thrive in hospitality, professionals need a toolkit of advanced skills that help them deliver consistent, exceptional experiences.
Building Rapport: Connecting on a Human Level
Hospitality is, at its core, about relationships. Guests aren’t just purchasing a service or product; they’re investing in an experience. To create that connection, building rapport is key.
There are many ways to build rapport/trust from the initial greeting and icebreaker to engagement tactics like storytelling and analogies to open-ended questions and tailoring experiences. Building rapport begins with active listening, understanding the guest’s preferences, and engaging with them in meaningful ways. Whether it’s remembering a returning guest’s favorite wine or asking thoughtful questions about their preferences, these small interactions establish trust and create loyalty.
Rapport-building also extends to managing difficult moments with grace and professionalism. Every interaction is an opportunity to show empathy and strengthen relationships. It’s this human connection that sets exceptional hospitality professionals apart.
Storytelling: Bringing the Brand to Life
Every winery has a story, and in the hospitality industry, that story is an essential part of the guest experience. Whether it’s the tale of how a family vineyard began, the passion behind crafting a new wine blend, or the inspiration for a unique label, storytelling creates emotional connections.
Guests want to feel part of something bigger—something with roots, history, and heart. Professional hospitality requires the ability to weave these narratives seamlessly into the experience. A well-told story about a wine’s origin or production process can inspire guests to purchase a bottle or join the wine club to stay connected to the brand’s journey.
Professional Selling Skills: Matching Guests with Their Perfect Experience
Hospitality isn’t just about offering great service—it’s also about delivering value, which often involves increasing wine sales and building loyalty through club memberships.
True salesmanship in hospitality doesn’t feel pushy or transactional. Instead, it feels like matchmaking. It’s about understanding the guest’s needs, preferences, and desires, then thoughtfully recommending wines, experiences, or memberships that align with those.
For example, guiding a guest through a tasting flight becomes an opportunity to learn about their preferences. Did they love the bold cabernet? A gentle suggestion to take home some bottles—or better yet, join the wine club for exclusive access—can enhance their experience. A well-executed wine club pitch isn’t just about boosting sales or commissions; it’s about helping the guests continue their journey with the brand.
Data Collection: Enhancing Future Visits
One of the most critical, yet often overlooked, aspects of hospitality is capturing guest data to personalize future interactions. Whether it’s through email sign-ups, detailed notes about their preferences, or tracking their favorite wines, collecting this information allows wineries to elevate the guest experience.
Imagine a guest returning for a second visit, and the host remembers not only their name but also their love for big, bold reds. This level of personalization fosters loyalty and turns one-time visitors into lifelong customers. Every interaction becomes an opportunity to build a deeper connection and keep the guest engaged with the brand, whether through targeted emails, exclusive offers, or personalized wine recommendations.
Why Diverse Skills Matter
Hospitality professionals wear many hats. One moment, they’re storytellers, sharing the brand’s history with passion and authenticity. The next, they’re salespeople, helping guests find the perfect wine. They’re also problem-solvers, resolving challenges with creativity and poise, and data strategists, capturing information that will make future interactions even more impactful.
This diversity of skills is what makes hospitality so rewarding. Every day is an opportunity to grow, to learn, and to make a difference in someone’s experience. It’s a dynamic, challenging, and deeply fulfilling career path for those who have the heart.
Creating a Culture of Excellence
For organizations, fostering this level of professionalism starts with cultivating a culture that values hospitality as a calling. It means hiring for heart, providing training that develops professional skills, and celebrating the successes that come from exceptional service.
By investing in their teams, businesses can create environments where hospitality professionals thrive. Training programs help teams master the skills they need to succeed, from building rapport to professional selling and storytelling. When teams feel supported and empowered, they’re better equipped to deliver unforgettable guest experiences while driving wine sales and club memberships.
The Reward of Hospitality
Hospitality isn’t just a profession—it’s a way to make an impact, one guest at a time. It’s the joy of seeing someone light up when they discover their new favorite wine, the gratitude of a guest who feels truly seen and valued, and the satisfaction of knowing you’ve helped create a moment they’ll remember forever.
For those who feel the call of hospitality, the work is more than worth it. It’s a chance to combine passion, creativity, and skill to make a difference in people’s lives. And for businesses, it’s an opportunity to build teams that embody the very best of what hospitality can offer.
If you’re ready to take your team to the next level — enhancing their skills in sales, storytelling, and data collection — WISE is here to help. Together, let’s elevate the guest experience and celebrate the nobility of this incredible profession.
Hiring the Last Unicorn
Take a look at any number of Tasting Room Associate job ads, and it becomes apparent we need to hire unicorns – rare, mystical, and never seen in the wild except by a chosen few. We are seeking that blend of hospitality heart, wine knowledge, and hopefully sales skills. Every new opportunity to hire is the chance to go searching for unicorns, and luckily, there is a strategy to help find them!
First, let’s define what a successful DTC candidate needs to have.
- Hospitality Heart. A Hospitality Heart, which is impossible to train for, is something the candidate either has or not. It is the rarest quality, hidden, and can be bluffed if needed. WISE calls this Service Heart. In our Mystery Shopping, we are looking for Service Heart – the deep seeded desire of that teammate to be helpful, kind, and truly wanting to be of service, and not just there to punch a time clock and collect a paycheck.
At the Union Square Hospitality Group, Danny Meyer has taken great care to define their version of a Hospitality Heart as 51% emotional skills, and 49% technical skills. In Setting The Table, his book on creating a hospitality empire, he writes:
“To me, a 51 percenter has five core emotional skills. I’ve learned that we need to hire employees with these skills if we’re to be champions at the team sport of hospitality. They are:
- Optimistic warmth (genuine kindness, thoughtfulness, and a sense that the glass is always at least half full)
- Intelligence (not just “smarts” but rather an insatiable curiosity to learn for the sake of learning)
- Work ethic (a natural tendency to do something as well as it can possibly be done)
- Empathy (an awareness of, care for, and connection to how others feel and how your actions make others feel)
- Self-awareness and integrity (an understanding of what makes you tick and a natural inclination to be accountable for doing the right thing with honesty and superb judgment)”
However you define Hospitality Heart for your organization, be it 51%, service heart, emotional quotient, or whatever it is referred to in your organization, is the most critical attribute of successful candidate. A well written job ad, that calls out exactly how your organization defines hospitality to attract the right person.
2. Wine Knowledge. Wine knowledge (and passion) is important. Wine knowledge is not a Day 1 requirement but should be part of the onboarding process. There should be a balance of knowledge and passion. Have you ever walked into a tasting room, and the passion is off the charts, but the factual information is a little suspect? How about the opposite? In a tasting room, have you heard the host talk very knowledgably but is monotone and without passion? Take care to ensure your team is providing accurate information along with passion – inaccuracy is one of the quickest ways to destroy rapport and trust with wine savvy guests! While knowledge is important, the details are not what’s going to sell the wine. People buy with their emotions and are more likely to purchase if they like the person, if the host is showing passion. Which leads us to…
3. Sales Skills. The last part of being a unicorn is a firm understanding and ability to sell wine. We took great care to hire for heart, we can teach our brand story and build their wine knowledge, but how much energy are we putting in to teaching sales skills? Often times, we find great staff that are uncomfortable with sales. We find it is often passive with a “Oh, if a guest likes the wine, they will purchase or join the club”. It is not enough to share our love of the wines and brand, we have to see ourselves as the relevant matchmaker, taking the portfolio (of experiences, wines, club options) on one hand, and matching those to our guests’ preferences, needs, and desires. Sales come through superb service; it is an extension of the hospitality heart.
So, how do we go unicorn hunting? The hardest part of hiring a unicorn is ensuring that we’re putting our best foot forward with a well-written job ad, followed by a detailed job description. A well-crafted job ad should attract the right candidate, and scare off the wrong ones, and that is ok! Describe your company vision/mission/goals and culture, use emotive words to describe your ideal candidate, and even weave in quotes from other team members or social reviews. Paint the picture of the ideal candidate, the environment they can expect to find themselves in and will thrive in. This will help attract those rare, mystical unicorns.
https://wineindustrysaleseducation.com/hiring-the-last-unicorn/
WISE Up! Shaping Strong Leaders and Boosting DTC Sales in the Wine Industry
WHY WISE? WISE – which stands for Wine Industry Sales Education – we believe a rising tide lifts all boats and that the wine industry deserves strong leaders, healthy teams, DTC mastery and winery success. We serve by continually raising the bar for professionalism and leadership in the wine industry. We provide opportunities for experiential learning that changes behavior. We are wine industry leaders in professional development, focused on both DTC & General Leadership. We provide Relevant Classes, Mystery Shopping, Coaching, Consulting and Leadership Programs.
WISE
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WISE (Wine Industry Sales Education) offers a comprehensive curriculum designed specifically for wine industry professionals. Built from a belief that direct- to-consumer (DTC) results are the key to success in the wine industry, WISE offers the first wine industry education, training and certification program dedicated to DTC sales and marketing.
Investing in Your Team: Why Training Staff Matters Even More Than Ever Before
Uncertain times can feel like a game of survival for many in the wine industry. With tighter budgets, shifting consumer spending, and market challenges, it’s tempting to cut back on non-essential expenses like staff training and development. Yet, those who invest in their teams during tough times often emerge stronger, with a distinct edge that sets them apart from the competition. Perhaps we’re preaching to the choir, but for anyone who needs to ‘sell’ the concept to others, let’s explore why investing in training your team now is not only essential but could also be the key to long-term growth, stability, and resilience.
Elevating the Guest Experience: Training as a Core Strength
A well-trained sales team creates an unmatched guest experience that can directly impact your bottom line, especially when fewer guests may be walking through the door. Every guest interaction is an opportunity to build loyalty and increase conversions, whether through wine sales, club memberships, or brand loyalty. Well thought out onboarding, regular and consistent coaching, and ongoing sales training gives your team the skills they need to connect with guests authentically, respond to diverse needs, and personalize each experience in a way that creates lasting impressions.
Guests are more likely to return to places where they feel valued, respected, and delighted. With shifts in guest counts in every region, a well-trained staff is vital to the winery’s success. With well trained and frequently coached staff, even a lower number of guests can generate a significant impact, helping to steady sales in the face of reduced foot traffic. Danny Meyer (a New York City restaurateur and the Founder & Executive Chairman of the Union Square Hospitality Group) refers to the “constant, gentle pressure” of everyday manager/staff interactions to reinforce the standards:
"Constant, gentle pressure is about setting high standards, holding team members accountable, and correcting them — repeatedly, enthusiastically, and with kindness — when they start to drift from those standards. It’s also about accepting the infinite nature of this work. If you lead a team, this nudging and reminding literally never ends."
Investing in training can create a learning organization who is growing. It can create more employee engagement and productivity, boost morale and reduce turnover, and increase employee retention as well as attract new talent.
Building Sales Savvy and Driving Revenue
One Case Study of Companies with High Training ROI shares that companies investing in employee training saw an average of 24% higher profit. Another report shows organizations that invest in employee training are 11% more profitable than those who don’t.
The Association for Talent Development research lead one Chief Talent Officer to believe that “most organization’s should consider their training budgets as a percentage of payroll and plan on fluctuations in budget based on changes in strategy, operational requirements, or specific initiatives…organizations should be somewhere in the two to five percent of payroll range.”
A team that has received training in direct-to-consumer (DTC) sales techniques is far better positioned to drive revenue through effective, confident sales. In DTC sales, hospitality and sales are interwoven; employees who are trained to think of themselves as brand ambassadors and matchmakers for the guests’ preferences are inherently more effective at turning a tasting into a sale. Training equips staff with the skills and confidence to initiate conversations about wine purchases and memberships and to upsell or cross-sell when appropriate.
In a climate where every sale counts, skilled sales team members can make all the difference. How does your team stack up? Are they seeking the WISE Triple Score with every guest?
- Asking for the Order – in a brand appropriate, guest service focused way, it is critical that staff is asking every guest to purchase wine. Creating that FOMO, offering a value proposition they just can’t refuse, and reminding them of what they liked is critical.
- Warm, genuine invite to Wine Club – again, in a brand appropriate way, ensuring every guest has verbally been invited to the club, even the ones whom staff doesn’t think may want to join. Ensure the team is selling to the guests’ wallet, not their own. Let the guest decide. Right now, wineries are mentioning “Wine Club” less than 36% of the time when WISE Mystery Shopped. Any wonder club acquisition is down?
- Data Collection – for many brands, the key to successful sales online, over the phone, and via text is to have robust data collection happening in the tasting room. This goes beyond “transactional information” collected during the reservation or sales process but is rooted in the team thinking long term about each guest. Today’s visit is just one touch point in a long relationship, yet less than 24% of wineries are asking to keep in touch.
Strengthening Brand Consistency and Reputation
Trust is the foundation of brand loyalty – trust comes from consistency and quality. But how does an organization create and sustain this? Training and processes. If the learning process isn’t designed and planned, the outcome is unreliable and inconsistent. It can take just one breach of trust for a customer to never return again.
Brand reputation is built guest by guest, and in hard times, a consistent brand is a powerful differentiator. Well-trained employees serve as ambassadors for your values, quality, and authenticity. They know how to articulate the brand story, make guests feel welcome, and uphold high standards that earn trust and foster positive reviews. In this way, investing in staff training becomes an investment in your brand’s reputation.
Team members who feel they’ve been invested in will be more willing to recommend their winery. Positive employees are a significant contributor to company reputation.
Why invest in training team members? The real question is, why not?
About
About WISE
WHY: Strong Leaders. Healthy Teams. Successful Wineries. We believe a rising tide lifts all boats and that the wine industry deserves strong leaders, healthy teams, DTC mastery and winery success.
HOW: We serve by continually raising the bar for professionalism and leadership in the wine industry. We provide opportunities for experiential learning that changes behavior.
WHAT: We are wine industry leaders in professional development, focused on both DTC & General Leadership. We provide Relevant Classes, Mystery Shopping, Coaching, Consulting and Cabinet Programs.
At WISE – which stands for Wine Industry Sales Education – we offer a variety of courses, workshops, and coaching that are interactive and hands-on to help enhance your skills and advance your career.
Courses are designed to deliver take-home value using real-life, relevant examples through a combination of lecture, group exercises, and role play, these classes build on existing skills and teach best practices for meeting the demands of today’s changing DTC marketplace.
Courses are live – offered in-person and remotely – so that attendees gain ideas and insights as well as access to a community of their peers. With a true understanding of the value of our attendees’ time, our courses are succinct, efficient, and targeted, covering maximum material in a minimum of time.
Complete course descriptions are available online at www.WineIndustrySalesEducation.com, or for more information, call (844) 947-3498.
About WISE Coaches
WISE core group of coaches are each leaders in their field of expertise. Like WISE's founder, they are dedicated to raising the bar for consumer direct and management excellence in the wine industry.
Plan Ahead and Save
Pre-purchase educational credits and earn a 10% bonus on your commitment through the WISE Futures program.
Contact Us
Jennifer Warrington The Glue
Email: Jennifer@WineIndustrySalesEducation.com
Contact
Contact List
| Title | Name | Phone | Extension | |
|---|---|---|---|---|
| Chairman, Co-Founder | Lesley Berglund | lesley@wineindustrysaleseducation.com | 877-740-9473 | |
| Co-Founder | Mack Schwing | mack@wineindustrysaleseducation.com | 877-740-9473 | |
| The Glue | Jennifer Warrington | jennifer@wineindustrysaleseducation.com | 877-740-9473 |
Location List
| Locations | Address | State | Country | Zip Code |
|---|---|---|---|---|
| WISE | Po Box 2089, Napa | CA | United States of America | 94559 |
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