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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:

  1. 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.

  1. 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.

  1. 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.

  1. 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.

  1. 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.

  1. Standardize and Share Best Practices

Turn spontaneous insights into shared tools. Use a central knowledge base (Slack, Teams, Google Drive, NotionBloomfireGuru, 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.

  1. 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.

Learn more at wineindustrysaleseducation.com

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!

RSVP HERE

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.

  1. 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
WIN Expo Booth: 522

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?

  1. 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.
  2. 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?
  3. 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?

Taking It to the Streets

Overdependence on Tasting Room traffic as the sole driver to grow our DTC business has become problematic for all wine regions. Between fires, the pandemic, changing travel patterns many wineries have focused new efforts on building DTC customer bases from programs that they can actually control – DTC road show events.

WHAT
What do we mean by road show events?

  • Traditional Winemaker Dinners – This is not new. Wineries have been partnering with a local on-premise account for decades. Now, however, restaurants are looking to fill empty tables and may offer better options than ever before.
  • Wine Club Events – Also not new, but picking up a lot of momentum, especially since COVID. A great way to engage Current and Alumni Members, especially those who mention they don’t get to take advantage of their benefits.
  • Private Tastings – In a customer’s home or country club. They invite the Guests, often their very well qualified friends and associates. Afterall, birds of a feather flock together! There are obviously licensing and insurance concerns, so do be diligent in asking the right questions to protect the business.
  • Other Events – Sometimes with partners, could be winery or partner hosted, could focus on reaching new customers or serving current customers. Again, do your due diligence to protect the core business.

WHY
An Important, Often Overlooked Channel.

For wineries, the recent rise of Roadshow Events has opened the door to meet guests where they are, out in the market. This important new sales and brand building channel is here to stay.

From a consumer direct perspective, Roadshow Events have become an extension of the Events, Tasting Room, and Wine Club Channels, which is both exciting and necessary. Members are proud to welcome wineries into their homes, or meet them at a neutral location and bring their friends to experience the wine and brand, without having to leave their hometown.

The many challenges over the past couple of years (COVID, fires, etc.) have demonstrated the need to decrease dependence on our Tasting Room traffic for future DTC sales growth. The Roadshow Events channel is a great way to do so.

HOW
Before you pack your bags and head out on the road, here are a few things to consider.

  1. Define your objective. Are you seeking to engage and retain existing Wine Club Members? Are you hoping to grow the Wine Club? Are you hoping to sell more wine from your existing mailing list? Are you trying to grow your mailing list?
  2. Then, measure what matters. The WISE Triple Score (Orders, Club, Data) applies here just as it does in any other DTC channel. By keeping a balanced scorecard, you can make more data driven decisions in the future.
  3. Consider WHY we should be doing Roadshow Events, and how it fits in to the overall strategy. Then, we can intentionally build a program set up for future success.

Clarifying our intent will then influence our Roadshow Event goals, which in turn will drive our Roadshow Event type decisions, go to market strategies, planning and execution, and how we will measure our Roadshow Event success.

https://wineindustrysaleseducation.com/taking-it-to-the-streets/

In Winery DTC, We Are at the End of a Very Long Relay Race

US’ Shamier Little passes on the baton to Bryce Deadmon in the mixed 4x400m relay heat at the Paris 2024 Olympic Games. Photo: Jewel Samad/AFP It began years ago, and every day, we have the chance to cross the finish line strong. How we got here is not by accident; rather, it is the result of vision, dedication, and a lot of blood, sweat, and tears.

It started years ago with a vision of a brand. The starting gun may have shot off generations ago, or perhaps it was more recent. Someone somewhere had the idea to set down roots and create a brand. Significant investment was made in the vineyard sources, the winery and production facility, and of course, in the tasting room.

The vineyard crew has one of the hardest jobs in our industry. From being outside in the early pre-dawn hours in the cold to working in soaring temperatures during the heat of harvest, these crews show up and are rarely recognized. They face spiders, snakes, and yellow jackets that want to leave a mark. They work hard in these conditions to grow us the best possible wines.

The next leg of the relay baton is passed on to the cellar crew during harvest, where 12 to 18-hour days are the norm, and six or seven-day work weeks happen. It is a physically demanding job, climbing in tanks (where the gases can kill a person!), dragging hoses and pumps, moving barrels, and being around caustic chemicals all day.

The baton takes a route through the production team that stresses about getting labels through approvals and printed in time, navigating the market to get glass and corks, and getting the wine ready for bottling. It is carefully choreographed with a mind towards budget, a balancing act to be sure!

Finally, that baton is passed to DTC. Many very talented people tried out and did not make the team. You are here today, representing those who worked so hard to get the baton to you. In DTC, we are the face of that vision, that vineyard work, and the cellar and production teams. We owe it to them to finish strong, to hit the goal: The WISE Triple Score. Are we asking every guest to buy wine, to join our club, and to keep in touch via our mailing list?

Now, the spotlight is on DTC. The whole world is watching how we perform. The team behind us has done their jobs. Let’s finish strong for them.

What are you doing to train for the Winery DTC Olympics?

Mystery Shopping Debrief

One of the most anticipated parts of several WISE courses is the opportunity for attendees to go out and Mystery Shop their direct competitors. It is a very structured approach to looking at the experience, with a formal debrief. It is always fascinating to see how industry professionals at all levels – from frontline staff to managers, executives, and owners – experience other tasting rooms. The insights gained during this process spark actionable conversations and often change attendees’ behaviors.

During one such debrief, we found that at the wineries the attendees visited, the wine club was not verbally mentioned even once. The attendees were asked to buy wine just ONE time, with a generic ask of, “Would you like to take anything home with you today?” which can be easily dismissed with a “Nah…not today.” None of the wineries asked any of the guests if they wanted to keep in touch and join the mailing list. Combined, this is the WISE Triple Score, and the results were unsettling.

Is it any wonder that the headlines are shocking about winery DTC slowing down when we are not making the most of every guest interaction?

The conversation quickly turned to understanding WHY frontline staff perform, or don’t perform, up to standards. The group discussed three primary reasons staff does not ask for the order, warmly invite guests to join the wine club, and ask to keep in touch.

1. Imposter Syndrome: Have you ever had that metallic taste in the back of your throat, the adrenaline rush, when a sale starts to add up? Perhaps it started with a case, then grew to two, and suddenly the sale is more than your rent, and then more than you earn in a month? Perhaps the thoughts going through your head are, “Wow, this is more than I have in my bank account right now,” or “I really hope their credit card goes through because mine would not!” How can we possibly be equals with that guest when they spend more on wine than we spend on rent?

– The answer lies in the Platinum Rule – sell to their wallets, NOT yours! Do unto them as they want done. That guest is at a different point in their life; they have a different spending capacity than we might have. They want to be here, and they want to buy wine. We are here to help them figure out what they want and facilitate the sale.

2. Fear of Rejection: How can I get rejected if I don’t even ask? Or, if the guest wants to buy, they will, so I don’t need to ask. Michael Scott, quoting The Great One, said it best. We miss 100% of the shots we don’t take.

– The fastest way to increase Tasting Room sales is to ask every guest if they would like to take SOME (subjective) of . Why SOME? It means a different volume to everyone, just like our wallets are different. “Some” may mean a few bottles, a case, or a pallet. When we ask if they want to take “a couple of bottles,” we are restricting the sale. Let the guest guide the sale and keep it open-ended.

3. Lack of Professional Selling Skills: Look, hiring for hospitality heart is key – no one can train for that. Either the candidate is born with it or not. It is a priority when hiring. That means it is up to us as managers to develop our team’s professional selling skills through clear expectations, constant gentle coaching, and sharing of key metrics. Business is a team sport, so let’s share in the successes and opportunities with our team by posting metrics. When teammates know what to focus on (sales, club acquisition, data capture), and that you are inspecting those metrics, they will respect the metrics.

There are benchmarking services and reports to monitor how we are doing. If you need insight into WHY things are not happening, we can help with Mystery Shopping or even just brainstorm. Give us a call; we are always here to help!

https://wineindustrysaleseducation.com/mystery-shopping-debrief/

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 Email 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

List of Locations