How Successful Wineries Do Hiring, Retention, and Guest Experience Differently

Running a winery tasting room is one of the most deceptively complex jobs in hospitality. On the surface, it looks like pouring wine and telling stories. In practice, it’s managing a rotating cast of part-time staff, navigating generational shifts in how guests want to engage, and delivering a flawless experience every time, to every visitor, while keeping the business humming behind the scenes.

It’s a challenge that sits squarely at the intersection of people, process, and technology. And it’s exactly the kind of challenge that Würk and OrderPort were built to help solve.

Würk’s payroll and HR platform is purpose-built for compliance-heavy, people-first industries, helping operators pay and manage their workforce without drowning in administrative complexity. OrderPort is the wine industry’s leading ERP and point-of-sale solution, designed to make running a winery’s operations, wine club, and tasting room as seamless as possible. is the wine industry’s leading ERP and point-of-sale solution, designed to make running a winery’s operations, wine club, and tasting room as seamless as possible.

Together, the two companies share a belief that when the back-office runs smoothly, the front-of-house can shine.

We recently sat down with Lailand Oberschulte of OrderPort to talk about wine industry trends and what it really takes to build and retain a great tasting room team, from the art of finding people with natural hospitality instinct to the science of onboarding them quickly and keeping them engaged. Lailand brings a frontline perspective on how wineries are navigating hiring pressures, generational change, and the growing expectation that a visit to a tasting room isn’t just a transaction. It’s a memory.

Here’s what she had to say.

Training and Talent: It Starts With the Right People

When asked about the biggest staffing challenges wineries face, Lailand was direct: it’s not a shortage of good people. It’s a shortage of good training.

“This is a really niche market, and there can be a lot of turnover because it’s such a hospitality-centered job. It’s like being a bartender on steroids. You have to know all about wine, but also the stories of the winery and the family behind it.”

Tasting room staff need to recall detailed wine knowledge, represent the brand’s story, and connect genuinely with guests, often all at once. That combination is harder to develop than it might seem. Someone who excelled as a restaurant hostess, for example, may struggle in a tasting room setting where the guest interaction doesn’t end after seating.

“You can teach people about wine,” Lailand said, “but you can’t teach them how to be a people person.”

Wine Industry Trends: The Generational Shift

The guest experience doesn’t just vary by wine knowledge. It varies by generation, and wineries that understand this distinction are pulling ahead.

Lailand pointed to Gen Z connectivity as one of the most pressing questions facing the industry today: how do you get the next generation excited about wine when the traditional approach to wine culture feels inaccessible or off-putting?

“Pretentious and snobby approaches doesn’t work. We need to treat them with respect and make the experience fun so they feel seen and acknowledged. They don’t want technical tasting notes, it feels too complicated.”

There’s also something unique about wine compared to other hospitality verticals. Guests care deeply about provenance in a way they simply don’t in other settings. As Lailand put it, you don’t think twice about where your hotel mattress was manufactured, but people care a great deal about where their wine came from. That origin story is a feature, not a footnote, and tasting room staff need to tell it well across a wide range of audiences.

The Experience Is the Product

Perhaps the most striking insight from the conversation was how clearly Lailand articulated the relationship between experience and product in the wine business.

“If the experience is 10/10 but the wine is 7/10, people will come back. If the wine is 10/10 but the experience is 5/10, they won’t come back. A memorable tasting experience doesn’t just generate a bottle sale. It increases the likelihood of club enrollment, return visits, referrals, and long-term customer loyalty.”

Guests aren’t just evaluating what’s in the glass. They’re evaluating how the visit made them feel. That reframes the entire conversation around tasting room hiring and training. The staff aren’t just order-takers or product educators. They are, in many ways, the product itself.

Hiring and Retention: Reputation Is Everything

The competition for strong tasting room talent has intensified significantly. Job boards for these roles are extensive, and wineries are increasingly aware that how they treat their people has a direct impact on their ability to hire.

“Wineries develop reputations for how they treat people. There is an old guard that treats staff well, and people fight to get into those wineries.”

The most forward-thinking operators aren’t waiting for talent to come to them. They’re building environments worth working in, offering healthcare and 401(k) plans even to part-time workers, and creating real career pathways. Many of the industry’s best cellar managers started as barbacks. That kind of trajectory doesn’t happen by accident. It happens when operators invest in people for the long term.

How OrderPort Supports Wineries at Every Stage

All of this context shapes the way OrderPort approaches its role in the winery ecosystem. The goal, as Lailand described it, isn’t just to provide software. It’s to make sure that software never becomes a bottleneck in the training and onboarding process.

“Our goal at OrderPort is to make our system intuitive and easy to use so that, as wineries build these roles, training doesn’t consume all of their time. We aim to make it easy to train and acclimate staff so they can focus on doing their jobs.”

That commitment shows up in several ways. OrderPort provides in-system training and onboards every new winery into the platform directly. For those who want a more hands-on start, the team offers to send a representative on-site to walk through everything in person and even run the winery’s first wine club alongside them.

Beyond implementation, OrderPort offers ongoing support through:

• OrderPort University, a documentation hub where staff can access resources on their own schedule 

• Monthly Master Classes, deep-dive system reviews led by a Customer Success Manager

• Live customer support, seven days a week, so issues get resolved in real time rather than piling up

The philosophy is simple: the less time your team spends figuring out the software, the more time they spend taking care of guests.

What Lailand makes clear is that the tasting room is the heart of a winery’s brand, and the people staffing it are what make or break the experience. A great visit can sell more wine than a great vintage. That’s not a small insight, it’s a strategic imperative.

Building that kind of team requires more than good intentions. It takes competitive compensation, thoughtful benefits, and systems that get people up to speed quickly so your staff can focus on connecting with guests rather than wrestling with software.

That’s the philosophy behind both OrderPort and Würk. OrderPort gives tasting room teams the tools, training, and ongoing support they need to operate confidently from day one. Würk gives winery operators the HR and payroll infrastructure to hire compliantly, offer benefits that actually attract talent, and manage a workforce that often spans full-time, part-time, and seasonal roles simultaneously.

In an industry where reputation travels fast, where staff talk, guests share, and the best wineries have people lining up for jobs, getting the people side of your business right isn’t optional. It’s the competitive edge.

Ready to see how Würk can support your tasting room team?

Learn more about Würk’s payroll and HR solutions for wineries and other alcohol and beverage companies.