DTC Past, Present, and Future: An Interview with Lesley Berglund, CO-Founder and CEO of WISE Academy
05.07.2019  |  by The Copper Peak Team

Lesley Berglund is the Founder and CEO of ACT Coaching, which coaches wineries on change management, as well as Co-Founder and Chairwoman of WISE Academy. A third-generation Napa Valley native as well as a serial entrepreneur, Lesley has been at the forefront of selling wine DTC for decades. For our most recent Expert Series interview, our team sat down to talk with her about the elements of successful DTC, leadership, and more.

[You can also check out our most recent past interviews.]

CPL: So glad to speak with you today, Lesley. You’ve certainly worn many hats over the years. Can you tell our readers a little bit about what you are up to nowadays with WISE?

Lesley: Certainly. We offer core courses, certification courses, and workshops focused on winery DTC and leadership development, as well as mystery shopper services and on-site coaching services. We offer classes in Northern California, Central Coast, Oregon, and Washington, as well as Idaho, Tennessee and Virginia. Over all, we offer over 15 different certification programs.

The goal of all of these classes is to create leaders in the DTC wine space. The people who take these classes range from frontline staff, to DTC managers (tasting room, wine club, digital and events managers), to winery executives and owners—there’s a mix of offerings. And there is a lot of cross-functional learning and collaboration that occurs.

All together, our trainings, workshops, and other services truly do change how people approach DTC. It switches their thinking from the merely transactional to taking a more strategic approach.

CPL: As I understand it, you recently returned from Cape Town South Africa, where you were partaking in a global leadership event. Are you thinking of extending your classes more widely, outside the world of wine?

Lesley: On the contrary. Our focus is on growing the next generation of leadership in the wine industry and we study best practices around the world, and from different industries, to do so.

CPL: And what about the mystery shopper services you mentioned? How do those fit in?

Lesley: Yes, I think they are just as important as the classes themselves.

First, we make mystery shopping a part of our training. Students go into the field as an exercise, becoming mystery shoppers. The data they collect then are used to drive home lessons back in the classroom. It’s a great experience that reinforces what is, and is not, being done at wineries from a training perspective.

We also offer this as a separate service. (And I have to pause here to credit Juli Barron, who is now Direct Marketing Manager at Opus One, for suggesting mystery shopping as a service to us while at one of her former wineries.) We’ve found that the more focused a winery is on raising the bar on their guest experience, the more likely it is to retain our mystery shopper service. WISE has 80 mystery shoppers who together have done over 5,000 mystery shops in the last few years!

The goal of all of our mystery shopper services is to compile data that will open doors for wineries and help them increase their customer retention. Many times this will also lead to onsite coaching, where we help educate staff on the fundamentals of guest experience design, guest journey mapping, and customized content for wineries.

CPL: And you are working on some other services as well, right?

Lesley: Yes. We help wineries develop training manuals for onboarding new employees. We offer recruiting and organizational development support, as well as guidance in DTC and executive incentive compensation design. We are also adding the WISE Cabinet, leadership forums for winery executives and rising stars.

CPL: That’s quite a lot! So how did you get into training leaders in the wine industry, of all things?

Lesley: Well, wine is in my blood. My family came to Napa Valley in the mid 1800s. They were in the hay and feed business, and eventually evolved into the John Deere and Caterpillar Tractor dealerships. But the real change happened in the ’70s, when our first vineyards were planted by Brother Timothy [N.B. Anthony George Diener] from Christian Brothers. At 12 years old I was helping out by working in our vineyards and scrubbing the cellar for the neighboring winery, Joseph Phelps.

CPL: Sounds like you started young! So how did you end up on the business end of things, as opposed to, say, starting your own winery?

Lesley: Part of it was school. I graduated college with a BA in Economics from Wesleyan University, and then went on to get an MBA from Harvard Business School. In 1991, I co-founded the Ambrosia wine catalog business, which allowed me to develop one of the first direct marketing channels for the wine industry. The big challenge at the time was getting consumers to trust the DTC supply chain that went from the winery to final mile delivery. Very few wineries or retailers were selling wine that way back then.

I hadn’t originally planned on sharing what we learned with others. But soon other vintners—Phelps, Chappellet, Clos Du Val, etc.—wanted to start their own and get in on the success. I saw a need, and it was a strong need, so we started expanding what we did. Since then, I’ve started the equivalent of eight separate businesses throughout my wine career.

CPL: So tell me about that first business.

Lesley: The Ambrosia Wine Catalogue was DTC sales through mailing lists. We handled the database and the shipping. For the first five or six years, we tried to outsource fulfillment, but there wasn’t really anyone at the time that did it, other than Wrap-It Transit or Cartons & Crates. So, although it wasn’t my main goal, we eventually morphed into a shipping company, not only doing our own fulfillment but fulfillment for others as well.

Through the mid-1990s, we ended up launching more than 50 wine clubs for different wineries. Then the very first eCommerce sites started popping up, and I could see that this was going to be huge. So, starting in 1998, we really began to double-down on technology. We launched the first website for the catalog, Ambrosiawine.com, in 1999. From there we ended up launching another 150 winery e-commerce sites, including winetasting.com. What we take for granted today was really trail-blazing for the wine industry and DTC sales at the time.

CPL: DTC, especially digital sales, look different now, correct? [For background, readers might want to see our historical piece on flash sales, for example. — DD.]

Lesley: Yes. Things change, and you can only succeed if you manage to change with them.

In this case, change came with the bursting of the “dot-com bubble” around 2001. This is what prompted me to get involved more holistically with our winery clients with all of their DTC channels. We created an integrated eCommerce wine company, which was later sold to 1-800-Flowers.

That experience is what served as the catalyst for WISE. I took a sabbatical after selling that company, but during that time off I had continual calls from vintners all with the same problem – looking for people with the skill set to tackle the next generation of sales techniques and technology. Again, there was an obvious need out there.

CPL: So WISE arose out of a need to find people who knew the technology better?

Lesley: Well, almost all of the calls I got were from wineries where they had a good employee in place handling one or more of their DTC channels . . . but that employee just wasn’t able to take them to the next level. These wineries needed to top-grade their DTC leadership positions, but the talent pool was pretty small and they hadn’t developed that leadership internally.

So, after a few years of hard work, we were able to open WISE in April of 2009. That was 10 years ago, and it’s been an amazing journey.

CPL: So, you’re a coach, obviously. You know the value of getting help from others. Who helped you along the way? Who were your mentors? Who inspired you?

Lesley: George Schofield, former CFO of Mondavi in the 1980s, was my first mentor in the wine industry. We collaborated on a project for my Harvard Business School degree, on how to sell a collection of Aged Cabernet Sauvignon through a consumer direct channel that did not exist at the time. That project was what jump-started the creation of that first Ambrosia catalog I mentioned.

There are plenty of places I go for inspiration and information, too. I have benefited greatly from being a member of YPO (Young Presidents Organization) and especially my YPO leadership forum, which meets monthly and acts as my personal board of advisors.  I owe a lot of my career success to my YPO forum. That is one reason why we launched the WISE Cabinet program, so other industry leaders can benefit as I have. I also enjoy leadership books. I’ve gotten a lot out of reading Simon Sinek, Patrick Lencioni, and Chip Conley in particular.

CPL: So let’s shift things a bit, from your background to what you see going on in the industry today. Is there anything that surprises you?

Lesley: Really, it’s the role that DTC has played, particularly the five pillars we cover in our classes. If someone can master the multi-channel leadership execution in the tasting room experience, digital engagement, event planning, and wine club and phone sales, then you have someone who can become ready to be a winery GM, President or CEO. When we started, there were almost no winery GMs or president who had come up through the DTC career path.  We are out to change all of that.

Having a multi-channel DTC expert at the helm really can take your winery to new heights. Since DTC is the main breadwinner for most wineries, it makes sense that you need to have true DTC professionals in place at the higher levels of the organization.

CPL: That’s interesting, because it seems like everyone is attempting to create and deliver exceptional experiences, whether in the tasting room, online, or through event services at the winery. But if that’s the case, they need to do more to differentiate themselves in these channels, correct? So that they don’t get lost in the shuffle of everyone doing the same things?

Lesley: So, Napa is in the middle of a bout of one-upmanship as wineries try to top each other by creating the next great winery experience. Putting aside the fact that this may be changing who can afford to come to Napa in the future, this trend is actually a good thing, as it keeps the industry trying new things and diversifying. Different generations want different experiences, and the stats prove this out: A winery can’t just get away with the cattle-call of the walk-in tasting room anymore. The experiences have to be unique, creating an emotional connection with the brand.

But there is a downside, too: Because traffic is up, people are going to fewer wineries each trip, because these experiences take longer. People are lingering. So every winery has to work to be one of the stops people don’t want to miss.

CPL: So what about the future, then? Where is DTC going from here?

Lesley: The dance gets faster—consumer expectations continue to evolve, wineries learn how to be more successful, and thus the competition gets tighter. Wineries need to constantly change and adapt to be proactive and strategic, and from a much more critical point of view.

It’s still the case that tasting rooms are the best way to build a solid foundation for DTC sales. But wineries still need to improve on many fronts. Capturing customer data, for example. When wineries don’t make specific plans to do this—when it’s not a focus—we find that they only capture key customer data less than 10% of the time. When they learn how to do this and make it a focus, they successfully capture data 65% of the time.

It’s like that old saying: “Sometimes we are victims of our own success. What would happen if we really tried, as if our business depended on it?” Because the time always comes when the business does depend on it. If you wait until there is a problem, like your sales dropping off for the second quarter in a row…well, by then it’s too late.

CPL: Great stuff, Lesley. I have one last substantial question, and it just has to do with the times we live in. You’ve been deeply involved in this industry for decades. As a top leading woman in our industry, have you faced any challenges as a result of being a woman? How is the atmosphere for women now, in 2019?

Lesley: Honestly, I don’t think I’ve ever slowed down enough to notice any challenges due to my gender! But I can say a few things about where we are here in 2019.

On the one hand, some great women truly are leading the way today. The first generation of WISE supporters proves how highly focused and driven these women leaders are—people like Lesley Russell, Angelica de Vere Mabray, and Liz Mercer. They really are changing the industry, and for the better.

Unfortunately, there is still an imbalance at the very top. There are not many women presidents and CEOs in the wine space, and this needs to change. For my part, I’m proud to help support and grow future leaders, no matter who they are, but I’m particularly proud of these successful women.


Based on Lesley’s insights and discussion, here are 10 takeaways about leadership and growth in the wine industry:

  1. Even if you have a great manager (or managers) in charge of your tasting room, digital marketing, wine club, and/or events, that doesn’t mean that he or she is ready to take the business to the next level. Train and develop them!
  2. Indeed, it is important to have an understanding of all aspects of DTC at the highest levels of leadership.
  3. DTC fuels growth best when one considers all DTC channels (tasting room, eCommerce, digital engagement, wine clubs, events, phone sales etc.) and when one takes a strategic, rather than transactional, approach.
  4. The nature of DTC changes with the times, and successful wineries learn to change with them, too.
  5. Every leader needs a mentor (or several). Seek them out. Collaborate with them, if you can.
  6. Reading and participating in professional networks, too, can provide ideas and inspiration. Dedicate some time every month to these activities.
  7. Creating exceptional experiences is no longer exceptional—everyone is doing it. It’s the minimum bar for entry. This means that wineries have to work harder to create the experience that people want to have.
  8. This drive toward experience also means that people are visiting fewer wineries per trip, lingering longer at each one to get the full experience. The data are bearing this out clearly.
  9. To continue to grow, wineries can’t just rest on current success. They need to collect data and proactively target their markets. The time to do this is now, not when a problem shows up on the bottom line.
  10. There is opportunity for everyone in this industry. But only those with focus and drive will succeed. And even then, mentorship and training will be the keys to unlocking that success.

We here at Copper Peak also believe in people, and we make a point of training and promoting from within. Many of our staff have been with us for years, even decades, and they know the business inside and out.

If you’d like to have your winery work with our people to improve your wine shipping and logistics, feel free to give us a call or use Copper Peak’s contact form.