VineSpring Team Spotlight: Leslie Osborne

We felt like we hit the jackpot when Leslie Osborne joined the team. Leslie is VineSpring’s Head of Product. Not only does she have decades of experience in software product management, but she is also immersed in the wine industry and has the certificates to prove it. Combining her hard earned experience in product management with her love of wine is a dream come true for Leslie. We interviewed her to give you a clear picture of the people and passion behind VineSpring. Plus, we wanted to hear her advice on how wineries and breweries can use technology to build a successful DTC channel and a strong following.  


What initially attracted you to the wine industry?

Leslie Osborne, Head of Product VineSpring

To me, wine represents an endless learning opportunity. There’s always a new country, a new region, a new grape, etc. to explore. Naturally, as part of that process, I also became curious about the winemaking process and the business behind it all. I enjoyed listening to winery teams and hearing the challenges they faced and thought, “I want to help this industry evolve. I want to help craft its future.”

You have several wine certifications, can you tell us what you studied and where?

I’ve earned a variety of wine-related certifications over the years. I specifically got my WSET Level 1 Certification from the Napa Valley Wine Academy, as well as my Italian Wine Professional certification. I also received a similar Level 1 certification from the International Wine and Spirits Guild and a certificate in Wine Business Management from Sonoma State.  All of these courses have helped give words, structure, and context to the experiences I’ve had tasting wines and visiting wineries. I don’t think you have to know anything about wine to enjoy it, fortunately, but being able to nerd out on it a little bit makes me happy.

What does your role as the Head of Product at VineSpring involve?

If you boil my role down to its primary elements, it’s all about decision making, prioritization, and embracing the associated responsibility, as it relates to our product suite. I also care a lot about how work is done, so add in some interest in efficient processes for good measure. What that all translates to is helping to define the company vision—and in combination with understanding the competitive landscape and market needs— being able to distill everything into an actionable product roadmap.  From there, and speaking more on day-to-day terms, I help define and ensure that we’re taking on the right work at the right time as a product development team.

What did you want to be when you grew up?

I wanted to be a businesswoman. Power suit. Boardroom. Corner office. Quite a dream, eh? Slightly more specifically, I was very into International Business and cars (I was an unusual kid), and really wanted to be a businesswoman working for BMW in Germany. That never quite panned out, but I think it’s for the best.


What do you like best about mixing your wine background and your technical background?  

Don’t they say that luck is when preparation meets opportunity? I feel very lucky to take the 20+ years of experience I have in software Product Management and use that to help a new (to me) industry innovate and evolve. There’s so much technical opportunity here. It’s work that doesn’t feel like work.  

What advice would you give to a winery or brewery that wants to launch a DTC eCommerce channel?

Don’t half-ass it. It’s going to be an important part of your business—consider it an investment in your future success—so prepare, research, plan, and find the right vendor (or vendors) who will partner with you to help you reach your goals.


Technology seems to advance in the blink of an eye. What sticks out to you as a technology that will change the way that wineries and breweries do eCommerce?

At the company I worked for previously, we used Machine Learning (ML) in some pretty slick ways to analyze data to ultimately enhance our product sales. I think ML could be applied in similar ways in wine DTC to dynamically craft and present the right offerings to customers at the right time. ML requires investment, though—in terms of brain power, computing power, etc—so I hope the industry will be willing to take that leap.

What stuck out to you most in the recent 2019 SVB Industry Report? How do you suggest a winery or brewery update their strategy to counterbalance the predicted oncoming drop in demand?

There’s continued talk about needing to offer different products in different packaging in different ways to keep wine “current” for certain sectors of the market. I don’t have any answers to offer, but I feel like that’s short-sighted, impractical, desperate advice. I do feel it’s valuable for wineries to be run like any other business, where you need to know your market, your customer, and use data to plan and execute efficiently. Those fundamentals never go out of style.

We talk a lot about perfecting the customer experience in the industry. What is one way that you think wineries and breweries can improve the customer’s experience online?

Bring as much of yourself to the online experience as you can and make us, the consumer, feel included. Every winery, winemaker, team, location, etc. has a story, a personality, a feeling. Those elements help form a connection between the consumer and your wine, and your specific combination of those things makes that connection with you unique. People will certainly buy your wine because it’s tasty, and a lot of wineries make tasty wine, but consumers will keep coming back because of YOU.

Most of us don’t live in wine country and it takes a lot of money and time to visit. If your online experience (website, social media, marketing outreach, etc.) can help us continue to feel connected to you, we will probably keep buying your wine (and coming to visit periodically :-).

What do you think sets VineSpring apart from the other options out there?

VineSpring is very much all about providing paths to success. Note my use of the plural there.  While we provide an allocation and club management solution, our platform enables innumerable others. You can use what we offer and/or craft connections from our platform to your preferred software tools to create your own solution ecosystem. One size doesn’t always fit all!

Are you part of a wine club What got you hooked on that winery and keeps you coming back for more?

I’m a club member of Peter Franus Wine Company. I was introduced to Peter Franus’ wines at a wine dinner in Denver many years ago. I had a lovely chat that evening with Peter’s wife, Deanne—we both have Midwestern roots, so we hit it off—and was surprised by the fact that I enjoyed every single wine they presented.


How do you keep up to date on industry news? Do you have a favorite publication or blog?

I love the Daily News Email from Wine Business Monthly. I’ve been receiving that email for several years. It’s concise, easy to read/scan, and does a good job of hitting the industry highlights. That and a cup of coffee is pretty much how I start each day.  

What is your favorite tasting room experience and why?

My favorite experiences are the informal ones, where you get a chance to sit down with the winemaker or winery staff member and just have a conversation. If that includes a stroll through the vineyard to discuss fine points of caring for the vines, trying something fresh out of a tank or barrel to understand the effects of steel and oak on aging, or some other glimpse into “a day in the life of,” all the better.

What wine or beer do you plan on bringing to your next dinner party

The next dinner party I’m attending has a “Spain vs. France” (food/wine) theme. Since I don’t have much Spanish wine (yet!) in my cellar, I’ll probably bring some Bordeaux (left bank is where it’s at!) and Champagne. Beyond that, I try to bring whatever best suits the group. Wine nerds? Bring an interesting grape from an unusual place. Label snobs? Bring a brand name everyone knows. New to wine? Bring a solid example from an accessible location. Just an everyday gathering of good friends? Bring whatever I’m most excited to share and drink that day.


Do you want to hear more of Leslie’s thoughts on DTC wine? Read The Future of Technology and Allocations and The Beverage Alcohol Industry’s Many Reinvented Wheels.





Chris Towt