The Leaders: Lessons from Annemarie Heikenwälder, managing director, Pelee Island Winery
What is your leadership story?
I was born in Austria but moved to Quebec when I was eight. My parents were pioneers in organic farming in Austria and later bought a farm close to Montreal, so I grew up with this mentality of being close to nature. My parents would have liked me to follow in their footsteps, but I wasn’t interested in farming and was determined to follow my own path. After completing an Honours Bachelor of Commerce degree from the University of Ottawa, I was immediately recruited for a full-time job in aviation, working for a fixed based operator (FBO) in St. Hubert, Que. There I quickly made a name for myself, moving on to lead aircraft sales and becoming head of sales and marketing for Diamond Aircraft. (Heikenwälder was recruited to aircraft sales after being named among the “Top 20 under 40” in Wings Magazine in 2017 for raising the FBO’s occupancy from 40% to 100%.) Professional development is important to me too. I earned an IATA Aviation Management certificate from Stanford University.
Working in a predominantly male environment, I worked with associations and boards to raise the profile of women in aviation. We encouraged university programs to attract more females to the industry, and I’ve always supported female pilots. I certainly broke some glass ceilings during my 15 years in aviation, but I was also lucky to be surrounded by mentors and others who supported me along the way. (Today Heikenwälder is the only woman in Canada running a winery the size of Pelee Island Winery.)
How did you get your start in the wine business?
In my previous role I was travelling a lot and home only one week a month if that. My territory was pretty much the world for some aircraft models. I decided it was time for something that could ground me a little more and the opportunity came up at Pelee Island Winery. I took away a lot of discipline working in a highly regulated environment like aviation, which translates well to the regulated world of winemaking where I’ve now been for 2.5 years.
What is your leadership philosophy?
I approach everything collaboratively but also give my crew the rope they need to get things done. When issues pop up, I make sure the right people are in the room to discuss the solution together. It’s never a one-man show.
When I have an important decision to make, I also listen to my gut always—it has never veered me in the wrong direction.
How did you handle a difficult decision in a leadership role?
When the world shut down during COVID-19, we had to make some very challenging decisions in aviation, particularly around staffing. I needed to let people go but also bring back teams in a safe way during the recovery period. In that time, I learned that it’s very possible to scale down your teams to operate more effectively, but you have to continue to grow and build them up again when volumes resume. When I got to the winery, there was a lack of structure and accountability in certain roles, which required me to restructure certain departments. But it also allowed me to put the right people in the right places, which has set the business up for future success. I know if I was hit by a bus tomorrow, the business could run without me for a time, and that’s a very powerful thing. I really believe with the right people in place, a business will run like a well-oiled machine and that is key to a company’s long-term success.
What is the biggest challenge facing leaders today?
I think a major challenge today is the uncertainty of changing market conditions which creates a real test in agility and navigating these changes. Tariffs are the most recent example, but there have been countless other [events] in the last five to 10 years where markets have changed nearly overnight and leaders have had to make tough decisions on redirecting their businesses to remain resilient.
Tell us how you've led the business through change, specifically the introduction of beverage alcohol in the convenience channel?
It was an interesting time to get into the wine industry because it turned upside down the moment I joined. I think coming in fresh from another sector entirely was an advantage because I wasn’t stuck on how things used to be done. I’ve always thrived on change and in this case, we leveraged our sales team and their vast experience to guide us through this change. We were already in grocery stores, so opening up the convenience side was a huge opportunity. Putting people in the right places has helped us make strides and we’ll continue to do so by pitching new product opportunities in this space.
Being in an industry that’s quite culturally diverse, how do you lead across global markets?
My background on the international sales and marketing side has been an asset for us here at the winery. When you speak a common language, it enables you to relate to one another and build relationships. I am fluent in four languages and speak seven conversationally—and I’m now learning Arabic too. Not only was I forced to learn a new language when I came to Montreal, but growing up, I went on a lot of trips to learn languages. At 13, I presented a business plan to my parents, convincing them to let me study in Mexico City and stay with a host family, which I did the following year. You gain such a deep understanding of a culture when you’re immersed in it like that. To this day, Mexico is very close to my heart.
How do you handle conflict or differing perspectives among your team members?
I think having different perspectives is always good. We wouldn’t be able to improve and grow if everyone did everything the same way. When there is a conflict, I bring everyone involved together, really listen to all their perspectives and collaboratively, we devise the best path forward. Sometimes you walk in expecting one direction but leave heading 180 degrees the other way—and it’s an even better route.
There’s obviously some compromise involved but we ensure it’s a win-win situation for everybody. I think people are more at ease when they’re able to voice their opinions. We also try to do things differently next time we face a similar situation so we’re not dealing with the same issue 16 times over.
What are lessons you’d share with other aspiring leaders?
Be genuine. When you stay authentic and true to yourself, it encourages others to do the same, helping everyone to bring out their best. (Heikenwälder practices what she preaches, having received the Women of Inspiration Authentic Leader Award in 2022.)
What’s a piece of advice you’re glad you ignored in your career?
Being told I wasn’t old enough to go for certain roles. My age has come up several times in my career as a hindrance to pursuing new opportunities, even though the experience and competence was there. So, I’m glad I kept pushing forward.
How do you stay inspired in your current role?
What’s exciting about this job is that I’m learning every day as I get to sit down and talk to the winemakers about what they do. For all leaders, I think it’s important to take a moment to do something that makes you happy, at least once a day. In my case, I may take a trip to the island to disconnect and stroll through the vineyards to soak in what we’re doing here. Or I’ll ask the winemakers to take me around to try the latest vintage or pressed juice. If you follow this recipe, you’ll look back at your week and find it was awesome in many ways, no matter what happened.
- Fast Four
Your first job?
I loved horseback riding, so I got my first job mucking stalls for $5 cash an hour.
Biggest indulgence?
Binge-watching TV shows.
Favourite destination?
Mexico, and more recently Turkey.
Favourite hobbies?
I’m a private pilot so nothing beats the feeling of sitting in the airplane by myself and just cruising. I’m also a runner and planning a half-marathon soon.
This interview has been edited for length and clarity. It originally appeared in the November/December 2025 issue of Convenience Store News Canada.