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 recruited for a full-time job in aviation, working for a fixed based operator (FBO) in Saint-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. In a predominately 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.
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 two-and-a-half 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 as a leader?
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 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.
READ: BMO says Canadian economy expected to see modest growth in 2026 amid trade uncertainty
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 also 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?
Having different perspectives is always good. We wouldn’t be able to improve and grow if everyone did everything the same. 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 lessons would you 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 walks the talk, having received the Women of Inspiration Authentic Leader Award in 2022.)
What are some key traits leaders today should possess?
Adaptability is more important than ever. Whether that’s adaptability to the market volatility or to changes in workforce expectations. We live in unpredictable times and leaders need to learn to roll with the punches and adapt quickly. Also, information is power. The more data and information leaders have, the better they can steer companies in the right direction and make appropriate decisions for the future.
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.
READ: The future of work—according to generation Z—is purposeful, digital and flexible
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.
What do you hope to accomplish in your current role?
I hope to set this award-winning winery up for lasting success! Putting the right people in the right positions and empowering my team to challenge the status quo is key. I hope to inspire, empower and positively impact my team to be game changers in this industry.
This interview has been edited for length and clarity.
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 article was first published in Canadian Grocer's December 2025/January 2026 issue.
