Growing up, Vaikla immersed herself in nearly every corner of the Estonian community—spending summers at Jõekääru as both a camper and counsellor, training and competing with Kalev Gymnastics, and taking part in Hellakesed and Gaidid. In high school, she also joined the Lastekoor (children’s choir) and had the opportunity to sing at Laulupidu (the Estonian national song festival). “It was unforgettable,” she says, “just being up on the stage with several thousand other singers. But when it came time to exit the stage, it was pure chaos. At one point the skirt of my rahvariided (folk costume) got caught between two people moving in the opposite direction and we were all panicking,” she laughed. “But that moment gave me an appreciation for the sheer scale and energy of those events.”
As a student at Western University, Vaikla also spent a few summers working at the Tartu College office and in Toronto’s Estonian archives at VEMU. More recently, she is also a member of Korp! Amicitia and has organized the annual AK parties. “I liked doing that because it brings a whole bunch of Estonians together. We had a really great turnout last year,” she said.
“… growing up with so many activities forced me to manage my time well and juggle multiple priorities, which translates directly into my career, where I thrive on balancing responsibilities and day-to-day variety.”
(Kairi Vaikla)
Looking back, Vaikla says these experiences were instrumental in shaping both her worldview and her career. “Doing sports and being active taught me perseverance—training, competing at high levels, working through injuries—all of that developed my work ethic and helped me see failures as learning experiences. Second, the network of friendships I built in the Estonian community was hugely influential. Being surrounded by driven, supportive people has been a lasting source of inspiration and fun. Finally, growing up with so many activities forced me to manage my time well and juggle multiple priorities, which translates directly into my career, where I thrive on balancing responsibilities and day-to-day variety.”
Vaikla is now Head of Product Management at Inbenta, an AI-based software company specializing in developing virtual assistants for businesses. “We provide the AI engine that makes sure the conversations you’re having with those assistants aren’t completely robotic, so it feels like you’re actually talking to a human,” she said. Vaikla leads a team of four project managers across Europe, Brazil, and Canada, researching and driving the product strategy to stay competitive.
“No two days are the same,” she said. “One day can involve testing product features to make sure they meet our standards, collaborating with marketing to ensure we’re telling the right story, supporting our legal team with contracts, joining sales calls, supporting the sales team, or doing customer demos to hear feedback directly. But that’s something I love about my role!”
The Technology & Services Industry Association (TSIA) has named Inbenta the 2025 Digital Customer Success Innovator of the Year!
“If I could, I’d still spend my whole summer at camp with my friends. I always look forward to the Jõekääru alumni camp. It’s a great way to get together with friends and reminisce.”
(Kairi Vaikla)
Today, Vaikla stays active in the community when she can. “I was very involved as a child, but life has gotten busier as I’ve grown older. If I could, I’d still spend my whole summer at camp with my friends. I always look forward to the Jõekääru alumni camp. It’s a great way to get together with friends and reminisce.”
Watch Kairi Vaikla’s Community Unwrapped episode to hear more about her career, insights on succeeding as a woman in a traditionally male-dominated field, and advice for breaking into product management.
Explore eestielu.ca to see more Community Unwrapped episodes and stay connected with your community.
This article was written by Natalie Jenkins as part of the Local Journalist Initiative.
