Fion Lee-Madan, a graduate of the Catalyst’s RBC FinSec Incubator, is an experienced technical and business leader specializing in B2B enterprise software and AI. She has a track record of driving product-market fit and customer success for Fortune 500 companies and ATG through its Oracle acquisition.
With degrees from the University of Toronto and Boston University, she now leads Fairly’s AI roll-out. Having lived and worked internationally for 20 years, she is committed to responsible AI and mobilizing a global network to uphold Fairly AI’s standards.
Balancing motherhood and ambition
Between the first and second chapters of her career, Fion Lee-Madan stepped back to focus on being a stay-at-home mom. One day, her five-year-old daughter came to her and said, “Mom, when I grow up, I want to be my brother’s assistant, bring him coffee and tea.”
The words stopped Fion in her tracks. “Is that how you see your mother?” she wondered. She realized she wanted to model something different for her daughter — an example of leadership, ambition, and independence. And so, she stepped back into the professional world, determined to make an impact.
A year later, Fion’s daughter had a different complaint. “Mom, you’re like the stepmother in Cinderella, always ignoring me.” By then, Fion had become a startup founder, and the reality of balancing work and motherhood hit hard. “You can’t win the whole inequality thing,” she says. “It was just the beginning of mom guilt.”
Letting go of mom guilt
For many women, career success comes with a side of guilt, and Fion was no exception. An article on ‘mom guilt’ changed her perception, reinforcing that a mother’s instinct to worry is natural but not always necessary. Though her husband was the stay-at-home parent, she still felt trapped in a mental loop of worry — reminding him about doctor appointments, school tasks, and daily routines. She had to learn to let go. “Eventually, I told myself: If I don’t remind him, it’s okay. He’ll figure it out next time.”
It was a pivotal shift. Once she let go of unnecessary worries, she freed up mental space for herself, her work, and her ambitions. “A strong support system — whether from a partner, family, or hired help — is essential for a female founder with children,” she says.
Building a career in tech
Fion is a lifelong learner who thrives in competitive markets. In the first chapter of her career, she spent over 20 years leading technology teams in emerging digital fields. Now, in her second chapter, she is the Technical Co-Founder, COO, and Strategic Partnerships lead at Fairly AI — an AI governance platform ensuring organizations deploy AI responsibly.
The pandemic marked a major turning point. With schools closed, Fion saw firsthand how essential they were — not just for education, but for childcare. “The actual teaching time in an eight-hour day is probably max two hours, but the child-minding is critical,” she notes. Like many parents, she faced the challenge of keeping her kids engaged. “Do I feel guilty about not doing arts and crafts? That was never my thing, so no, I actually don’t.”
Even now, with her children older, she makes time on Friday evenings for them — but ironically, they often prefer video games or hanging with friends. “Honestly, I have no regrets,” she says with a laugh, “but sometimes I wonder — because I was so busy then, are they ignoring me now?”
Addressing gender gaps in tech
In addition to raising her teens, Fion mentors Grade 11 students in Markham and reviews co-op applications for the University of Waterloo’s Computer Science program. Recently, after reviewing 93 applications, she realized she had unknowingly selected 11 male candidates. It made her pause.
“What strengths did the boys have that the girls didn’t?” she asked herself. Reflecting on her own education, she saw a trend: many girls excel in academics but don’t always participate in competitive programming or hackathons, which are critical for standing out in tech. “There are now hackathons designed specifically for girls,” she says. “It’s a step in the right direction, but the gap still exists.”
Fion’s own schooling was empowering. She attended an all-girls school in Hong Kong until Grade 6, where there was never a question of whether girls were good at science or math. “When I came to Canada and entered a co-ed classroom, I was shocked that girls were made to feel like they weren’t naturally good at STEM. That was a new concept to me.” Ironically, today, her daughter is more interested in programming than her son — “She loves to be a hacker.”
Redefining success: letting go of control
As a startup founder, Fion knows that entrepreneurship has its ups and downs. The key, she’s learned, is choosing the right people to go on the journey with — whether co-founders or team members.
Her perspective shifted when she read The Happiness Hypothesis: Finding Modern Truth in Ancient Wisdom by Jonathan Haidt. “All my life, I’ve been setting goals. But the startup world has taught me that no matter how much you plan, there are infinite factors beyond your control.”
The idea that happiness isn’t tied to a single destination changed how she approaches both work and life. Referencing the famous “Startup Curve” from Y-Combinator, a prestigious startup accelerator based in Silicon Valley, Fion says that maximizing happiness is harder than maximizing time to last long enough to find your product-market fit. Fion mentions that according to Forbes, 72% of founders report that entrepreneurship has affected their mental health. “Still, most founders say they’d do it again.”
Shaping the future of AI
While the fight for gender equality in tech continues, Fion has found her own balance — by redefining success, letting go of guilt, and focusing on what she can control. In the ever-evolving world of AI, she’s determined to shape the future, not just for herself, but for the next generation of women in tech.
