In an exclusive interview with CanadianSME Small Business Magazine, Liz Samson, Head of Industry Relations and Operations at Square Canada, shares insights on the evolving landscape for women entrepreneurs, the role of fintech in breaking down barriers, and how technology is shaping the future of small businesses. With a distinguished career spanning Wealthsimple, RBC, and now Square, Liz discusses how digital tools are enabling business owners to thrive, why mentorship and advocacy are critical for women in leadership, and what trends will define Canadian entrepreneurship in 2025.
With an impressive career spanning Wealthsimple, RBC, and now Square, Liz has been at the forefront of fintech and digital innovation, championing inclusivity and empowerment in traditionally male-dominated industries. Under her leadership, Square continues to equip small businesses—particularly women-led ventures—with the tools, resources, and financial access needed to thrive in a rapidly evolving economy.
Liz is among the most senior women leaders at Square Canada, bringing with her a wealth of experience in tech and fintech, including at Wealthsimple and RBC.
Square data shows that approximately 56% of business owners on your platform are women. What unique challenges and opportunities do you see for women entrepreneurs in Canada’s current economic landscape?
Women entrepreneurs are an undeniable force in Canada, playing a key role in driving local economic growth. Our data reveals that 75% of women-led business owners using Square say our platform empowers them to shape their own entrepreneurial journey. That’s what inspires me—seeing women take charge, expand their businesses, and strengthen the local economy.
A major challenge for small businesses in recent years has been adapting to rapid changes—whether it’s evolving consumer expectations, shifting regulations, or the growing need for frictionless digital experiences. Independent businesses, in particular, often struggle to keep pace while staying true to their brand and community roots. That challenge is also what drew me to Square and its mission of equipping entrepreneurs with tools for their businesses to grow and succeed in an increasingly digital world.
How is Square leveraging technology to help women-led businesses overcome systemic gender biases and accelerate their growth in a challenging economy?
Our data shows that nearly 80% of women entrepreneurs on Square’s platform processed card payments for the first time using our tools. That’s a major milestone, underscoring how easy-to-use, integrated solutions can empower Canadian women to run their businesses more efficiently. Whether it’s a local café owner, a multi-location restaurateur, a beauty professional, or someone in the service industry, our commitment remains the same—delivering the technology and support needed to fuel their growth.
For me and my team, the goal is clear: ensuring Canadian women—whether they’re just starting out or scaling an established business—have access to the tools, funding, and resources they need to succeed. It’s about breaking down systemic barriers that have historically made entrepreneurship more difficult for women. This means fast access to earnings, better funding opportunities, and ongoing support to help them grow on their own terms.
Based on your experiences at RBC, Wealthsimple, and now Square, what have you learned about navigating and succeeding in male-dominated tech environments?
I’ve also been fortunate to learn from incredible mentors—especially in my early years when there were even fewer women in leadership roles within the financial sector. Tech companies tend to take a different approach to problem-solving, embracing a boundless vision of what’s possible. That kind of creator’s mindset resonates with me, and I’m grateful to be part of an organization that fosters an inclusive and empowering environment for women in technology. In fact, women make up the majority of Square’s leadership team in Canada, which is truly inspiring!
Looking ahead to 2025, what emerging trends or technologies do you believe will have the most significant impact on women entrepreneurs in Canada?
According to Square’s latest Future of Commerce report, 2025 is set to be a year of bold innovation and experimentation as Canadian entrepreneurs navigate economic uncertainty. Technology that streamlines operations and enhances customer connections will be crucial. For instance, 89% of restaurant operators say they plan to invest in new technologies this year, and two-thirds anticipate using AI or automation for promotions, inventory management, payments, and menu optimization.
Customer loyalty is also becoming a greater priority, with 70% of restaurant owners planning to boost their investment in loyalty and rewards programs in the coming year. Additionally, 75% of respondents are looking to diversify their offerings—whether through in-store events, subscriptions, memberships, or branded merchandise.
As we conclude, what’s the most valuable piece of advice you would offer to aspiring women entrepreneurs or those looking to advance their careers in the tech industry?
My biggest piece of advice for women launching their careers in today’s fast-evolving world is this: Own your voice, embrace adaptability, and recognize the impact you can have. Be willing to take calculated risks. The business landscape—whether in fintech, hospitality, or any other sector—is changing rapidly, and with that comes both hurdles and opportunities.
Surround yourself with people who encourage you to think bigger and push your limits. Seek out mentors who won’t just offer guidance but will also champion your growth. No matter where you are in your career, having sponsors and advocates is essential. Most importantly, don’t be afraid to claim your space—whether that means asking for the opportunities you want, speaking up in key discussions, or driving meaningful change in your industry. Lastly, stay humble, stay curious, and always be willing to learn—whether it’s mastering a new skill or challenging your own perspective.
