Women, Tech & The Future of Business: Insights From Square Canada’s Liz Samson

As International Women’s Day approaches, we’re shining a spotlight on women driving change in the business and tech world. Liz Samson, Square Canada’s new Head of Industry Relations and Operations, brings years of fintech leadership from WealthSimple and RBC. She’s not only a trailblazer in the industry but also a champion for women-led businesses, offering key insights into the evolving economy, the power of female entrepreneurship, and what it takes to succeed in tech. —Noa Nichol

As one of the most senior women at Square Canada, what does leadership mean to you, and how has your journey shaped the way you lead?

Over the past few years, Canadian business owners have had to navigate unprecedented challenges. Every day, our team at Square asks: How can we make it easier for businesses to grow and thrive in Canada? And every day, we take action—whether it’s by building innovative tools to help businesses grow and thrive, advocating for businesses of all sizes or building strong relationships with industry partners, which is a big focus of what I do.

To me and my team, equipping Canadian women—both aspiring and established business owners—with the tools, resources, and support they need to dream big and turn those dreams into reality is our driving purpose. It’s about actively removing systemic barriers that have historically made it harder for women entrepreneurs to grow their businesses on their own terms.

Square Canada data shows that over half of business owners on the platform are women. What does this say about the current landscape of women-led businesses in Canada?

Women entrepreneurs are a powerful force in Canada and a catalyst of local economic growth. Our data shows that 3 in 4 women-led business owners on our platform say Square gives them control of their destiny as entrepreneurs. That’s fantastic, and it’s the kind of impact that fuels my work—helping women take control, scale their businesses, and strengthen Canada’s Main Street economy so they can stand as strong as Bay Street.

What are some of the most exciting and fast-growing women-led restaurant concepts and businesses that have caught your attention?

I’m continually inspired by the innovative and fast-growing Canadian women-led businesses that are reshaping our industries. A remarkable example is Knix, which has revolutionized the intimate apparel industry across the globe. Smash + Tess is another popular women-owned Canadian fashion brand that quickly gained a loyal following thanks to its focus on size inclusivity and sustainable fabrics.

From a food industry perspective – which has been historically male dominated – I’m very impressed by women like Nicki Laborie. Her passion for creating a memorable restaurant experience has grown from her initial restaurant, Reyna, in 2016, into Reyna Hospitality Group, which now has various locations in both Toronto and New York. I’m thrilled to see these shining examples of women-owned companies and brands that are continuing to grow and thrive despite the many challenges businesses of all sizes have faced in recent years.

The economy has been challenging for many small business owners. What are the biggest hurdles women entrepreneurs face today, and how is Square helping to support them?

One of the biggest challenges I’ve seen small businesses face in recent years is trying to navigate rapid change—whether it’s shifting consumer expectations, evolving regulatory landscapes, or the increasing need for seamless digital experiences. Small and independent businesses, in particular, often face an uphill battle to adapt to these changes while maintaining their unique identity and community presence. 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.

You’ve had an impressive career spanning fintech and banking, including time at Wealthsimple and RBC. What drew you to the tech space, and what has kept you inspired?

I started my career over 20 years ago in tech at Hewlett Packard, in supply chain. From there I transitioned into financial services, holding leadership roles at RBC and Wealthsimple, where I worked on payments, banking partnerships, and scaling brokerage operations. A common theme has been transformation and innovation. After spending over a decade at RBC, I was drawn to fintech as I’m energized by the speed of change as well as the empowerment of the end user that tech delivers. Financial services are critical and ubiquitous, so there’s an opportunity to have an outsized impact on people’s wellbeing and success. Tech companies approach problems differently – I think a lot of them have a relatively unconstrained view of the future and what’s possible, and people in the industry have a creator’s mindset, which appeals to me.

Canada and the world needs more of this, and there is so much whitespace. I’m grateful to play a small part in shaping the future and being at the heart of it. This is what fuels my passion for tech and fintech, in particular.

What’s the best leadership advice you’ve ever received, and how do you apply it in your daily work?

There’s no one piece of advice that I can put my finger on, but what I can definitively say is that having a strong network of mentors and managers has helped me immeasurably in modelling my leadership style throughout my career. I’ve been fortunate enough to work for some incredibly talented leaders and I’m always reflecting on what behaviours I can emulate and adopt to become a better leader. It takes active practice and experimentation to incorporate new behaviours and approaches into your leadership style. It’s a work in progress. There’s also value reflecting on leadership behaviours that are ineffective, and these ones really stick out. As much as I focus on making positive changes, I’m also very aware of avoiding poor leadership practices as these can really undermine your effectiveness as a leader.

What keeps you up at night? And on the flip side, what excites you most about the future of women in tech and entrepreneurship?

Our data shows that approximately 4 in 5 women sellers on the Square platform accepted card payments for the very first time thanks to Square’s tools. That’s an incredible milestone, and it speaks to the impact of providing simple and integrated solutions that help sellers operate their businesses more efficiently. Whether it’s a small café operator, a multi-location restaurant owner, a beauty professional or a professional services business, we’re committed to empowering entrepreneurs with the technology and support they need to take their business to the next level.

Many women entrepreneurs struggle with self-doubt and imposter syndrome. How do you stay focused and tune out the noise in your career?

My biggest advice to young women starting their careers in today’s fast-moving and often unpredictable world is this: Own your voice, stay adaptable, and never underestimate your ability to drive change. Don’t be afraid to take risks. The business landscape—whether in fintech, restaurants, or any other industry—is evolving rapidly, and with that comes both challenges and opportunities.

If you could craft a ‘success menu’—a set of must-have ingredients for leadership and growth—what would be on it?

Surround yourself with people who lift you up and challenge you to think bigger. Seek out mentors who will not only guide you but advocate for you. No matter what career stage you’re in, sponsorship is crucial. And most importantly, don’t be afraid to take up space—whether that means asking for the role you want, speaking up in a room full of leaders, or pushing for innovation in places where it’s needed most. Finally, be humble and curious, and continuously challenge yourself to learn. This can be a new skill or changing a previously held perspective.