The Spotlight
Gillian Riley
Angel Investor
Gillian Riley is a financial leader and champion for Canadian innovation. As the former CEO of Tangerine Bank, she managed $50 billion in assets and led Canada’s digital banking revolution. Driven by the gaps in women-led financing, Gillian founded The Scotiabank Women Initiative®, which has made access to capital, education and mentorship a priority to 40,000+ women entrepreneurs globally.
Now an active angel investor and Chair of Roynat Capital, Gillian focuses on fueling early-stage tech and building the robust ecosystems necessary to drive productivity and economic growth.
About Gillian Riley
Gillian Riley is a financial powerhouse who doesn’t just lead organizations—she builds movements. With over three decades of experience at the helm of one of Canada’s largest financial institutions, Gillian has mastered the art of scaling businesses and advising the private companies that drive the economy.
Gillian’s career at Scotiabank spanned thirty years of high-impact leadership, culminating in her role as CEO of Tangerine Bank. There, she spearheaded the digital evolution of banking for over 2 million customers while managing a staggering $50B in assets. From leading Scotiabank’s Canadian Business Banking division to overseeing Retail Deposits and Payments, Gillian has spent her career in the trenches with thousands of private companies, advising on everything from M&A and financing to complex succession planning.
In 2018, Gillian turned her insight into action by founding The Scotiabank Women Initiative®. Recognizing that women entrepreneurs were being materially disadvantaged, she championed a pioneering ecosystem designed to shatter barriers to capital, education, and mentorship. What began as a bold vision grew into a global force, supporting more than 40,000 women-owned businesses across the world.
Today, Gillian is focusing her energy on the next generation of innovation. As the Chair of RoyNat Capital, she is deeply involved in private equity and venture funds, while simultaneously serving as an active angel investor and advisor to early-stage tech companies. A "recovering perfectionist" and a believer in the power of a robust Canadian ecosystem, Gillian is dedicated to driving the productivity, innovation, and job creation that will shape the future of the economy.
Beyond her work in Canada, Gillian remains a global leader, serving on the board of Nationwide Building Society in the UK, an institution with 25 million customers and £370B in assets.
On the personal front, Gillian has been married for 31 years to husband, Chris, and is the proud mother of three children. When not working, Gillian is an avid skier, golfer and tennis player who loves spending time at the family farm just south of Collingwood, ON.
Connect on LinkedIn: Gillian Riley
Company Snapshot
Investment Focus: Founders who have a passion for the business, know their competition and how they will win. Women founders are important in my focus.
Investment Philosophy: Prioritize building genuine relationships with leadership teams, believing that people are the ultimate predictor of success. Balance this personal approach with a sharp focus on financial acumen and technical know-how.
Unique Edge: Gillian brings a powerhouse network and a panoramic view of the Canadian business landscape. Having spent decades advising diverse industries across the country, she offers founders rare cross-sector insights and the high-level connections needed to scale.
Committed to: Being a relentless champion for the Canadian venture landscape, deeply committed to architecting a more robust and inclusive ecosystem for women founders.
The Spotlight: A Conversation with Gillian Riley
Interviewed by Sherry Shannon-Vanstone, Co-founder & CEO, Women Funding Women Inc. (WFW).
Published February 8th, 2026
Sherry: We’re excited to welcome Gillian Riley as our featured funder for The Spotlight, presented by Women Funding Women in partnership with The Scotiabank Women Initiative®. Thank you for speaking with me today. Gillian, let’s start with you. Tell us a bit about your journey to becoming an investor.
Gillian: Thank you for this opportunity to be featured on The Spotlight. I spent more than 30 years at Scotiabank in a wide range of roles, but much of my career focused on working with private companies of all sizes - advising on financing, M&A, succession planning, and investments. Over time, you start to see patterns. It’s not just about what companies do; it’s really about the people behind them and how they build it.
That perspective shaped my journey into investing. Now that I’ve retired from the Bank, I’m excited to put my energy and my capital into things I believe are important. I’m a strong believer that Canada is ripe for investment. Investing here drives innovation, jobs, productivity, and ultimately strengthens the economy. That’s the core thesis behind what I do.
And when it comes to women, that focus is critical. Women have historically had a harder time achieving success in business. Progress has been made, but there’s still a long way to go. For me, it’s about building women’s capabilities and confidence across the investment ecosystem in multiple ways and that’s a major focus of my work.
Scotiabank Women Initiative
Sherry: While you were at Scotiabank you founded The Scotiabank Women Initiative, which is now a partner with Women Funding Women (WFW) for The Spotlight. What motivated you to launch it?
Gillian: At the time, I was leading Scotiabank’s Canadian business banking division. I was on a panel with several women entrepreneurs, and they began talking about how difficult it was for women to access capital. In fact, one founder mentioned how she had been turned down more than 20 times for financing early on. That really stopped me in my tracks.
Here I was a woman leading a business banking division at a major financial institution and I was hearing firsthand how big this gap was. I started digging into the data with a team at the Bank, and what we found was shocking. Less than 4% of venture capital dollars were going to women-led companies. Only about 15% of businesses were founded or run by women. For SMEs, I would have expected that number to be much higher.
I felt a responsibility to act. As we researched further, we realized it wasn’t just about capital - it was about mentorship, networks, and education. It was the entire ecosystem. That insight led to the creation of The Scotiabank Women Initiative.
What made it successful was that an entire community inside the bank rallied behind it. We created mentorship boot camps, brought in experts across marketing, HR, finance, and technology, and built spaces where women founders could learn from and support each other. During COVID, we even built an online portal to help founders move their businesses online. What started in Canadian commercial banking grew into a global movement across countries, divisions, capital markets, wealth management, and board representation. It’s incredible what can happen when people come together around something that truly matters.
Sherry: It must be deeply meaningful to see what you started become part of your legacy.
Gillian: It is, but what I’m most proud of is how people took ownership of it. They made it their own and continued to move it forward. That’s how movements sustain themselves.
As the President & CEO of Tangerine Bank
Sherry: You were also President and CEO of Tangerine Bank. Can you tell us about that experience?
Gillian: I spent six years as President and CEO of Tangerine Bank, Canada’s leading digital bank. When people hear “digital,” I remind them that Tangerine has no branches - everything is powered by technology, with mobile banking at the forefront. What I loved most about that role was deepening my understanding of technology, particularly emerging technologies like AI and machine learning.
But just as important was Tangerine’s unwavering focus on the customer. Tangerine has consistently ranked number one in customer
satisfaction among Canadian banks, and that’s something I’m incredibly proud of. I’ve always had a deep respect for customers - serving them well and giving them what they truly need. Being able to build simplified processes and meaningful solutions that saved people time and money was a highlight for me.
And I’ll add that Tangerine is a vibrant bank with lots of energy. Marketing was extra important, and being the Bank for the Toronto Raptors and celebrating their championship win was pretty special
The Next Two Years
Sherry: That must have been an amazing time to be at Tangerine during the Raptors championship. Let’s talk about what you’re doing now, including your role as Chair of the Board of Roynat Capital.
Gillian: I oversaw Roynat while at Scotiabank while leading the business banking division and it’s a differentiated offering too. Roynat is unique in Canada – it provides financing solutions for small/med sized businesses and it also invests in venture /private equity funds. I have been very happy to continue to support them as the Chair of the Board.
I’m also investing with The Fund51 in Calgary, and I’m an Executive in Residence at the DMZ at Toronto Metropolitan University, where I work closely with early-stage ventures.
What frustrates me is how hard it is to raise capital for women-focused funds in Canada. We really need to build stronger ecosystems for emerging fund managers - especially women.
Mobilizing Women Angel Investors
Sherry: Several women fund managers across Canada are members of the WFW’s Women Advisory Council and they are doing important work. You’re also a member of the Advisory Council. How do we mobilize more women to become angels and venture investors?
Gillian: Awareness is the first step. When people truly understand the gaps, they’re often motivated to act. But we also need to create environments where success and learning from failure is supported.
We’re not always great at learning from failure, especially women. Men tend to have stronger support systems when things don’t work out. Women are often harder on themselves and on each other. That’s why men need to be part of this equation. This isn’t just about equity; it’s about economic growth, innovation, and productivity.
Taking Risks
Sherry: You mentioned failure, and I think that’s something women often fear. I’m a recovering perfectionist myself. How do we help women become more comfortable taking risks?
Gillian: I love that phrase - recovering perfectionist. Perfectionism can make failure feel unacceptable, when in reality, it’s a powerful teacher.
As an Investor
Sherry: You’re also an active angel investor. What’s your core investment thesis?
Gillian: It always comes back to the people. Do the founders understand their market? Are they passionate? Do they know what they’re trying to achieve? Do they understand the numbers? I tend to gravitate toward technology, but ultimately, it’s about the founders.
Advice to Women Founders
Sherry: Once you’re interested, how do you approach due diligence?
Gillian: I’m very focused on the numbers – short- and medium-term goals, assumptions, TAM, differentiation, and focus. Drift is often what causes companies to fail. Staying close to the core thesis is essential in the early years.
Sherry: What are your non-negotiables before investing?
Gillian: Valuation, cap table clarity, thoughtful planning for future rounds, and integrity. I always check references. And founders and their management team must have skin in the game - that’s non-negotiable.
Sherry: What advice do you give women founders?
Gillian: Be confident and be clear. If you don’t know something, say so and explain how you’ll get the answer. Don’t hedge or fudge. Practice your story. Investors form impressions quickly, and preparation matters.
I recently watched three women pitch - two were exceptional, one wasn’t prepared. Guess which two I wanted to invest in.
Sherry: Final thoughts for our readers?
Gillian: Build a safe network not just a network of investors, but people you can turn to for honest feedback and support. Founders need that, especially when things get hard. I often suggest creating a small peer group - founders helping founders.
And investors should support each other, too. That sense of community is powerful.
Wrap Up
Sherry: Gillian, thank you so much for this conversation and for your continued leadership with Women Funding Women. I know that our readers of The Spotlight will enjoy hearing about your journey.
Gillian: Thank you. I’m really looking forward to continuing the work together.
Key Learnings & Advice from Gillian Riley
For the movement
"True progress for women in business happens when we stop focusing solely on the transaction and start building the ecosystem. By combining capital with mentorship, education, and a safe network to fail and learn, we create a movement that sustains itself."
Establishing your community
"Build a safe network—not just a network of investors, but people you can turn to for honest feedback and support. Founders need that, especially when things get hard."
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