“Take care of the pennies and the dollars will take care of themselves.”
It’s a lesson Sheila Yendt learned from her father, one that shaped not only her approach to money but also her approach to life.
In many ways, her career has followed the same philosophy. As a young mother, stepping into the wealth management industry in a part-time position, she didn’t enter with a master plan; she entered one day a week.
It all started with Christmas tree shopping. Sheila ran into a friend who worked at RaeLipskie Partnership, who mentioned they needed some help in the office, which was just down the street from her home.
She started working one day a week in an administrative role at RaeLipskie Partnership, answering phones, entering data, and filing paperwork. Eventually, Sheila worked up to three days a week, “Which was great,” she recalled, “As a young parent, I was able to be home a lot with my kids, and they were a flexible employer.”
These early days were foundational, “I was very curious, and they let me try many different things,” she shared. Although she was never particularly fond of traditional school, she loved and still loves learning. “I found other ways to learn, and resources to help me.” After passing the Canadian Securities Course, she moved into trade processing, client services, and eventually stepped into people management and grew alongside the company.
RaeLipskie Partnership had a small team then, and everyone did a bit of everything. This environment nurtured Sheila’s love of learning and curiosity, and gave her a deep, lived-in experience and knowledge of how the business works.
Today, as Deputy Chief Operating Officer, Sheila plays a central role in guiding RaeLipskie Partnership’s operations. From financial oversight and facilities management to HR coordination and working alongside their parent company, Guardian Capital Group, her focus is on ensuring that systems, staff, and infrastructure are aligned so that portfolio managers can focus fully and confidently on their clients.
Alongside her operational leadership, Sheila is passionate about increasing female representation in the industry and actively supporting their growth and advancement.
Despite decades of progress, wealth management remains a male-dominated field. While women are projected to control nearly $4 trillion in financial assets by 2028, men still hold an overwhelming portion of financial advisor roles in Canada, at 80-85%.
“There is a true lack of women in this space, and firms are desperately looking for female advisors. Women are very good at this type of work.” Sheila shared. “At our firm, we have fiduciary advisors, which means we have a duty by law to put our clients’ best interests first. It is a highly regulated profession, requiring us to take care of our clients and behave in a manner that upholds the integrity of the industry – that responsibility truly resonates with me. There’s also a great deal of variety in this field, from client care and research to compliance and advising. And importantly, it offers the opportunity to build a meaningful and rewarding career.”
For her, female strength is rooted in connection. Shifting the relationship from transactional to client-centric means walking alongside someone through life’s changes, market shifts and retirement plans; it’s about trust, and women bring a powerful capability to cultivate it.
In her role today, Sheila promotes this connection within RaeLipskie’s culture, supporting team members, encouraging collaboration and making sure everyone knows sometimes mistakes are part of the learning process. “I teach every person when they start in this role, mistakes happen, and whatever you do, just stop. Take a breath. Let’s calmly work together to fix it.”
Guided by a motto she carries with her into every meeting, task, and role, “Do the right thing, thoughtfully,” she leads with intention. Grace and patience are embroidered in her leadership approach, and in this environment, people, especially women, grow.
Still, representation matters.
Nearly 75% of women in executive and professional leadership positions experience imposter syndrome at some point in their careers. Sheila knows that feeling and works against it.
“To walk into a conference full of mainly men and see a woman stand and speak as the expert she is, it’s still a little shocking. Why am I so impressed? We shouldn’t be that impressed anymore. It should be normal,” Sheila recognizes.
Having started in an entry-level position, she lived through every transition. Each step forward brought new expectations, and at times, new doubt. But her advice really hits home, “Don’t be afraid. What you have to say and contribute matters.” And with that, she continued, guided by her curiosity and willingness to rise to the challenges along the way.
Support has also played a critical role in her journey. “Ken Rae and Brian Lipskie, the founders of RaeLipskie, were a huge influence for me; they supported and encouraged my opportunities, they gave me important advice and sometimes critical feedback. During COVID, when my resilience started to wane, Brian shared with me, ‘Control what you can control, have faith that good things will happen, and keep moving forward.’ This really gave me perspective, and I lean into it often.”
Sheila is also supported and inspired by her five sisters and one brother, who each have become incredibly successful in their fields. “My parents encouraged us that we could do anything; there was never a feeling that we weren’t capable or that opportunities wouldn’t be open to us.” Instilling in their children a lasting message of confidence, ‘Be curious, be professional, you can do it, kid.’”
Mentorship, encouragement and education have shaped her path, and she believes these forces are especially important for women entering wealth management – as advisors and as clients.
From instilling financial literacy in her daughters to advocating for financial independence in women, Sheila emphasizes ownership. She explains that understanding your wealth, knowing where your money is going, setting your own wealth goals, and building a wealth plan is a way to achieve that ownership and autonomy. “Don’t wait for someone else to take charge of your financial future, take the initiative, seek guidance when you need it and keep asking questions until you feel confident and informed, especially when it comes to your own wealth.”
And as fewer women today face the choice between career and family, Sheila’s own path reflects that possibility. “Work gave me fulfillment in a different way than parenting, and the workplace allowed for that balance.”
From foraging a career that began humbly back in the 1990s, Sheila now leads with steady confidence guided by her deep industry and company knowledge. Her experience is woven into the foundation of RaeLipskie, built on years of showing up, exploring, attempting and learning new things, falling and getting back up again.
Inspired by the women who work alongside her and by the journey that shaped her, this International Women’s Day, and every day, Sheila hopes for a future filled with more women’s voices, expertise and leadership in the investment industry and all walks of life.
Reminding women everywhere not to be daunted, “You bring a perspective to the table that is important and influential. Life is long, enjoy the journey, be curious, be kind, you can do it!”
From data entry to Deputy Chief Operating Officer, none of this happened overnight; it was built day-by-day, year-over-year, small moments of courage, lessons learned, curiosity, and confidence accumulated. What once felt incremental has compounded and is yielding lasting returns.
And over time, those pennies turned into dollars, into leadership, into influence, into a seat at the table she earned.
Happy International Women’s Day.
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