Meet Stachen Lett-Frederick, the CEO Championing Youth Mentorship and RBC Canadian Women Entrepreneur Awards Social Change: Regional Impact Winner

By Khera Alexander

“From the early age of eight, I told my mother that I was going to go abroad to work with children and youth.”

That clarity shaped Stachen Lett-Frederick’s entire career.

Growing up in Trinidad & Tobago, her passion for child and youth work only deepened as she got older. But after immigrating to Canada, she saw firsthand how many young people were underserved and vulnerable — and she wanted to be part of the solution.

When she moved from Ottawa to Toronto, she took an entry-level job at the YMCA, quickly rising through the ranks. Her willingness to step up, take on new responsibilities, and demonstrate leadership set her apart. But it was a conversation with the YMCA’s CEO that gave her an entirely new perspective on what she wanted next.

A Career-Defining Conversation

As Director of Youth Community and Employment Programs, Stachen reached out to then-CEO Medhat Mahdy for a meeting.

“I want your job,” she told him.

Instead of brushing her off, he asked her why — three times.

The conversation forced her to strip away the prestige of the title and dig into what truly motivated her. Did she really want to lead the YMCA?

The answer was no.

“I actually figured out through those three whys that I didn’t want his job — not just because of how long it was going to take, but because it wasn’t what I wanted for my career.”

She realized that while the YMCA served people of all ages, she was most passionate about youth-centered work. That clarity changed everything.

So when the Executive Director position at Weston Frontlines Centre opened up, she knew it was where she needed to be.

Turning a Struggling Charity Into a Nationally Recognized Organization

Weston Frontlines Centre was at a breaking point. The small charity, located in one of Ontario’s poorest ridings, was struggling to stay afloat.

Others may have seen it as a risk. Stachen saw it as an opportunity.

She doubled down on transparency, built trust with funders, and streamlined operations — ensuring that every investment created real impact.

“I am extremely passionate about the work, about the organization, [and] about the Black youth I serve,” she says. “I was [also] very much into running the business from a lean perspective. When funders are able to see that a business is making different touchpoints and connections for them and a greater impact on the value of their money, they’re more inclined to support.”

Under her leadership, Weston Frontlines grew into a $5 million organization, now ranked as one of Canada’s Top Youth Engagement Charities.

But the entire time, she was thinking ahead.

Manifesting Her Next Chapter

Even in 2016, Stachen knew what was next.

“I knew that Frontlines was going to succeed underneath my leadership,” she says. “Such that within eight to ten years, when the position for Big Brothers Big Sisters of Toronto comes up, I would be in the position to apply for it.”

In 2024 — eight years later — she stepped into the role of President & CEO.

A Win That Marked the Transition

Just as she was preparing for her next chapter, one final milestone cemented her impact at Weston Frontlines: winning the RBC Canadian Women Entrepreneur Award for Social Change: Regional Impact.

Her nomination came as she was wrapping up her tenure at the organization, but she knew she had built something worth recognizing.

“When I filled out this application, some of the fruits of my labour, such as writing a $7 million grant, came about during this nomination. It was the right time, and everything perfectly lined up.”

Winning was about more than personal achievement — it was about ensuring Weston Frontlines’ legacy.

“Frontlines was my baby,” she says. “I knew I was transitioning out, and knowing how prestigious this award is, I wanted to ensure the legacy and recognition happened while I was still at the helm.”

Now, she’s focused on scaling her impact even further.

The Future of Mentorship in Toronto

In her new role at Big Brothers Big Sisters of Toronto, Stachen is focused on one thing: connection.

“We have a mental health crisis on our hands, and so much could be mitigated when people have connection, and they don’t feel lonely,” she says.

Her vision is to build a mentorship hub — a space where youth can find guidance, support, and opportunity outside of traditional models.

“I want to create a center of mentorship where youth are able to connect with mentors — people in the community who don’t have the designation of Social Work attached to them. A place that’s a center for research and filled with points of connection for young people. That is what I am excited to see materialize and what I dream of coming to life.”

With a track record of turning vision into reality, she’s well on her way.