Kimesha Walters: From invisible to unstoppable

KIMESHA Walters migrated from Jamaica at the height of her career, when she was commanding rooms, leading multi-million-dollar local and international brands, and wielding the authority that comes from knowing one’s worth. But as a new immigrant in Canada, that version of her disappeared. She woke up practically invisible, sleeping on a family member’s couch, and living in their living room — no walls, no privacy, no space to exhale.

The fall was absolute. The rise, however, has been unstoppable. In less than a year she has earned her second major award, most recently being named one of Canada’s Top 100 Black Women to Watch for 2025 by the Canada International Black Women Excellence (CIBWE). This new win is proof that resilience forged in displacement can rebuild faster and stronger than anything built on comfort.

This award underscores the Oasis CEO’s rapid rise as a Jamaican-Canadian trailblazer in leadership and strategic communications. The new accolade follows her September 2024 victory at the Women Empowerment Awards, where Walters won the Mantella Corporation Entrepreneur BIPOC Grant Award, historically, from a record-breaking pool of 243 applicants across Canada.

CIBWE’s prestigious honour recognises black Canadian women who exemplify leadership, innovation, and community impact across a diverse range of fields. What makes this moment even more striking for Walters is the contrast between now and 2018 when she migrated.

“It wasn’t a lack of planning that landed me on my family member’s couch. I am a strategist by design and I came to Canada prepared. I had saved money, created my budget, and mapped out every step. I had made plans to secure a place with family, but at the very last minute, everything shifted,” she told All Woman.

Walters said her supposed flatmate changed plans, and just like that, the strategy she had built around her arrival disappeared. “It was a heartbreaking situation to be in. Reflecting on the setbacks, the struggles related to integration, and the doors that were shut in my face, I am proud of my accomplishments,” she added.

Just like she does for her clients, Walters, an entrepreneur, created a new blueprint for her life, re-strategising, seizing new opportunities, and stepping confidently into unfamiliar rooms where no one expected her. “I refused to stay invisible so I did what I would do for my clients. I took on new roles, marketed myself relentlessly, and sharpened my personal brand to match my aspirations.”

And it worked like a charm.

She has helped transform businesses for entrepreneurs across Canada and elevated leading brands like BMO Financial and Western Union. Through her business, Oasis Integrated Communications, she uses that same strategic expertise to amplify visibility and secure high-impact publicity for her Jamaican clients, including Massy Gas Products Jamaica, Intcomex, ResolveIT, and regional innovator, the Caribbean Climate Innovation Center.

A philanthropist in both Jamaica and Canada, Walters gives back to both countries. In Jamaica, through Amazing Prospect, an education-based charity which she founded in 2010, and volunteering at over a dozen organisations, including the Honey Bun Foundation and the University of Technology, Jamaica and in various capacities for her alma mater, Clarendon College. In Canada her achievements include ecosystem partner for Startup Canada — Canada’s leading entrepreneurship organisation; advisor, mentor, and partner for the Canadian Small Business Women; president of the Clarendon College Alumni Association (Toronto Chapter); and a masterclass presenter for the prestigious Scotiabank Women Initiative, Canada.

But the real gift came from her humble beginnings: raised in a one-room board house in deep rural Prospect, Clarendon, she was forged in an environment where problems were abundant and solutions were survival.

“That’s where I learned to think like a strategist, to see opportunity where others see impossibility, to keep moving when every rational person would quit,” she said. “Those sleepless nights on a family member’s living room couch in Canada simply activated what rural poverty had already taught me: how to build from nothing and refuse the luxury of giving up.”

Reflecting on her journey, Walters said, “This award is a reminder of the grit it takes to stay inspired through difficulties, fight the urge to settle for less-than-ideal situations, and to keep expanding when every fibre of our being tells us to shrink. I’m humbled that my work speaks for itself.”

The CIBWE Top 100 Black Women to Watch in Canada are chosen for embodying the essence of leadership re-imagined and innovation in action.

“Kimesha stood out because of her innovative spirit, heart for service, and unwavering commitment to building a brand that creates opportunities not just for herself, but for the people and communities around her,” said the CIBWE communications team.

“After her Mantella Corporation award win last year we had the privilege of working with Kimesha as our client,” said Sylvia Mantella, vice-president of marketing, sponsorship, and philanthropy at Mantella Corporation. “Her insight, creativity, and ability to turn challenges into opportunities are unmatched. Seeing her recognised by CIBWE comes as no surprise. Kimesha inspires everyone around her to aim higher and achieve more.”

With an expanding client base, Walters is looking to transform marketing communications to get more brands, entrepreneurs, and businesses seen, heard, and remembered.

“Our mission is to continue to lead publicity, content development, and marketing for clients who are doing great work and need a spotlight to continue to increase their reach and influence. We’ll keep telling stories that shift conversations, unlock visibility, and translate directly into growth,” she said.

As a Black Woman to Watch (also known as Black Pearl), Walters will also be featured in the official CIBWE event magazine and receive recognition across the organisation’s platforms. A gala event to honour the awardees was held on Saturday at the Pearson Convention Centre in Brampton, Ontario, Canada.

Kimesha Walters, CEO of Oasis Integrated Communications.