Keisha Bailey, global financial strategist and founder of Bailey Wealth Group & Profit Jumpstarter, has been named among Canada’s Top 100 Black Women to Watch by Canada International Black Women Excellence (CIBWE). 

The award recognises and celebrates women who lead with purpose, drive innovation and have achieved groundbreaking milestones in their careers and have made a lasting impact in their communities and beyond. 

Bailey has been recognised among a powerful network of changemakers in Canada, shaping the future of business and leadership, through her work in empowering Caribbean nationals and the diaspora to create wealth and build a legacy for future generations. 

Previously featured among outstanding leaders in business – 2024, she was highlighted as one of the transformative leaders driving progress across the Caribbean. From Jamaica to the wider region and now Canada, her journey continues to inspire the next generation of visionary leaders as she redefines business without borders.

“I am honoured to be acknowledged with this award, among other outstanding women, for my dedication to empowering individuals to transform their lives and build lasting legacies through wealth creation. This award further fuels my passion to create opportunities to improve financial literacy and support individuals to achieve financial freedom,” shared Bailey. Adding, “It is a testament to the achievements thus far in this area and serves as an impetus to drive progress in transforming this generation and the next. In keeping with this mission of building wealth, I will be hosting a series of events, including a workshop for entrepreneurs in November on taxation and investment strategies.” 

In congratulating Bailey on the occasion, CIBWE stated, this prestigious recognition, celebrated at the annual Black Pearls Gala (to be held on October 25 at the Pearson Convention Centre, Canada), honours the outstanding achievements and rise of Black women across various fields, including entrepreneurship & business, professional/corporate sectors, athletics, arts and media, and youth. Your selection is a testament to the remarkable impact you are making through your work and accomplishments.

Now in its 10^th year, the awards are not just accolades—they are a tribute to legacies being built and a recognition of the enduring contributions Black women continue to make in shaping Canada’s social, cultural, and economic landscape. The visionary behind the CIBWE awards, Cameroonian immigrant-turned-Canadian business leader, Rose Cathy Handy, founded this platform to celebrate and inspire the remarkable achievements and contributions of Black women through events, publications, training, social enterprise and capacity building. Awards like these showcase the diverse talents and accomplishments of black women, while challenging stereotypes and inspiring future generations.