Meet Jackie Chambers de Freitas: Caribbean Woman in Tech Leadership

 There’s a cultivated fortitude that comes from being the only one in the room and deciding that this is exactly where you belong. Jackie Chambers de Freitas has spent more than 30 years in that room. As vice president of AI delivery and transformation, she sits at the intersection of technology, innovation and organizational change, an industry that rarely made space for women who looked like her when she started. It still doesn’t always, but Jackie has never been in the business of waiting for permission.

Born in the United Kingdom to Jamaican parents and raised across cultures after moving to the U.S. in her late teens, Jackie describes herself first as a global citizen. That layered identity, shaped by multiple countries and communities, became the foundation for how she leads today. “My Caribbean heritage is foundational to who I am,” she said. “It instilled resilience, pride and a deep sense of community. I was raised to believe in working hard, standing tall in who I am and not shrinking myself to fit into spaces.”

Showing Up Whole

For Jackie, representation isn’t an abstract talking point. It’s a daily practice. As a Caribbean woman in senior tech leadership, she carries an awareness that her presence in certain rooms is both rare and necessary.

“It’s about more than just holding a title,” she said. “It’s about visibility, impact and challenging what leadership is supposed to look like.” She doesn’t separate her cultural identity from her professional one. The way she speaks, connects and leads is shaped by where she comes from, and she treats that as a strength rather than something to soften.

[Additional Read: She Built Businesses from $40: Shelly-Ann Aqui Solomon on Caribbean Identity, Legacy and Unapologetic Success ]

If someone else can see me and think, ‘There is space for me here too,” then that is powerful.

Naming What’s Real

Jackie doesn’t shy away from the harder parts of the conversation. Racism and sexism, she admits candidly, are still part of her working life, sometimes subtle, sometimes not. But acknowledging that reality isn’t defeat. It’s clarity.

The hurdles don’t magically disappear just because you earn a senior title, she said. The bias simply becomes more sophisticated.

Her advice for women navigating male-dominated industries is refreshingly tactical. Stop waiting for an invitation and start owning your intention. Build a strategic circle of sponsors who advocate for you in rooms you’re not in. When microaggressions surface, meet them with calm, direct questions that force people to sit with their own words. “Own your decades of expertise,” she said. “Bring your full, authentic self into the room, and build a personal brand that commands respect exactly as you are.”

From Obstacle to Advantage

Jackie’s origin story in tech began more than 30 years ago, when there were, as she puts it, “very few blueprints for someone like me.” She was often the only woman in the room, frequently the only woman of color. Rather than wait for a clearly defined path, she raised her hand for the ambiguous, high-stakes projects others avoided.

The real turning point in her leadership journey came when she stopped seeing her gender and race as disadvantages and reframed them entirely. “They represent a unique lived experience and a distinct point of view that I bring to the table,” she said. That shift changed everything. She stopped trying to fit a corporate mold that was never built with her in mind and started treating her perspective as a competitive edge.

I stopped trying to prove I belonged, she said, and started knowing that the room was smarter and more capable simply because I was in it.

Leading With Both Strength and Humanity

Ask Jackie to define her leadership philosophy and she’ll tell you it has evolved considerably. Early on, she equated leadership with authority and having every answer. Experience taught her otherwise.

The best leaders listen, uplift others and create environments where people can thrive, she said. It’s about leading with both strength and humanity.

That philosophy extends visibly into how she presents herself. Style, for Jackie, is not incidental to leadership; it’s part of it. As a Gen Xer who embraces fashion and self-expression fully, she sees dressing boldly as its own quiet form of authority.

It’s not about following rules, she said. It’s about owning your presence and feeling good in how you present yourself. You don’t have to conform to be taken seriously. You can be both polished and expressive.

Building the Floor for the Next Generation

When asked about legacy, Jackie’s answer is immediate and clear: People cannot become what they don’t see. She wants her career to serve as visible proof that women of color can rise to the highest levels of global leadership without compromising identity, style or values.

I want my ceiling to become the starting floor for the brilliant leaders following in my footsteps, she said.

Her advice for young Caribbean women eyeing corporate or tech spaces is simple but grounded. Believe you belong, even before you see people who look like you in the room. Invest in your skills. Stay curious. Take the risks. Find mentors, build community and never forget that your voice and your culture are assets, not liabilities.

Follow Jackie’s journey on LinkedIn and Instagram.