Alanna Medford-Singh has spent nearly 20 years shaping cricket in the West Indies from a legal and administrative vantage point. As the first in-house counsel for Cricket West Indies, she oversees governance, contracts, and commercial rights across the organization, ensuring that both domestic and international operations run smoothly. “Straight out of school and landing this opportunity—it was dream job,” she recalls of her early work on the 2007 World Cup, a role that would define her career.

Her experience spans the transformation of Caribbean cricket through the rise of the CPL, the growth of domestic leagues, and evolving player regulations. “We were all trying to figure out how to navigate this world that cricket is becoming, and it’s still continuously evolving,” Medford-Singh says, emphasizing the strategic and legal challenges she has navigated for nearly two decades. Her guidance touches every facet of the sport, from player contracts to regulatory frameworks, and she has been central to advancing West Indies cricket on the international stage.

Beyond her organizational responsibilities, Medford-Singh has helped harness political support to strengthen the sport. “Almost every prime minister of the West Indies is the biggest cricket fan in that country. They also have an interest in making sure that cricket is run smoothly,” she explains, highlighting how high-level alignment has enhanced events like the 2024 World Cup.

As one of the few women at executive leadership level, she continues to set a precedent and acknowledges the support she has received. “I’ve had presidents, I’ve had CEOs who’ve all supported me on that journey. There have also been inspiring women around the West Indies who support what a young female professional can do in this very male-dominated world.” Her presence ensures that women’s perspectives are heard in strategic discussions about player development, governance, and the commercial growth of cricket.

For aspiring female administrators, she emphasizes confidence and self-trust. “You have to be confident, you have to trust your own voice, you have to not listen to what everybody else around you might be saying.” Medford-Singh’s continues to demonstrate the impact of expertise, perseverance, and leadership as a pivotal figure in the governance and evolution of West Indies cricket.