IWD 2026: How Kaydene DeSilva is redefining the ‘boss lady’ narrative
IN the fast-paced corridors of Jamaica’s insurance sector, Kaydene DeSilva stands as a testament to a different kind of power. A young professional, she manages the human resources (HR) portfolio for three general insurance brands within the GraceKennedy Financial Group (GKFG), across multiple countries and personalities; a unique role that requires the precision of a diplomat and the stamina of an athlete.
Yet, if you ask who she is, the answer doesn’t start with a résumé. She starts with a relationship.
“The first thing I want people to understand about me is that I see myself as a highly favoured child of God,” DeSilva shared with a warm, grounded confidence.
“He is at the centre of my life and every decision I make.”
DeSilva’s ascent wasn’t fuelled by a hunger for titles, but by a willingness to step into the unknown.
Her defining moment came during a three-month acting assignment as a senior HR officer for GK General Insurance (GKGI), moving from the GraceKennedy executive office, where she excelled as an individual contributor, to a role with direct reports and strategic oversight was a daunting leap. After her stint at GKGI, she was asked to be the senior HR officer for Key Insurance during a critical merger.
For her leadership, she was aptly rewarded.
“I recall being very nervous about whether or not I was ready,” she admits. “But the opposite happened. I saw myself growing, becoming confident in what I brought to the table and the impact I could make.”
Leadership, as she puts it, isn’t about having all the answers; it’s about modelling excellence and developing potential. It’s a style she describes as “collaborative and leading from the front”.
Earning while learning
In insurance, tenure is often equated with authority, and leading teams that include individuals older or more experienced than herself could have been a hurdle. Instead, DeSilva leaned into transparency.
“I lead with a listening ear,” she explained. “I earn credibility by executing on my tasks, providing sound advice, and being willing to admit when I don’t know the answer. I ensure I do the research and consult the right people.”
This humility has yielded unexpected rewards. She recalls a recent birthday gift from a direct report, items emblazoned with the phrase “Boss Lady.” For DeSilva, it was a moment of profound appreciation. “That title is what I call my own leader out of admiration. Receiving it made me realise I am leaving a positive impact on those I lead.”
Her impact goes beyond the boardroom, with her life being a vibrant mosaic of service and celebration. Whether she is hosting themed events for friends or serving as a director of the Grace and Staff Foundation, her “why” remains consistent. A member of Transformed Life Church, she views leadership as a form of ministry. This perspective has fundamentally shifted her view on career “passion.”
Purpose led to impact
“The popular expression is ‘do what you love’, but my faith has taught me that doing what you are purposed to do is more important,” she noted. “You might be in a certain role for a specific period because your presence there has the greatest impact on others. That is purpose.”
Her advice to young Jamaican women this International Women’s Day is anchored in intentionality.
“Be clear on what ‘balance’ looks like for you. What works for Kaydene might not work for Jane,” she said. “Be intentional about your time. While everything cannot get your attention all the time, ensure each area gets your full attention when you have made the commitment.”
For DeSilva, female empowerment means paying it forward. Doing her part to create the same environments of support that allowed her to flourish. She believes that one doesn’t just lead to reach the top; one leads to lift others as one climbs.
