The Rise of Women Leaders in the Caribbean

The state of leadership in the Caribbean is changing – from a top-down, authoritative approach, to more open, learning-based environments. Part of this is due to the rise of women leaders in the Caribbean and part due to a generational handover to a new wave of leaders.

According to the International Labour Organization (ILO) Jamaica has the highest percentage of female managers in the world at 59.3 per cent, with six Caribbean nations ranking in the top 15 globally. However, at the most senior levels of leadership – in the C-Suites and boardrooms in the Caribbean, men still dominate.

Ageism has also been a challenge, with younger leaders not being seen as credible, despite bringing new skills and styles to the table. Thankfully these traditional, slower-paced company cultures have been changing over the past few years – I myself have been a beneficiary of this change. At 33, I am a young, female leader of an organisation with an incredible brand. The backing of this brand, along with a great education, has helped me to overcome many challenges.

When I reflect on the role of leaders across the Caribbean, and on what is catalysing the recent changes, the following drivers come to mind:

  1. Having a critical mass of female managers who are poised for promotion to the highest levels of leadership in the region
  2. The influence of the Silicon Valley style of leadership – with very young tech CEOs who have redesigned offices and office cultures
  3. A handover from an earlier generation of business owners to the next generation, who have often studied and gained experience abroad before coming back with new approaches
  4. The re-emergence of entrepreneurship as desirable path, resulting in dynamic new businesses with dynamic leaders
  5. Companies like the Virgin Group entering the Caribbean markets and changing mind-sets about leadership and company culture

It’s important for all young business people to remember that before you become an official ‘business leader’, your focus may be very narrow – often on one area of the whole operation. Once you become a leader, you need to understand everything at once – you have to trust your team to handle the details, while developing an operating system to check in consistently and ensure you’re still aware of what’s happening.

The key ingredient here is having a team comprised of masters of execution, people who you trust to do some serious heavy lifting and who will free you as the leader to go broad. My own system is to have four direct reports, who each handle a major area of the business. Our company is still small enough to ensure this works well. Each day of the week is allocated to checking in with one of the four, and clearing my inbox of all activities related to that area. I try to leave Fridays for strategic items. Of course this structure is flexible, but having it as a default guide has been really helpful.

To me, Sheryl Sandberg embodies the impact that a strong leader with a soft touch can have on a company. Facebook has grown from strength to strength since she joined the team. She is COO of Facebook, has written two incredible books, started a non-profit organisation, started a family, dealt with the shocking loss of her husband, all while exuding both strength and vulnerability.

Learnings from Sheryl, from Richard Branson, and from the countless mentors, entrepreneurs and friends that I have spoken to throughout my journey , have helped me distil my top list of leadership qualities to the three  below. Enjoy and please share your thoughts with me about the future of leadership and entrepreneurship in the Caribbean.

  1. Authenticity – if you try to adopt someone else’s leadership style, you won’t connect or inspire. People can tell when you’re being inauthentic from a mile away.
  2. A Strategic mind – in order to steer the ship through headwinds and uncertainty towards achieving the mission
  3. The ability to spot, recruit and develop other leaders, and to develop a system that does this throughout the entire organisation.

*Originally published on