Style Observer (SO):
You are a noted executive in the insurance industry. Was this a calling or something that you worked towards and continue to work at?

Sheraley Bridgeman (SB): It has been a journey. While I did not initially set out to join the insurance industry, once I entered the field, I found a deep sense of purpose in the work. The combination of finding the right insurance solutions at the most affordable price to help people protect their assets and their future resonated with me pretty early in my career. Over time, I have committed to learning and also giving back to my industry, as I now lecture at the College of Insurance and Professional Studies. I am also adapting to the changing needs of the clients and of my various roles and continue to grow and refine my leadership and expertise everyday.

SO: How has the industry evolved over the decades?

SB: The insurance industry has undergone a significant transformation since I entered over 30 years ago, particularly with the advent of technology. We have moved from traditional paper-heavy operations to a more agile and tech-driven approach. Clients now expect personalised, efficient service and we have adapted by offering digital platforms, inclusive products, tailored risk solutions and greater emphasis on financial literacy and wellness.

SO:
How do you stay motivated and by extension keep team members motivated?

SB:
I stay motivated by remembering the “why” behind our work — protecting people’s assets, lives and their futures. To keep my team motivated, I prioritise open communication, team building, rewards and recognition and opportunities for growth. Empowering others and celebrating wins, no matter how small.

SO: What are you most passionate about?

SB:
I am deeply passionate about making a difference in my industry through empowering individuals to recognise their full potential. Creating environments where people feel seen, supported and inspired to grow is at the core of my leadership approach. Equally, I am committed to increasing public awareness about insurance in Jamaica. Too often, individuals underestimate how vital insurance can be during times of crisis, largely due to lack of understanding. My mission is to help bridge that knowledge gap so that more persons can be prepared to navigate life’s uncertainties with proper insurance.

SO: Share with us a few career highlights.

SB: There have been many highlights. In previous roles, I have successfully developed and launched a range of insurance products. Queen Guard is my favourite so far! I have also played a key role in driving transformation within one company, spearheading the implementation of eCommerce platforms and transitioning the operations to a paperless environment. Most recently, I have had the privilege of leading the Caribbean Assurance Brokers team through a significant transformation and we are now beginning to see the tangible results of that journey. Whilst these accomplishments are meaningful, what resonates most is witnessing the growth and success of individuals I have mentored, coached or trained. Seeing them thrive in their own careers brings me immense fulfilment.

SO: With Emancipation and Independence mere weeks away, what steps would you take to truly galvanise the people of Jamaica around the significance of this holiday?

SB: We need to move beyond viewing these commemorations as just ceremonial or another holiday. By promoting education, community engagement and intergenerational dialogue we can help Jamaica, especially our youth, connect with the richness of our history and the responsibilities of true freedom. It’s about fostering unity, that Jamican pride and forward momentum.

SO: Which three women (locally or internationally) inspire you? And why?

SB: Mia Mottley — a female prime minister and a global role model who leads with empathy, intelligence and strength.

Shelly-Ann Fraser-Pryce – Pocket Rocket! A young woman who showed the world that being a mom does not stop you from achieving your dreams! A symbol of perseverance and excellence who continues to inspire and give back across generations in her country.

Nanny of the Maroons – a fearless leader who exemplifies resilience and resistance.

SO: How would you describe Sheraley in a few sentences?

SB: Sheraley is a fun-loving, dynamic, purpose-driven leader who brings vision and heart to everything she does. Grounded in integrity, she believes in uplifting others while pursuing meaningful impact in every sphere she touches.

SO: How would you describe your style?

SB: Timeless, eccentric, polished and confident. I love pieces that reflect elegance while allowing room for bold accents and personal flair.

SO:
What’s your must-have fashion essentials?

SB: A classic black dress, bold statement heels (my signature touch), an elegant evening bag and standout jewellery – pieces that instantly elevate any look.

SO: And your handbag essentials?

SB: A notebook (yes, I write down everything), purse, foundation, lipstick and my phone.

SO: How important is what you wear and how you look?

SB: What you wear and how you present yourself are incredibly important. They reflect not just your personal brand but also your respect for the occasion, the people you are engaging with and yourself. Appearance is not about vanity, it is about confidence, credibility and showing up as the best version of yourself. In a professional setting especially, your look speaks before you do. After all, you never get a second chance at a first impression! So I believe in dressing with intention and authenticity.

SO: What’s currently in the rear-view mirror for your personal life?

SB: The need for perfection and self-doubt. I have learned to embrace growth, trust my instincts and lead with courage, even in uncertainty.

SO: Which song is playing in your head? Why?

SB:
You Make Me Stronger by Kevin Downswell, because it is a reminder that every challenge brings growth and resilience. Its energising and powerful!

SO: An evening in or out?

SB: Life is about balance — I do love an evening in with my family as I value relationships, conversations and reflections. However a night out every now and then with friends is also very needed!

SO: What’s your preferred rum cocktail?

SB: Appleton Signature and Coconut water.

SO: Finally, what’s your philosophy?

SB: Live with intention allowing God to guide your every step. Lead with integrity and always send the elevator back down as you rise. True success lies in creating meaningful value, not just for yourself, but for those you serve along the way.

Sheraley Bridgeman (Joseph Wellington)

Appleton Signature Single Estate Jamaica Rum and coconut water (Joseph Wellington)

Kevin Downswell’s You Make Me Stronger stays on repeat….

Sheraley’s handbag essentials.

Nanny of the Maroons.

Mia Mottley.