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Protecting Families and Building Futures Across Trinidad & Tobago
For over 25 years, Dale McLeod’s Agency has provided reliable insurance solutions and career opportunities built on trust, strength, and integrity.
Industry Impact
2,500+
CLIENTS INSURED
25
TOP OF THE TABLE
MILLION-DOLLAR ROUND TABLE
11
GUARDIAN LIFE OF THE CARIBBEAN AGENCY OF THE YEAR AWARDS
The Promise Behind
Every Policy.
Insurance is more than protection on paper; it’s a trust you can count on when life takes an unexpected turn. For over 25 years, families and advisors across Trinidad & Tobago have turned to Dale McLeod’s Agency because we are grounded in three unshakable pillars: Financial Strength, Integrity, and Peace of Mind.
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We don’t just sell policies. We build partnerships, guide with honesty, and provide the assurance that you’ll never face life’s challenges alone.
Financial Strength
We are backed by decades of proven performance, regional recognition, and the stability of Guardian Life of the Caribbean. Your protection is built on a foundation that lasts.
Integrity
We believe in honesty, transparency, and always doing right by the people we serve. Every plan we design is tailored to your needs, never a one-size-fits-all solution.
Peace of Mind
At the heart of everything we do is reassurance. Whether you’re protecting your family, planning your retirement, or starting a career with us, we ensure you feel confident about the road ahead.
Our Story
In 1998, trailblazer and top producer Dale McLeod set out to build something different, an agency founded on relationships and a promise to put people first.
What began with one advisor and a clear vision has grown into a trusted agency serving thousands of families and advisors across Trinidad & Tobago. Our foundation has always been the same: Financial Strength, Integrity, and Peace of Mind.
For us, insurance is not just business; it’s about security and reassurance. It’s knowing your income won’t vanish overnight, your home will remain in your family’s hands, your children can pursue their future, and your retirement can be lived with dignity.
That’s why we go beyond transactions. We guide, support, and walk with you through life’s turning points, offering reliable solutions and lasting partnerships. Our mission is simple: to be the steadfast shield for what matters most, helping you protect your wealth, secure your future, and leave a legacy with confidence.
From the bustling heart of Maraval to the vibrant streets of San Fernando, our seasoned team stands ready to serve, committed to excellence, grounded in trust, and dedicated to people above all.
​How we protect
what matters most
We know that navigating life's complexities and risks can be daunting, but we are here to help. That's why our dedicated team is here to help you, by safeguarding what matters most.
Mortgage & Debt Cover
Integrity in protecting your home and commitments.
About Dale
Dale McLeod: a testament to discipline, tenacity, and generosity. He has dedicated his life to service, excellence, and mentorship. With over three decades of leadership, he stands as one of the Caribbean’s most respected figures in the insurance industry.
His achievements include:
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24-time Guardian Group Top Producer
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Recipient of the Chaconia Gold Medal for outstanding service to Trinidad & Tobago
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Mentor and guide to countless financial advisors who now lead successful careers
Dale’s leadership is rooted in his values: hard work, resilience, and a genuine commitment to people. These principles shape our agency and inspire every advisor on our team.
Build Your Career With Us
At Dale McLeod’s Agency, we believe a career in financial advising is more than a job; it’s a calling.
Our advisors don’t just work with numbers; they walk alongside families through the most important decisions of their lives.
When you join our team, you gain:
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Flexibility to manage your own schedule.
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Unlimited earning potential backed by Guardian Life.
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Comprehensive training and mentorship from Dale McLeod and other experienced leaders.
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A culture of support, growth, and shared success.
If you’re motivated, driven, and passionate about helping people, this is your opportunity to build a meaningful career with a lasting impact.
Client Stories
Our clients' satisfaction is our priority. Discover how we have tailored insurance options to suit their needs and provided reliable support during unexpected events.
Where Protection Meets Purpose
Insurance is not just a business to us—it’s a promise.
A promise to protect, to guide, and to serve with strength, integrity, and care.
Whether you’re looking to safeguard your family or build a career in financial advising, the first step starts here.
Two clear paths forward:
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Book a Free Consultation – let’s talk about your goals and create a plan that fits your life.
Join Our Team – take the first step toward a career that makes a difference.