This year marks a major milestone for Sentry Insurance Brokers – 20 years of protecting what matters most for individuals, families, and businesses across Barbados and the region. Founded in 2005 by Stephen Olivierre and Allan Kelly, Sentry was built on a simple but powerful vision: put the client at the center and deliver insurance solutions with integrity, efficiency, and care.
From those early days, Sentry quickly grew to become one of the island’s top three brokerages, standing proudly alongside century-old competitors. Today, strengthened by regional partnerships and global affiliations, Sentry provides coverage for leaders in construction, hospitality, transport, healthcare, and beyond,while continuing to serve individuals and families with the same personal touch.
What Makes Sentry Different?
Unlike insurance agents who represent one company, Sentry is an independent broker, meaning it goes to multiple insurers to design the best protection for customers’ unique needs. Whether you’re a small business owner, a homeowner, or a major corporation managing complex risks, their job is to find the right fit, at the right price.
Innovation at Work
Over the years, Sentry has embraced digitisation, automation, AI, and cybersecurity to deliver smarter, faster, and more secure service. Their upgraded systems mean client information is always at their fingertips, allowing a quick response time, while protecting data with the highest standards.
More Than Business
For Sentry, success has always been about people. From sponsoring the champion Deacons Women’s Volleyball Team, the Sentry Rockets Hockey Team, and the Sentry Glassesco Cycling Team, to supporting schools, churches, Verdun House, and the Barbados Cancer Society, the company believes in giving back to its communities.
Award-Winning Service
Their dedication hasn’t gone unnoticed. In 2014, they proudly received the Barbados Small Business Association Award for General Services, recognition of the high standards that remain the cornerstone of the company today.
Looking Ahead
As Sentry celebrates two decades of service, they are looking to the future with bold ambition: to be the most trusted, innovative, and client-empowered insurance partner across Barbados, the Caribbean, and beyond.
To their clients, staff, and partners, thank you for being part of their journey. Here’s to the next 20+ years, stronger together!
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