On October 7, 2025, Sentry Management will proudly celebrate its 50th anniversary, marking half a century of serving communities! What began in 1975 as a small team in Central Florida has since grown into a locally focused, nationally recognized community management company spanning more than 20 states. As the company reflects on its formative history, Sentry remains committed to supporting communities, boards, and homeowners nationwide with the same dedication and service standards that defined its earliest days.

Sentry’s Growth

Sentry’s story has always been one of growth and adaptation. Starting in Orlando with a handful of accounts, Sentry steadily expanded throughout Florida and, by the late 1990s, began opening offices across the Southeastern United States. From Kissimmee and Fort Myers in Florida, then to Atlanta, Phoenix, and beyond, Sentry grew by forming lasting partnerships and implementing a centralized support model that ensured consistency and quality across its operations. These strategic moves not only expanded the company’s local reach and strength but also built the foundation that now allows Sentry to support communities nationwide.

Since 2015, Sentry has doubled in size, expanding into numerous states and communities nationwide. Today, the company operates in over 20 states, serves 3,200 homeowner associations and condominiums, and employs more than 1,100 staff members. With this continued growth, Sentry Management remains one of the longest-standing management companies in the industry and one of the few operating on a national scale.

The History & Meaning Behind This Milestone

This anniversary is more than just another milestone – it symbolizes decades of resilience, dedication, and the trust placed in Sentry. Throughout the years, Sentry’s mission has remained the same: embracing the honor to serve and nurturing communities we are all proud to call home.

When a fire destroyed Sentry’s office in the 1980s, the company’s early adoption of digital record-keeping helped it recover and move forward despite the setback. Soon after, founder Jim Hart brought in Howard Pomp as a partner and investor, marking the start of a new era of growth beyond Florida.

Since then, key milestones have continued to shape Sentry’s journey while reflecting its core values: launching our charitable giving program, Giving Smiles, in the mid-2000s; developing and launching CommunityPro®, our proprietary association portal software, in the 2010s; creating an employee hardship program in 2023; and earning recognition as a National Top Workplace in 2024 and 2025. Each step shows how, even as Sentry has grown and evolved over five decades, its mission and values remain steady.

As Sentry celebrates this milestone, its Promises—a set of cultural guidelines and service commitment standards—and Foundation Principles—the values that drive all employees to operate in the best interests of communities with reliable, professional, and simplified services—position the team for excellence in the decades ahead.

Moving forward, Sentry carries with it the experiences, principles, and Promises that have shaped its past while embracing the honor of serving communities with innovation, stability, and growth in the years ahead. With gratitude for the journey that led to this milestone and excitement for what’s to come, Sentry Management remains committed to helping communities thrive.