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Sentry Management Top Workplaces USA TodayAt Sentry Management, our purpose is to nurture outstanding communities we are all proud to call home. Headquartered in the Orlando suburb of Longwood, Florida, with offices in 21 states, Sentry’s team of nearly 1,000 experienced professionals embraces the honor of serving our communities every day.

As we’ve grown over the last four decades to become one of the nation’s largest full-service management companies, we have never forgotten that our roots are always local, and our community always comes first. We proudly remain family-owned and values-driven, investing in our employees and the technology that supports them.

Sentry Management was recognized for its people-first workplace culture in 2022 and 2023 by the Orlando Sentinel Media Group as a regional Top Workplace and in 2024 by USA Today as a national Top Workplace. As a regionally and nationally ranked Top Workplace, our employees and the workplace are our main priority, and ensuring job satisfaction, fair pay and benefits, and employee engagement are paramount. We have a culture of ethics, trust, and teamwork that pushes us toward our goal of being the best community management company in the nation.

Positions are available for both Portfolio Managers and On-site Managers in offices located in Florida, Arizona, Colorado, Georgia, Idaho, Indiana, Maryland, Missouri, New Mexico, North Carolina, South Carolina, Tennessee, Kansas, New York, Iowa, and Virginia. Florida and Georgia community association managers must be licensed in accordance with State regulations.  Staff opportunities include Accounting, Accounts Payable, Accounts Receivable, Administration, Customer Service, General Ledger, and Operations, which are available in our Home Office located in Longwood, Florida.

Our Culture

Sentry has a strong culture of excellence. Our Foundation Principles are the backbone of our company and reflect the level of commitment, teamwork and spirit of continual improvement that our leaders and employees possess:

  • An enterprise goal of being the best community management company in the country
  • A core value of embracing the honor to serve our communities
  • A service standard of providing kindness, professionalism and timely resolution in every interaction.

We also have fun at work, hosting an annual Halloween costume contest, holiday decorating contests, multiple charitable donation competitions and drives, as well as many other events and celebrations to make the workplace enjoyable.

Investing in our Employees

We pride ourselves on promoting from within and providing our employees with room to grow and the tools and training they need to be successful.

Our training and development department provides high-quality in-house onboarding and ongoing training for Sentry employees. We maintain over 300 training resources and also offer a variety of live webinars each month.

Sentry’s annual Leadership Development Program invests in high-performing employees and creates a path to promotion into leadership roles.

Our education reimbursement program allows team members to pursue additional training and industry designations, as well as continuing education to support those team members who already maintain industry-specific designations.

Benefits, Rewards, and Recognition

Sentry offers a multitude of comprehensive benefits to our employees, including:

  • Medical, dental, and vision insurance
  • Disability insurance
  • Paid time off
  • 401K with matching
  • Employee Assistance Program

Sentry’s “Sen-sational Performers” program awards employees points for milestone anniversaries and for going above and beyond in their duties. The points can be redeemed for products, experiences or gift cards from an extensive catalog.

Giving Back

Sentry encourages employees to support the communities we manage through the company-wide charitable program known as “Giving SMILES.” The program identifies deserving residents that have been impacted by tragic events like fire, flood, or other personal hardships, and provides funding and assistance through company-matched and employee donations. To date, Sentry has helped over 450 families since the program’s inception in 2006. Sentry also supports 100 local charities and causes across 21 states and raises over $75,000 annually through events like a Central Florida charity golf tournament and as a national sponsor of the Arthritis Foundation’s Jingle Bell Run.

We are an Equal Employment Opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, national origin, disability status, protected veteran status, sexual orientation or any other characteristic protected by law. We celebrate and support diversity. 

Through UnitedHealthcare, UMR and HealthSCOPE Benefits creates and publishes the Machine-Readable Files on behalf of Sentry Management. To link to the Machine-Readable Files, please click here.

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