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A Remote Caribbean job allows you to work remotely while living in the Caribbean, either as a freelancer, remote employee, or digital nomad. These jobs typically require stable internet access and can range from tech and customer support roles to marketing and consulting. Many Caribbean nations offer remote work visas, making it easier for professionals to live and work legally.

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Infographic showing various Remote Caribbean job openings in Florida as of August 2026, with employment types broken down into 88% Full Time, and 12% Part Time. Highlights an 100% Remote job distribution, with an average salary of $39,128 per year, or $18.8 per hour.

Regional Sales Executive - Group Benefits

Medical Air Services Association, Inc

Miami, FL • Remote

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Re-posted 29 days ago

Job description

Description

This is a field sales position covering Florida


Are you an experienced Group Benefits sales executive looking for something fresh and different? Are you up for the challenge of educating brokers and groups on something new in exchange for a greenfield market with no competition?


MASA offers unique voluntary benefits products with strong strength-to-weight ratios. As our new Regional Sales Executive, we'll count on you to develop and manage key broker and consultant partnerships and grow a book of business.


About Us

Unexpectedly high charges for ground or air transport are an unfortunate reality in emergency care-even for the insured. Since 1974, MASA has been solving the devastating problem of high emergency transport costs.


We're not just a company - we're a close-knit team dedicated to "Protecting families with compassion when others don't." Our professional yet friendly company culture fosters collaboration, innovation, and a clear mission that resonates through every role as we support our expanding base of 2+ million members across the United States and the Caribbean. Learn more at https://www.masaaccess.com


What You Will Do

Partner with your territory's top benefits brokers to secure group agreements as a company-paid, or payroll-deducted benefit to eligible employees.


Your main responsibilities will include:

  • Making the market and owning the business in the defined territory.
  • Developing key broker and consultant partnerships.
  • Meeting and exceeding ambitious annual targets with a dual focus on growing total premiums and membership unit volume.
  • Creating effective group-specific sales and marketing plans.
  • Traveling regularly across the territory.

What We Need From You

  • 5+ years of Employee Benefits sales experience, preferably in voluntary/worksite, group life, or group disability insurance.
  • Currently based in the assigned territory with an active network of established brokers throughout the area.
  • Experience educating brokers about the need for unique products. Good at developing mindshare and getting partners to take a chance on something new.
  • Current A&H insurance license.
  • Demonstrated commitment to utilizing CRM technologies.
  • Proficient use of MS Office Suite: Word, Excel, PowerPoint, and Teams.

What We Will Provide You

  • Competitive base salary, commissions, bonuses, and comprehensive employee benefits programs, including medical, dental, and vision insurance with highly rated carriers; a 401(k) program with a company match; paid time off; company-paid short-term disability, long-term disability, and basic life insurance; and a free MASA membership.
  • A professional and friendly company culture that supports a clear mission: "Protecting families with compassion when others don't."
  • An opportunity to unleash your expertise and create a lasting impact on our journey of growth and success!

#LI-RH1 #LI-remote #B2Bsales

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