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Remote Sales Caribbean Jobs (NOW HIRING)

... and the Caribbean. Preference will be given to candidates who can work in EST or CST timezone ... Sales Leadership & Performance * Own and deliver the annual sales bookings target of $12M ...

... and the Caribbean. Preference will be given to candidates who can work in EST or CST timezone ... Sales Leadership & Performance * Own and deliver the annual sales bookings target of $12M ...

... and the Caribbean. Preference will be given to candidates who can work in EST or CST timezone ... Sales Leadership & Performance * Own and deliver the annual sales bookings target of $12M ...

... and the Caribbean. Preference will be given to candidates who can work in EST or CST timezone ... Sales Leadership & Performance * Own and deliver the annual sales bookings target of $12M ...

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Remote Sales Caribbean information

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$25K

$62.4K

$123K

How much do remote sales caribbean jobs pay per year?

As of Jul 4, 2026, the average yearly pay for remote sales caribbean in the United States is $62,441.00, according to ZipRecruiter salary data. Most workers in this role earn between $36,000.00 and $98,500.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a Remote Sales Representative in the Caribbean, and why are they important?

To thrive as a Remote Sales Representative in the Caribbean, strong sales acumen, market knowledge, and fluency in relevant languages are essential, often supported by a degree in business or related fields. Familiarity with CRM software like Salesforce, virtual meeting platforms, and digital marketing tools is typically required. Excellent communication, cultural sensitivity, and self-motivation are standout soft skills for building client relationships remotely. These abilities are vital for effectively reaching diverse markets, managing client needs, and consistently meeting sales targets in a remote environment.

What are some common challenges faced by Remote Sales professionals working with Caribbean clients, and how can they be addressed?

Remote Sales professionals serving the Caribbean often encounter challenges such as navigating diverse cultural expectations, managing time zone differences, and building trust without face-to-face interaction. To address these, it's important to develop cultural awareness, tailor communication styles to each client, and leverage virtual meeting tools to maintain regular, engaging contact. Proactive follow-up and a clear understanding of local market trends can also help build strong, lasting relationships with Caribbean clients.

What are Remote Sales jobs in the Caribbean?

Remote Sales jobs in the Caribbean involve selling products or services to clients while working from a location outside of a traditional office, often from home or any place with an internet connection. These positions typically require strong communication skills, proficiency with sales technology, and the ability to understand and cater to the unique needs of Caribbean markets. Remote Sales roles may include business development, account management, lead generation, and customer support, all conducted virtually. This flexibility allows companies to reach customers across various Caribbean islands and enables employees to work from anywhere.
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What states have the most Remote Sales Caribbean jobs? States with the most job openings for Remote Sales Caribbean jobs include:

$100K/yr

Other

Posted 11 days ago


Job description

Description

This is a remote, field-based position covering the state of Louisiana. You must be based inside the territory.


Do you want to earn $100,000+ working for a company with an incredible track record and sales culture? How about being part of a team that values independence AND teamwork? Do you have a passion for working with seniors, retirees, and frequent travelers?


MASA is currently seeking a motivated and experienced person with a background in outside sales leadership. You will work from home/virtual office, traveling to various locations within the state. Your goal will be to enroll and retain current members.


About Us

MASA has been a leader in emergency medical transportation insurance since 1974. 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.masamts.com


What You Will Do

Reporting to our Regional Vice President of Sales, you will develop and lead our sales team in your state. Your main responsibilities will include:

  • Recruit, develop, and train a new sales team of 1099 independent sales agents.
  • Lead the overall sales strategy, coaching, and development of the sales team.
  • Provide continuous feedback regarding individual and sales team progress.
  • Conduct sales seminars provided by the company as well as self-generate new leads and sales.
  • Coach on best practices for professional selling skills, effective supervision, and compliance.

What We Need From You

  • College Degree preferred.
  • 4+ years' experience and skills in leading and managing 1099 sales teams.
  • Previous and successful sales, leadership, and management experience.
  • Solid health insurance industry knowledge, preferably Medicare.
  • Strong sales management experience and analytical skills.
  • Proven presentation skills in group or seminar setting.
  • Exceptional interpersonal and communicative skills with both individuals and groups.
  • Driver's License (Required).
  • Insurance license NOT REQUIRED.

What We Will Provide You

  • Competitive base salary, bonuses, and comprehensive employee benefits programs.
  • 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!

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