Private Group Specialist- Sales

New York or Home Office


If you love international travel, why not turn your passion into a career! InsightCuba, a leading provider of people-to-people travel to Cuba for U.S. citizens is hiring for the position of Private Group Specialist. Work from our U.S. Headquarters in New York or from your home office.

Join us in ushering in a new era of travel for Americans and undisputedly the largest growing segment in the travel industry today.

As a Private Group Sales Specialist you will work with a talented and dedicated team providing group travel to Cuba for affinity groups. Private Group Specialists are responsible for responding to leads, prospecting, drafting proposals, negotiating and closing tours to clients. Domestic and Cuba travel is required from time-to-time.

Comprehensive training is provided and Spanish language is not required.


  • Respond to and prospect all leads including drafting proposals, following up, and closing.
  • Client management and providing top level customer service.
  • Achieving sales goals.
  • Work as a team, with Cuba Operations, U.S. Operations, and Sales departments.
  • Remain up-to-date on product information and be proactive in educating team members.
  • Travel may be required from time to time.


  • Proven track record in sales or group sales in the travel industry preferred.
  • Strong closing skills.
  • Having a ‘book-of-business’ is a plus but not required.
  • Energetic personality with great phone presence.
  • Excellent organizational skills, with the ability to multi-task and work under tight deadlines.
  • Passion for international travel.
  • Great problem solving skills.
  • Strong verbal and written communication skills.
  • Proficiency in Microsoft Office Suite, a CRM (Salesforce) and other digital platforms.


Compensation including salary and incentive is commensurate with skills and experience. Full benefits package after 90-days of employment includes: full medical, 401(k) plan, paid vacation, sick leave, and holidays. Other benefits include an all-expense paid trip to Cuba, and optional supplemental insurance coverage.


For consideration, please submit a letter sharing either, your most successful closing story or a professional accomplishment you are most proud of and your resume to Please put Private Group Specialist in the subject line.

InsightCuba is an equal opportunity employer and always employs qualified individuals based on job-related qualifications regardless of race, religion, color, gender, sexual orientation, marital status, national origin, age, disability, or any other classification protected under applicable federal, state, or local law.