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Pool​/Independent Travel Advisor​/Remote

Remote, USA Full-time Posted 2025-07-27

Position: : Work from the Pool/Independent Travel Advisor (Remote, Flexible, Fun!)
:
Work from the Pool/Independent Travel Advisor (Remote, Flexible, Fun!) :
Work from the Pool/Independent Travel Advisor (Remote, Flexible, Fun!)

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Owner/Travel Specialist @ Pennywise Travel | Leisure and Business Travel

About the Opportunity

Technology has evolved and so has travel! Pennywise Travel is looking for fun, motivated, and adventurous individuals to join our team as Independent Travel Advisors. If you love planning trips for friends, family, or yourself—why not earn industry-leading commissions and travel perks while doing it?

This is a commission-only opportunity, but with our industry-leading training, you’ll soon be “layoff proof,” making your own schedule, working from anywhere, and helping others make their travel dreams come true. No experience required—we provide all the tools, training, and support you need!

    Responsibilities
  • Maintain professional communication with clients and team members
  • Discover client desires, preferences, and budgets to create custom travel experiences
  • Research, organize, and book all travel arrangements (flights, hotels, cruises, activities, car rentals, tours, tickets, and more)
  • Build quotes, design itineraries, and finalize bookings
  • Stay up-to-date on travel trends, vendor updates, and safety protocols
  • Attend live or recorded webinars and trainings
    Requirements
  • Must be 18+ years old
  • Must have a dependable internet connection, smartphone, and computer
  • Ability to attend virtual trainings/webinars
  • Positive, can-do attitude and willingness to learn on your feet
  • Self-starter who works well independently but asks for help when needed
  • Fluent English required;
  • Spanish is a plus
    What’s in it for You?
  • 100% Remote:
  • Work from home, a coffee shop, or even poolside!
  • Ultimate Flexibility:
  • Be your own boss, set your own hours
  • No Experience Needed:
  • Full training provided, plus your Travel Agent Certification included
  • Free Business Website
  • Errors & Omissions Insurance with Fraud Protection
  • Commission-Only:
  • Unlimited earning potential
  • Free 3–30 day cruise for you and a guest after completing certain trainings
  • Heavily discounted rates on hotels, cruises, concert/sports tickets, tours, car rentals, and more
  • Discounted or free theme park tickets after vendor trainings
  • Work with top travel vendors:
  • Carnival, Expedia, Disney, and hundreds more!
  • Be Part of a $14 Trillion Industry!
  • Seniority level
  • Seniority level
    Entry levelEmployment type
  • Employment type
    Full-time
  • Industries Travel Arrangements

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