15 Frequently Asked (& Answered) Questions About Upside

We get it. We’re the new kids on the block and you have lots of questions about who we are, what we do and why we’re here.

To shed a little light on what we’re starting up over here at Upside, we’ve pulled together the top 15 frequently asked questions about Upside.

1. WHAT IS UPSIDE?

Upside is a brand new way to buy international business travel from Priceline’s founder Jay Walker. We create package deals to reduce travel costs for your company, while giving you lots of free gift cards when you agree to be a little bit flexible on things that don’t affect the business needs of your trip. You can learn a little bit more about Upside here.

2. WHAT DOES UPSIDE “BETA” MEAN?

BETA | noun | be•ta

  • Nope, we’re not referring to the second letter of the Greek alphabet.
  • It means we’re just getting started and there’s a lot to come. As we’re in our initial stages of the Upside product, your site experience will get better every week, but rest assured the booking engine is ready for primetime. You can be fully confident that your flight and hotel plans (and gift cards) will be rock solid. You can sign up to be a VIP and be one of the first to try Upside Beta here.

3. WHAT KIND OF TRAVEL CAN I BUY DURING THE BETA?

While we’re in Beta, our focus is on international round trip travel departing from one of our five initial departure cities to more than 40 international destinations. We’re adding new cities all the time — so, you can expect to see one-way and multi-city travel shortly!

Upside Beta’s 5 Departure Cities

New York, Boston, Chicago, San Francisco or Los Angeles.

Upside Beta’s 40 International Destinations

Abu Dhabi, Amsterdam, Bangalore, Bangkok, Beijing, Berlin, Bogota, Brussels, Buenos Aires, Copenhagen, Dubai, Dublin, Frankfurt, Geneva, Hong Kong, Istanbul, Johannesburg, Kuala Lampur, Lisbon, Madrid, Manila, Mexico City, Moscow, Mumbai, Munich, Osaka, Paris, Rome, Sau Paulo, Seoul, Shanghai, Singapore, Stockholm, Sydney, Taipei, Tel Aviv, Tokyo, Vienna and Zurich.

4. WHY DOES UPSIDE ONLY SELL AIR + HOTEL PACKAGES?

You probably know that “package deals” save money. That’s why we only sell air and hotel packages for a single, combined price. Package pricing allows airlines and hotels to give us unpublished discounts because we never reveal the individual prices.

5. HOW ELSE DOES UPSIDE REDUCE TRAVEL COSTS?

Upside is not like any travel provider you’ve seen before. We use a revolutionary new technology called a Flexibility Engine. It helps you discover how little bits of flexibility on travel arrangements can save your company money and get you free gift cards on every business trip you buy. Using Big Data and Cloud Computing software, it instantly analyzes the massive airline and hotel databases — including every flight, hotel and price — to discover and price travel options that work for you based on airlines and hotels you pre-approve. You can learn more about our Flexibility Engine here.

6. HOW MUCH IN GIFT CARDS CAN I GET?

The answer depends on the specific trip you’re taking and how much flexibility you have on that trip. We expect many of our customers, particularly those who are eligible to fly Business Class, will get $1,000 or more in gift cards on each international trip. You can learn more about our gift cards and view our growing list of top retailers here.

7. DO I SEE THE DETAILS OF MY PACKAGE BEFORE I BUY IT?

Of course! We will always show you the exact flights and hotel in your package before you have to buy a thing.

8. DO YOU REDUCE COSTS BY SELLING LOW QUALITY AIR/HOTEL?

We sell the same quality airline and hotel brands you use right now, as well as top-quality independent hotels that are not part of any chain. With Upside, you’re always in control. You will always see the exact same brands you are getting before you purchase your Upside Package.

9. WHAT DO I DO IF I NEED TO CHANGE OR CANCEL MY PLANS?

We get it. Business travel plans change constantly. Changes or cancellations are no problem. We have a team of Navigators ready to assist you 24/7 by phone, email, chat and social — before, during or after your trip. For any inquiries please call them at (855) 252–2151 or email at navigators@upside.com.

10. WHEN DO I COLLECT MY FREE GIFT CARDS?

Your gift card account is credited within 72-hours of an Upside package purchase. How you spend your gift cards earned from your trip is completely up to you! You can learn more about our gift cards and view our growing list of top retailers here.

11. WILL I STILL GET MY FREQUENT FLYER MILES?

Yes! When you buy your business trip with Upside you still get all the frequent flyer miles you’re entitled to.

12. ARE THERE TAX IMPLICATIONS TIED TO GIFT CARDS?

We have been advised that gift cards earned through Upside are similar to other promotional travel benefits like hotel points and frequent flyer miles. But, we’re travel experts, not tax experts! So, we recommend you reach out to your tax advisor should you have any questions or concerns.

13. HOW DO I SHOW MY COMPANY THAT I SAVED MONEY?

Whenever you buy a business trip from Upside, we send you a detailed “Expense and Savings Report.” It details how much your Upside Package cost, and it shows how much comparable flights and rooms would have cost without Upside, based on available flights and rooms at the time of your purchase. Working from this comparison, we calculate the estimated savings for your company, both in absolute dollars and in percentage terms.

14. WHO DOES UPSIDE WORK BEST FOR?

If your company lets you pick your airline and hotel brands for yourself, and you like getting gift cards to popular national retailers, then Upside is for you.

15. WHY DO TRAVELERS NEED AN INCENTIVE TO SAVE MONEY?

Until now, there wasn’t a good enough reason for travelers to give up any comfort or convenience to save money if their companies were paying the bill. With Upside, travelers now have a reason to help make lower travel costs possible. Check out our blog to learn more.

If you do not find the answers to your questions above, you can always contact our Navigators that are waiting to help you at navigators@upside.com or by calling (855) 252–2151.


Learn more about Upside here.

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