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Upside is the new travel booking site from Priceline founder Jay Walker that launched publicly at the beginning of the year. Last summer I interviewed Jay about his history with Priceline and his new business idea.
They reward business travelers for saving their company money. Normally travelers book what’s most convenient within company guidelines because the employer is footing the bill. But connections, or a different hotel could save money. They offer savings to the employer and gift cards to the employee for taking cheaper options they can live with.
- Maybe you’ll fly in the night before if it saves more than the cost of a hotel night and they’ll give you $100 in your pocket to do it.
- Maybe you’ll stay at a hotel a mile away from the conference if it’s cheaper and they’ll give you $150 in your pocket to do it.
Upside asks the question, how much is your flexibility worth if there’s ‘upside’ to you? Are you willing to book a less expensive itinerary if you put money in your own pocket to do it?
They sell travel packages of flights and hotels, that way they can discount without running afoul of parity rules.
And usually this really is going to be for reimbursable business travelers, leisure travels should price flights separately, and hotels separately, and see how Upside’s pricing compares. And compare Upside’s packages to travel packages on other sites.
For both business and leisure travelers though they occasionally run compelling first-use bonuses like guaranteed gift card minimums that make booking through them a no-brainer.
Right now there’s a really interesting one: they’ll give first-time customers who purchase a minimum $600 trip by November 30th Bose SoundLink Around-Ear Wireless Headphones II (S230).
Upside tells me that their customer service investment is what’s actually moved the needle the most with independent travelers. If you call expedia you wait on hold interminably for outsourced agents who can’t help you. Upside built theirs around business travelers who expect concierge-level service, and it’s that service that keeps customers coming back rather than the rebates (though those are nice too).