Hate Your Boss? Use Hipmunk’s “Spite” Feature To Book His Travel

Why the travel search engine is targeting frustrated assistants in its bid to become the go-to source for business bookings.

Hate Your Boss? Use Hipmunk’s “Spite” Feature To Book His Travel


A new feature on travel search engine Hipmunk gives business travelers the worst possible experience. On purpose.  

The Kayak competitor’s main mission is to deliver the best flight results based on a combination of price, duration, and layovers (with the least “agony” in Hipmunk parlance). But starting today, Hipmunk Business Class launches with a “spite” feature that sorts flight options and ranks the worst possible travel experience first. It’s a tiny but telling feature in Hipmunk’s new product for business travel.

For $10 per month (the first 60 days are free), the service will send travelers flight and hotel options for approval, automatically update an Outlook or Google calendar with travel plans, and save individual travel preferences in one spot.

Unlike other services that appeal to company budget crunchers and decision makers, however, Hipmunk’s approach to business travel targets the people who actually book it. It’s hoping to slip into the enterprise market through frustrated executive assistants.

“We’re still marketing and selling as a product for individuals,” Hipmunk CEO Adam Goldstein tells Fast Company. “The strategy is to go after assistants who might put it on their company card or buy it themselves because it’s useful.”

That’s where the spite rankings come in. “Is
the boss making you angry?” asks pop-up text when you scroll over the option. “Make him suffer!” It’s pretty clear who the intended audience is.


Pursuing business travelers via their assistants pits Hipmunk against a new set of competitors. In addition to competing with Orbitz, Kayak and other travel aggregators, it will now also compete with travel agencies such as Egencia and Carlson Wagonlit Travel as well as offshoots of those competitors like Orbitz for Business and Travelocity Business.

Hipmunk’s business booking option is not as robust as some
of its competitors (it does not, for instance, offer booking assistance, preferred rates or expense management tools) but its practical offerings target companies that may not otherwise pay for business travel management tools–and the employees who actually use them.

“We’re not thinking of it as an enterprise product,” Goldstein says. “We’re thinking of it as a consumer product that happens to be used by people in enterprise.”



From the archive: Adam Goldstein and Reddit cofounder Steve Huffman created Hipmunk, a combination airline ticket search service and aggregator, to take the “suckage” out of planning trips.



[Image: Flickr user Natalie Downe]

About the author

Sarah Kessler is a senior writer at Fast Company, where she writes about the on-demand/gig/sharing "economies" and the future of work.