TripAdvisor’s Stephen Kaufer on Shifting from Founder to CEO

It all began with a trip to Mexico.

Like many travelers in 1999, Stephen Kaufer’s vacation began with a travel agent. Seeking recommendations on where to stay in Mexico, he left the agent’s office with three beautiful brochures for three gorgeous resorts at three distinct price points.

At the mercy of marketing materials that all painted a similar picture (“The brochures made each place look spectacularly beautiful.”), Kaufer initially considered booking the inexpensive option. Before putting down a deposit, he searched online for the cheap resort, hoping to uncover something more authentic than company- or travel agent-owned pages. He found a personal homepage—equivalent to a blog today—with a firsthand account of the resort, including photos. “It made me want to think twice about staying there,” he said. So, he booked the moderately priced resort, and had a great time on his trip.

“The decision process—searching the web to find what real people had to say about the resort—changed a very expensive purchase decision for me,” said Kaufer. “So, I thought, how can I turn this into a business?”

And, so, TripAdvisor was born.

As co-founder and CEO, Kaufer has been with the company throughout its 16-year journey from B2B vertical search engine to becoming the world’s largest travel site. Along the way, he has steered the company through pivots, sales, acquisitions and an IPO, to become an industry-leader in a highly competitive and rapidly evolving market.

Knowing When to Pivot

In its earliest stages, TripAdvisor’s model was business-to-business, meant to serve as a database of searchable travel information for consumer-facing sites such as Expedia and AOL to license for use. Though the product worked, it didn’t catch on, forcing Kaufer to rethink the company’s strategy and shift to a consumer-focused model.

“It’s funny to call it a pivot now. Back then, it was, ‘We have to do something different or we’re going to go out of business,’” recalls Kaufer. Though the pivot wasn’t voluntary, it ultimately proved profitable, paving the path for TripAdvisor’s dominance in the travel industry in the years that followed. “We changed, and what we landed on turned out to be a bigger business than anything we hoped for originally.”

Kaufer learned to accept change after his first brush with entrepreneurship as founder of Centerline Software. The company began as his independent software project in college and grew to experience early success, but “stuck to its knitting” rather than adapting to changes in the market and consumer needs. “It taught me to embrace the change.”

Today, TripAdvisor is continuously evolving. “We’re constantly looking at what we’re offering and trying to think of what the customer wants as opposed to what we do well,” said Kaufer. “That keeps us cutting edge and ahead of where our travelers want to be.”

Cultivating and Maintaining a Culture of Speed

In 2004, TripAdvisor sold to InterActive Corporation (IAC, the parent company of Expedia) for $210 million in cash. In 2011, it spun out as an independent, publicly traded company. Kaufer has remained onboard through it all.

“I looked at acquisition and asked, am I still able to drive a problem to solution? Or, did someone strip away that responsibility?” he said. “So, when TripAdvisor was acquired, I asked what they [IAC] wanted me to do differently. And, the answer was nothing.”

That freedom enabled TripAdvisor’s day-to-day operations to remain largely the same, and gave Kaufer the room to continue to grow the company at the rapid pace it set as a startup in spite of its size. “If you had asked me 15 years ago if I wanted to work at a 3,000+ people company, I would have said, ‘No, they’re way too slow.’ But, here we are.”

The opposite of slow, TripAdvisor maintains what Kaufer calls a culture of speed. “Our culture is we’re just going to move. We don’t want to be locked into a process that’s going to slow us down,” he said. That speed enables the team to release small patches of software on the site every day, and release new features every week. “That sets a mindset. Everyone knows it’s on that cadence all the time.”

As TripAdvisor continues to evolve, Kaufer’s goal is for it to become more than just a review site. “We want to be thought of as a great place to plan, book, and have a great trip,” he said. This ultimately means a shift in consumer behavior from using the site for research to using it to research, book, and plan every aspect of a vacation. “Where you’re going, where you’re staying, what you’re doing when you get there, what you’re going to eat, how you’ll get around—it’s all of those pieces.”

Proud Moments

During his time at the helm of TripAdvisor, Kaufer has earned a slew of awards and recognition for his entrepreneurship and leadership; this fall, he’ll be inducted into Babson College’s Academy of Distinguished Entrepreneurs^®. But if you ask Kaufer what he’s most proud of at TripAdvisor, it won’t be the accolades. Rather, it’s how the company has given back.

It gives back to their global community through a philanthropic arm, the TripAdvisor Charitable Foundation. Since 2010, the TACF has donated more than $20 million to nonprofits globally. “It’s our way of giving back some of the success that has been bestowed upon us.”

Second is that with TripAdvisor, everyone wins. By offering unbiased reviews from travelers, business owners learn what it takes to deliver a better product and fellow travelers find what they’re looking for when booking a vacation. “At our global scale, that’s a worldwide impact. And, I’m proud of that.”

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