Building Agile Teams

Travel Goes Agile

How Booking Holdings saved Priceline and became the future of travel

Any experienced traveler knows the value of flexibility and fast action. Travelers are often required to make, break, or change plans at a moment’s notice, and the traveler who reacts quickly is the one who nabs half-price flights, discovers little-known destinations, and gets tickets to sold-out Broadway musicals. 
Those same values have been intrinsic to the runaway success of the online travel industry’s biggest players, and, both part of parent company Booking Holdings. Now responsible for almost 40 percent of the online travel industry’s market share, far ahead of next-in-line Expedia’s 18 percent, Booking Holdings attributes much of its success to an agile work culture rooted in the company’s early days of radical innovation.  
Embracing the radical
“Our success was founded on a single, radical new idea. We want an environment that honors this legacy by encouraging individuals and teams to simply ask "Why not?’” begins the Priceline website’s company culture page for potential employees. “We want employees who continually challenge themselves to look at things differently, seek a better way, and know they have the freedom to do so. That’s how we have succeeded, and that’s how we’ll continue to improve.”
A similar culture of innovation has been central to the success of since the company’s founding. Written on the walls is the simple slogan: “Get things done today. Tomorrow will bring fresh challenges.” Founded in Amsterdam in 1997, the company considers agile such a cornerstone of company culture that employees go through an Agility Boot Camp upon first joining the company. 
“Part of running a successful team is getting out of their way,” says Priceline founder and serial entrepreneur Jeff Hoffman, co-author of Scale: 7 Proven Principles to Grow Your Business and Get Your Life Back (with David Finkel; Portfolio, 2014). “As a leader, my job is to create an environment in which people smarter than me will run the company for me and never leave.”
Hoffman, who has won renown as an international mentor and speaker (TEDx, C-Suite Network, StartupGrind), presents a plan for creating an agile company that can grow based on the gifts and independent leadership of its workforce. In this context, he says, a leader’s job is to find the right people and train them in independent decision-making, then step back. “Do whatever you can to clear the path for their achievement,” Hoffman tells his fellow leaders in underscoring this idea. “You win when they do.”
The pivotal importance of pivoting
Priceline wasn’t always the success it is today, however; in fact, the company came close to becoming a casualty of the early dot-com boom and bust. Over those two years, Priceline’s stock price went from a high of $752 following its IPO in 1999 to hit a low of $7.69 by 2001, almost causing NASDAQ to delist the company. And for the next three years it bounced around in the single and double digits, again hitting a low of $7.50 in 2003. 
What saved the company was its ability to pivot, a flexibility exhibited both by Hoffman and his successor, longtime CEO Jeffery Boyd. Boyd’s smartest move, and the one that led to one of the most dramatic turnarounds of the decade, came with the 2005 decision to buy, an Amsterdam-based hotel booking site that was fast becoming a major player in European markets.
The acquisition gave Priceline instant international stature and positioned the company to better handle economic fluctuations and their tendency to rattle travel markets. This flexibility proved essential to the company’s survival when the terrorist attacks of 9/11 sent the domestic travel industry into near-collapse. 
In February 2018, the company acknowledged the central role of by changing its name from The Priceline Group to Booking Holdings and its stock ticker from PCLN to BKNG. While the company, which also includes under its umbrella,, OpenTable, Momondo, Cheapflights and, is based in Norwalk, Connecticut, almost 90 percent of the company’s 2017 revenues were made outside the United States. 
Agile culture as a cornerstone
All that growth – and the encompassing of more than eight distinct companies and platforms, comes with its challenges. And agile has been a significant factor in the conglomerate’s ability to survive and flourish in the face of so much change.
At, a cadre of agile coaches lead Agility Boot Camps designed to “lay the foundation for teams to collaborate and quickly adapt to unforeseen challenges,” says coach Melanie Wessels, who oversees the Agility Boot Camp program for incoming employees.
“Training prepares employees to work in short iterations before stopping to reflect on each work cycle,” Wessels says. “These ideas are then implemented in the next work cycle, allowing teams to innovate as they go.”
While Booking is most often cited as the ultimate agile workplace, Priceline isn’t far behind. A recent perusal of Priceline jobs listed on Glassdoor found "familiarity with Agile and Scrum methodologies” listed as a requirement for all positions.
Agility training isn’t just aimed to increase worker productivity, it’s a cornerstone of company culture. “Our employees look at life differently, have different values, and come from different backgrounds and cultures,” says Wessels, who has been afeatured speaker at OKR Forum in Amsterdam and at Agile Meetups. “As coaches, we don’t tell them to just accept each other and communicate better. We create an environment in which people can learn from one another, be their best selves and do their best work.”
Handling the workload
The sheer size and complexity of Booking Holdings today underscores this need. As of 2017, employees numbered close to 23,000, up from 18,500 in 2016. Of those, 17,000 work for Booking, and are spread over 198 offices dispersed across the globe.
The volume of work is equally enormous, with managing almost 30,000 properties worldwide, from resorts and hotels to Airbnb apartments, and booking 1,500,000 rooms a night. By the numbers, Booking Holdings is more successful than many better-known companies, including Apple and Amazon. The company’s stock price has risen an eye-popping 1500 percent over the past decade, leading to a market value that crossed the 100 billion mark this past summer. 
Underlying that growth is a customer-centered culture where “fail fast, learn fast” is a way of life. Agility training stresses collaboration and humility, with employees coached to admit when they don’t know something and ask for help.
“A humble culture creates an environment of psychological safety in which people aren't afraid of being wrong or making mistakes, and are free to innovate by taking chances. And this tends to result in great things," says Wessels.  “Going to work with a mask on doesn't help you or the people working with you. When we better understand why people may have certain communication gaps or other issues, our collaboration improves.”
These concepts are so central to the company’s mission that they’ve been articulated in a management philosophy officially known as Organized Chaos.
"Organized chaos means that employees are empowered to be innovative and extend beyond their comfort zones. That can mean challenging business as usual and trying something bold, surprising and completely new," says Wessels.
Failing fast, learning faster
In practice, employees describe a team-based system that draws heavily on Scrum and other agile tools and concepts but leaves the framework loose. “Each team is different and has its own spin on how to work together,” writes Product Owner Sarah Reiner in Booking’s online blog The Booking Way. “Some do strict Scrum with regular sprint planning meetings, managing one week, two weeks or longer sprints. Others have an open backlog that is only loosely prioritized, or decide what to work on next in ad hoc meetings. Some use a whiteboard. Others use some fancy software. I’ve seen color-coded Post-its with tasks scribbled on them hanging around. What counts is working together to achieve a common goal. You put in your best effort and strive to grow every day. No need for a uniform way of doing things.”
In her Agility Boot Camp trainings, Wessels emphasizes a process of continuous testing and iteration. “With the agile method, we can constantly test for the best outcomes, and tiny adjustments can be rolled back along the way if they don’t work as expected.”
Even more important is a willingness to think big and take big risks, to the point that teams have been known to have “failure parties” when an experiment doesn’t work.
“When teams set goals that stretch them beyond their comfort zones, they must approach projects differently than they have in the past, which forces them to think and act boldly and leads to greater innovation,” Wessels says.
Getting into the specifics, Reiner describes a workplace in which there are “virtually no rules,” with each employee controlling their own work environment, schedule, and priorities. “Simply put, there isn’t one way dictated by someone at the top. No one is telling you to do A, B and C, in that order, by the end of this quarter. We have the flexibility to decide for ourselves.”
Managers are hands-off, offering guidance but little overt direction. “We believe that the secret to true agile leadership lies in servanthood and humility. We train managers to understand that they’re not in charge, but instead are expected to guide and encourage,” says Wessels. “If you want to create an engaging, stimulating and empowering work environment, you need put the interests of your people at the center of what you do."
Agrees Reiner:  “Organized chaos means that you are empowered to extend beyond your comfort zone, follow opportunities, be innovative, be agile, and come up with what you believe will get us closer to bringing home the vision. That can mean to constantly challenge business as usual and to solve customer problems better. It can also mean trying something bold, surprising and completely new. The way you approach your work is up to you.”
All of this is directly in line with Hoffman’s Scaling principles, which focus on setting a business free to grow based on systematized operations, low-control leadership, and a workforce trained to execute freely. The goal: a company that’s proactive rather than reactive and that can survive the “hit-by-the-bus” test, meaning it continues to operate smoothly regardless of leadership changes. In other words, a company like Booking Holdings.
Of course, with the name and stock ticker change less than a year old and the travel industry landscape ever changing, the future of Booking Holdings is still unwritten. But with Fast Company deeming Booking the World’s Most Innovative Company of 2017 and the Economist calling them “maybe the best-run internet company after Amazon,” it seems clear there’s a bright future ahead for one of agile’s biggest corporate champions.