Airbnb’s head of global hospitality and strategy Chip Conley shares his struggles and successes he experienced with the generational gap at Airbnb.

Having spent decades building up the second-largest boutique hotel group in the country from scratch, entrepreneur Chip Conley was a no-brainer hire for the then-fledgling Airbnb. But at 52 years old in 2013, the generational gap soon surfaced.

While Airbnb co-founder Brian Chesky was courting the hospitality expert, he offered to Uber to Conley’s home to discuss final details of his new position with the startup. The word “Uber” used as a verb caused some confusion.

“I said to him, ‘You’re going to do what?’” laughed Conley on Wednesday at the Internet Retailer Conference and Exhibition @ RetailX in Chicago. The self-proclaimed bricks-and-mortar guy had to confess his phone wasn’t exactly familiar with the app.

On the third day of his new job as Airbnb’s head of global hospitality and strategy, Conley found himself in a conference room surrounded by a dozen engineers who were half his age and making tech jokes that were going over his head.

“I had been brought into the company as a seasoned expert in my field, but in that particular room, I felt like a newbie amongst those tech geniuses, so I did my best to just be invisible,” he said.


While Conley was excited about the prospect of transforming a small tech startup into a global hospitality giant, he was reporting to someone 21 years younger. Moreover, he worried about his relevancy.

“I realized after my first week on the job with the kind of lingo that was being thrown around that my old-school, bricks-and-mortar wisdom wasn’t all that valuable in this new [online] world,” said Conley.

At a time when there are five generations occupying the same workplace, there can be tension and miscommunication. According to Conley, this is particularly an issue in the retail world, where bricks-and-mortar veterans might not have the digital fluency of ecommerce teams, yet younger employees may not have as much leadership experience. But he said the key is to tap into each group’s strengths and to create an “intergenerational pipeline of wisdom,” or a for employers to facilitate mentorship programs.

Conley, who spent four years in a full-time role at Airbnb and transitioned into an advisory capacity two years ago, said leveraging different skillsets of employees across all ages is necessary given the growing number of older people who are in the workforce and dealing with professional power shifting to young people. He cited a number of statistics that describe the landscape:

  • Nearly 40% of Americans have a boss who is younger than them, and by 2025, the majority of people in the workforce will be in that position.
  • The average age of an employee at a Silicon Valley tech giant is 30.
  • The fastest-growing demographic in the labor force is people over 60. That group showed a 35% growth in the last five years.
  • Between 2016 and 2026, almost half of the labor force growth will come from people 60 and over.

“The more I’ve thought about this, the more I realize that we, as different generations in the workplace often operate like isolationist countries,” Conley said. “We share a continent and borders but don’t share a common dialect or, frankly, point of view sometimes.”

To combat what Conley calls the irrelevancy gap, he counted on a 27-year-old coworker to be his digital intelligence tutor and would ask her to decode 16 different notes he’d scrawl down during meetings filled with technical jargon.

And in return, she gave him an epiphany. One day, she pulled him aside and told him his “fact knowledge”—such as knowing how many rooms a maid cleans in an eight-hour shift—doesn’t matter in the home-sharing world of Airbnb.

Instead, she told him the importance of his fact knowledge is “evaporating,” while his process knowledge is what’s valuable now, such as the best ways to motivate and communicate with fellow employees and keep them in the loop. Conley realized his organizational savvy was what he could offer.