The DeWinter Difference with Dave Stephenson, Chief Business Officer and Head of Employee Experience at Airbnb

About The Episode

In this episode of the DeWinter Difference, Derek sits down with Dave Stephenson, Chief Business Officer and Head of Employee Experience at Airbnb. Dave shares his incredible career journey, from being a ski racer and aspiring architect at Montana State, to roles at Procter & Gamble, Amazon, and his current position at Airbnb.

They discuss the importance of gaining deep functional skills, the value of mentorship, and the critical role Airbnb played as an Olympic sponsor. Dave also offers advice for aspiring leaders and reflects on his own experiences, including teaching skiing and what he’s learned hosting on the Airbnb platform.

Chapters:

0:00 Intro

00:30 Meet Dave Stephenson: From Amazon to Airbnb

01:05 Dave's Early Career and Education

02:35 Transition to Amazon and Joining Airbnb

04:26 New Role at Airbnb and Leadership Insights

07:20 Advice for Aspiring Leaders

10:36 Airbnb's Role in the Olympics

14:44 Personal Experiences with Airbnb

18:41 Future Aspirations and Final Thoughts

About Dave Stephenson:

Dave Stephenson is responsible for growing Airbnb’s global businesses and overseeing Airbnb’s employee experience. As Chief Business Officer, he is focused on commercializing Airbnb’s new and existing businesses, recruiting and developing Airbnb’s global supply of stays, Experiences, and services, and executing Airbnb’s global in market strategy. As Head of Employee Experience at Airbnb, he oversees talent and leadership development, recruiting, compensation, diversity initiatives, and Airbnb’s Live and Work Anywhere program. Dave previously spent five years as Airbnb’s Chief Financial Officer.

Prior to joining Airbnb, Dave spent 17 years at Amazon, where he was Vice President and CFO of their Worldwide Consumer Organization. Dave also served as CFO of Amazon’s International Consumer business and led finance across many areas of the company, including Amazon Web Services, North America Retail, and Merchant Services. 

Dave holds an MBA from the University of Iowa and a BS in Industrial and Management Engineering from Montana State University. He is an Airbnb host in Washington State.

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