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.

 


Listen now at the streaming sites listed.


Learn more about the DeWinter Difference podcast here and share your thoughts and comments below.


DeWinter Named One of the Top 10 Best Places to Work in the Bay Area 2025
August 29, 2025
For the third year in a row, DeWinter has been named one of the Best Places to Work in the Bay Area by the San Francisco and Silicon Valley Business Times. We're honored to receive this recognition, which is a direct reflection of our incredible team and the vibrant culture we've built together.
Boston Finance & Accounting Careers: Your Guide to Strategic Networking
August 28, 2025
Unlock finance and accounting career growth in Boston. Learn expert networking tips to connect with top employers and recruiters in the Greater Boston Area.
Top In-Demand AI Job Titles and What They Mean for Hiring Managers and Candidates
August 26, 2025
Uncover top AI job titles in 2025, from ML Engineer to Prompt Engineer. Learn key skills for candidates and smart hiring strategies for managers.
The Complete Guide to Landing an AI Engineer Role in 2025
August 19, 2025
Unlock your AI career potential. This guide provides actionable steps—from portfolio creation to interview prep—to help you land your dream job as an AI Engineer.
2025 Mid-Year Boston Finance & Accounting Salary Guide and Industry Report
July 25, 2025
Navigate the dynamic 2025 hiring landscape with confidence. Our comprehensive 2025 Mid-Year Boston Finance & Accounting Salary Guide and Industry Report provides the data and expert insights you need to make informed career and hiring decisions.
2025 Mid-Year Bay Area Finance & Accounting Salary Guide and Industry Report
July 25, 2025
Navigate the dynamic 2025 hiring landscape with confidence. Our comprehensive 2025 Mid-Year Bay Area Finance & Accounting Salary Guide and Industry Report provides the data and expert insights you need to make informed career and hiring decisions.
2025 Mid-Year Southern California Technology & Digital Salary Guide
July 25, 2025
Explore DeWinter's 2025 Mid-Year Southern California Technology & Digital Salary Guide, your essential resource for navigating the evolving tech and digital landscape. Inside, you'll find comprehensive salary data for 67 top tech and digital roles, with precise local reporting for Boston, the Bay Area and Southern Ca
2025 Mid-Year Boston Technology & Digital Salary Guide
July 25, 2025
Explore DeWinter's 2025 Mid-Year Boston Technology & Digital Salary Guide, your essential resource for navigating the evolving tech and digital landscape. Inside, you'll find comprehensive salary data for 67 top tech and digital roles, with precise local reporting for Boston, the Bay Area and Southern California.
2025 Mid-Year Bay Area Technology & Digital Salary Guide
July 25, 2025
Explore DeWinter's 2025 Mid-Year Bay Area Technology & Digital Salary Guide, your essential resource for navigating the evolving tech and digital landscape. Inside, you'll find comprehensive salary data for 67 top tech and digital roles, with precise local reporting for the Bay Area, Boston, and Southern California.
The Heart of DeWinter: Living Our Core Values
July 24, 2025
At DeWinter, we often say that our greatest strength isn't just what we do, but who we are. We know that behind every successful placement, every strong client relationship, and every innovative solution, there are incredible individuals making it happen. Our team members aren't just colleagues; they're the embodiment