Navigating the intersection of design and business: a conversation with Airbnb’s Brian Chesky | Figma Blog

Airbnb CEO Brian Chesky argues that design should shape business strategy, not merely product appearance. He describes how Airbnb drifted from its design-led origins as it grew, becoming fragmented, experiment-heavy, and less innovative. By reconnecting with the principles of Apple’s design renaissance, Chesky began reconsidering how the company should be organized and led.

Pulling Airbnb Back from the Brink of Failure

• Airbnb was founded by two designers and an engineer, challenging conventional views that designers do not start companies.
• Its original philosophy was to bring design into the boardroom and create a product that felt distinctive and meaningful.
• By late 2019, Chesky feared Airbnb had become unrecognizable:
  • The company had roughly 10 divisions, each with numerous subdivisions.
  • Product managers and A/B testing dominated decision-making.
  • More employees and projects produced fewer visible product changes while increasing costs.
• Chesky believed he had lost the courage required for creative leadership and that conventional corporate practices had displaced Airbnb’s founding vision.
• The timing was especially difficult because Airbnb was preparing for its IPO, making major organizational changes risky.

Rediscovering Design-Led Leadership

• During the 2019 holiday season, Chesky met Hiroki Asai, a former Apple creative director, and Jony Ive, Apple’s former design leader.
• Their perspective reminded him of the design-centered culture Steve Jobs had established at Apple.
• Chesky began exploring whether Airbnb could return to a similarly integrated model, where design and creative judgment played a central role in how the company operated.

Design’s Place in Business

• Chesky suggests that designers are rarely elevated to CEO roles because businesses tend to favor scientific, analytical, and operational methods.
• Creative work requires conviction and risk-taking, qualities that can weaken as organizations become larger and more bureaucratic.
• His experience led him to question whether standard corporate structures are compatible with maintaining a company’s original creative vision.

The excerpt presents Chesky’s central lesson: sustained growth can dilute a company’s founding principles unless leaders deliberately preserve design, courage, and customer-centered decision-making at the heart of the business.