Interview with Brian Chesky

Lenny Rachitsky, host of Lenny's Podcast and former Airbnb product leader, recently sat down with Airbnb co-founder and CEO Brian Chesky for a deep dive into the company's "new playbook." What unfolded was a candid, behind-the-scenes look at how Chesky radically re-architected Airbnb's product development, marketing, and leadership philosophy, offering a masterclass in founder-led product thinking and a stark departure from conventional tech wisdom.

Reimagining Product Management: Beyond the Buzz

The interview kicked off addressing the "elephant in the room": the widespread impression that Airbnb had eliminated its product management function. Chesky clarified that it wasn't about getting rid of people, but fundamentally transforming how they work together. He recounted speaking at Figma, where designers "started cheering" at the news, a reaction that highlighted a deep-seated frustration within the design community with traditional product development processes. As Chesky put it, "It wasn't the people, it's the way they're working together."

The core issue, he explained, was a growing disconnect where design often felt like a "service organization," catching errors rather than driving innovation. Many companies, he observed, build a great product but fail to connect it with the market. For Chesky, "you can't build a product unless you know how to talk about the product." This philosophy led to a significant shift: combining the inbound responsibilities of traditional product management with the outbound functions of product marketing. The team was made smaller, more senior, and tasked with managing by influence rather than control, forcing a new level of cohesion.

Key Changes:

• Combined product development (inbound) and product marketing (outbound) responsibilities.
• Offloaded program management tasks to dedicated program managers.
• Reduced the size and increased the seniority of the product marketing team.
• Designers and Engineers operate under a purely functional model, managing by influence.

A CEO's Return to the Details: Airbnb's Operational Overhaul

Chesky described a familiar cycle at many growing companies, including pre-pandemic Airbnb: an initial founder-led drive, followed by encouragement to delegate, leading to fragmentation, politics, and bureaucracy. By 2019, he felt the product was stagnating, costs were rising, and teams were spending "80 hours and getting 20 hours of productive work done." He realized that the more he delegated, the slower the company became. "The less involved I was in the project," he recalled, "the more spin there was, the less clear the goals... and the slower they moved."

The pandemic, which saw Airbnb lose 80% of its business in eight weeks, served as a "near-death business experience" that provided ultimate clarity. Inspired by conversations with Apple alums Hiroki Asai and Jony Ive, Chesky decided to run Airbnb more like a startup. He centralized control, pulling decision-making inward and establishing himself as the de facto "chief product officer." For a product- or tech-led company, he believes, "the CEO should be basically the chief product officer." This meant drastically cutting projects, removing layers of management, and shifting to a purely functional organizational model with fewer, more senior employees.

Key Practices:

• CEO acts as the de facto Chief Product Officer, deeply involved in product strategy.
• Shifted from a divisional structure (e.g., Guest team, Host team) to a functional model (Design, Engineering, Product Marketing).
• Removed layers of management to foster direct communication.
• Reduced the number of concurrent projects significantly.

The Art of the Launch: Story, Cohesion, and Purposeful Growth

Under this new model, clarity became paramount. Airbnb now operates with a single, rolling two-year product roadmap, updated every six months, with major product releases happening twice a year. Chesky also instituted rigorous "CEO reviews" for every project, a system that allowed him to stay deeply involved and identify bottlenecks without mandating specific solutions. He made a crucial distinction between "micromanagement" and "being in the details," arguing that "if you don't know the details how do you know people are doing a good job?" His involvement wasn't about telling people what to do, but understanding the work to ensure execution and alignment.

This approach also fundamentally reshaped their marketing strategy. Chesky introduced the metaphor of "lasers, flashbulbs, and chandeliers" to explain their shift away from an over-reliance on Performance Marketing (lasers) toward brand building (chandeliers) and education. Marketing, he explained, is about "educating people on the unique benefits" of new features, ensuring that when they "ship new things, people know about them or use them." They even built an in-house creative agency to ensure product and marketing are intertwined from the very beginning, with the story of a product often dictating its development. As Chesky reflected, "way too many Founders apologize for how they want to run the company... that's a good way to make everyone miserable because what everyone really wants is Clarity."

Key Learnings:

• Implemented a single, rolling two-year product roadmap with bi-annual major releases.
• CEO reviews ensure executive-level detail oversight and accountability.
• Distinguished "being in the details" from "micromanagement."
• Shifted marketing focus from pure performance to product education and brand building, with in-house creative.

Guest Favorites and the Future of Design: Airbnb's Winter Release

The ultimate manifestation of this new playbook was Airbnb's recent Winter Release. Chesky highlighted "Guest Favorites," a collection of the top two million homes combining Airbnb's unique inventory with the reliability guests expect from a hotel. This required a deeply integrated approach across guest experience, host tools, and market communication. Another significant update was a complete overhaul of the Host tab, previously a "hodgpodge thing" designed by disparate teams. This reflected a core belief: "to create a great guest experience you need great host and to have great hosts they need great tools."

The release also showcased a bold new design aesthetic, moving away from "flat design" towards a more "three-dimensional, colorful aesthetic" with light, texture, and playfulness, influenced by AI's capabilities and people's increasing time on screens. This holistic, cohesive approach, from a single roadmap to a unified brand voice, enables Airbnb to make bold bets like an AI-powered photo tour that organizes host images by room. These ambitious projects, Chesky asserted, "would not have been possible in the old way of working."

Key Insights:

• Product-led growth is driven by building exceptional products and educating users about them.
• Investment in host tools is crucial for delivering a superior guest experience.
• Airbnb is pioneering a new, more three-dimensional and tactile design aesthetic.
• Ambitious projects like the AI-powered photo tour require a highly integrated and cohesive operational model.

"if there's only one thing I said in this interview today... try to get everyone to row together in the same direction otherwise why the hell are you all in the same company." - Brian Chesky