Jesse Stein is the Global Head of Real Estate at Airbnb, a global travel platform that connects guests with unique places to stay and experiences worldwide. He joined Airbnb in 2020 and has played a key role in building partnerships that expand supply, from multifamily housing initiatives to hotel collaborations. Prior to Airbnb, Jesse was a Principal at KHP Capital Partners, where he invested in boutique and independent hotels. He also held senior roles at leading hospitality companies, including Kimpton Hotels, Wyndham Hotel Group, and Starwood Vacation Ownership.

In this episode…

Boutique hotels have always had personality, but getting that personality in front of the right traveler has been the real challenge. In a world dominated by massive brands and OTAs, how can independent properties compete without losing what makes them unique?

For Jesse Stein, a longtime hospitality investor and operator, the answer lies in rethinking distribution entirely. He believes independent hotels don't need to outscale big brands. Instead, they need to lean into their strengths and meet guests where they already are. Jesse points out that success isn't about one channel or tactic, but about combining data, storytelling, and access to demand in a way that unlocks hidden value. Ultimately, it's about shifting from trying to compete like everyone else to competing in a way that actually fits the property.

In this episode of The Lights On Podcast, Kin Sio and Keri Brown are joined by Jesse Stein, Global Head of Real Estate at Airbnb, to discuss redefining hotel distribution for independent and boutique properties. They explore how Airbnb is evolving beyond homes, what independent hotels can learn about competing at scale, and how storytelling impacts conversion. Jesse also discusses the future of hotel partnerships and distribution strategies.