David Weiss

CEO @ Whimstay

David Weiss is the CEO of Whimstay, a last‑minute vacation rental marketplace based in the San Francisco Bay Area; he was appointed CEO in January 2023 after serving as COO. He brings nearly 34 years of experience across fintech, travel & hospitality, proptech, and SaaS marketplaces — including leadership at Vrbo overseeing payments and fraud prevention, over 20 years in investment banking, and a BA in Political Science and Government from Harvard University — with expertise in strategic partner