Whimstay to Accelerate Growth and Innovation in 2023, Starts by Appointing David Weiss CEO

Travel can be thrilling, but there are plenty of logistics issues to worry about if you decide to go on a last-minute vacation or need to take a trip on a moment’s notice. Whimstay helps ease the burden of spontaneous travel–and even rewards you for it–by offering up to 60% off last-minute vacation rentals, allowing customers to Seize the Stay. And this is just the beginning. Whimstay is poised to expand its offerings in the coming year, with many new developments in the works, starting with announcing the company’s new CEO.

David Weiss becomes CEO: As of today, the Board of Directors has appointed David Weiss, formerly serving as COO, as Chief Executive Officer and member of the Board of Directors. He will replace former CEO and founder Ben Jamshai, who will retain his position as Chairman of the Board.

According to Jamshai, “David has proven in his short time with the company that he is the ideal person to craft the vision and execute the path forward for Whimstay.”

Jamshai continued to say that Weiss brings “vacation rental marketplace, software, property manager and owner experience” to the table and that he has demonstrated “strong leadership traits, good judgment, and resilience while being a team-builder and a tough-minded competitor.”

Weiss brings years of experience: In the last ten years, Weiss has led teams that built and operated Vrbo’s end-to-end payments experience. During that time, he oversaw onboarding and delivery of payouts to roughly one million property owners across North America and Europe while offering payment methods and support to travelers worldwide.

• Weiss’s teams launched fraud prevention, chargeback management, compliance, and licensing services.
• Teams under Weiss established integrations with all the major vacation rental software companies.
• His company processed over $10 billion in annual payments volume for vacation rental owners and property managers worldwide.

Before the operational roles above, Weiss held a career in investment banking, which spanned 20 years. But he is excited about the future, stating that today’s CEO announcement “represents the greatest honor” of his career.

Whimstay has big plans for 2023: Weiss’s appointment is only the start of what Whimstay has in store for this year. The company’s plans include expanding its services, allowing travelers to book deals on vacation rentals during shoulder seasons, off-seasons, pre and post-holiday periods, and weekdays leading into weekend getaways at popular destinations.

• Whimstay will continue to provide top-notch last-minute booking services.
• The primary goal of Whimstay is still enhancing the traveler experience by offering the best last-minute deals on rental properties that might otherwise go unbooked.
• For property managers and owners, Whimstay’s mission is to attract incremental travelers and generate incremental bookings, thereby increasing occupancy rates and RevPAR.

Whimstay plans to announce strategic partnerships and new product features to benefit all parties on its platform, including guests, software partners, property managers, and owners. 

In the words of Whimstay’s new CEO, David Weiss, “The opportunity ahead for Whimstay is vast, but to seize it, we must focus, get stronger, get smarter, and move faster, so that guests can Seize the Stay!”