Whimstay CEO David Weiss

Whimstay announces Weiss as new CEO

US: Last-minute vacation rental marketplace Whimstay has announced the appointment of David Weiss as its new chief executive officer [CEO] and member of the board of directors, effective immediately.

Weiss, who previously served as chief operating officer [COO], will take over from Ben Jamshahi, the company’s founder and CEO since its inception. Jamshahi will, however, remain as chairman of the board.

Jamshahi said: “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. David has brought deep vacation rental marketplace, software, property manager and owner experience, as well as partnerships, capital raising, and M&A expertise to Whimstay.

“Beyond that, David is a team builder and a tough-minded competitor who has demonstrated over his career strong leadership traits, good judgment, and resilience,” he added.

Weiss said: “Today’s announcement represents the greatest honour of my career. Ben has built a great business with an amazing team and I look forward to partnering with him on the journey forward.

“The opportunity ahead for Whimstay is vast but, to seize it, we must focus, and get bigger, stronger, faster and smarter so that guests can Seize the Stay™,” he added.

Over the past ten years, Weiss has led teams that built and operated at Vrbo’s end-to-end payments experience, serving tens of millions of travellers globally, and over one million property owners in North America and Europe. He has also launched fraud prevention products, chargeback management, compliance and licensing services, and has established integrations with major vacation rental software companies.

Prior to that, Weiss spent 20 years in investment banking, advising CEOs, COOs, CFOs, boards of directors, and private equity and venture capital firms on capital raising and M&A across multiple industries, including the travel tech and proptech sectors.

In his new role, Weiss will be tasked with expanding Whimstay’s market offering beyond last-minute bookings, to include shoulder seasons, off-seasons, pre- and post-holiday periods, and weekdays leading into weekend getaway destinations. The company will also be making several announcements in the coming weeks regarding partnerships and key new hires.

He said: “Our core mission is to offer the best travel deals to guests, and for property managers and owners, attract incremental guests, and generate incremental bookings throughout the year. We’re excited about our plans to launch new products and features that enhance the guest and owner experience, with a focus on trust, affordability, flexibility, transparency, and safety.”

Whimstay currently offers homes, condos and more in 48 US states, Canada, and Mexico.

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