Whimstay Announces David Weiss as New CEO

Former COO to Lead Travel Company Through its Next Phase of Growth and Innovation

SAN FRANCISCO, Jan. 11, 2023 /PRNewswire/ — Whimstay, Inc. is pleased to announce that David Weiss has been appointed Chief Executive Officer and member of the Board of Directors, effective immediately. Weiss, who previously served as Chief Operating Officer, will take over for Ben Jamshahi, the company’s founder, and CEO since its inception. Jamshahi will remain Chairman of the Board.

“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,” said Jamshahi. “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.”

Said Weiss, “Today’s announcement represents the greatest honor 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™!”

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 travelers globally, and over 1 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 most major vacation rental software companies, serving thousands of vacation rental property managers worldwide.

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 prop tech sectors.

In his new role as CEO, Weiss is looking forward to 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.

“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,” said Weiss. “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.”

Keep an eye out for David on the Alex + Annie Podcast, Paltrocast with Darren Paltrowitz, Where Next?, Travel with Kristen and Carol Podcast, as well as in Inc., Entrepreneur, Business Insider, CEO World, Grit Daily, and other publications in the coming weeks.

About Whimstay:

Whimstay is a vacation rental marketplace focused on providing travelers the best deals on trips while serving as the exclusive last-minute distribution partner for vacation rental property managers across the country. Whimstay was recognized as a Shortyz finalist for Best Online Travel Agency (OTA) in 2021 and Rentals United’s Who’s Who of new OTAs for 2020 and 2021. From beachside gems to ski retreats, to cozy mountain cabins, or to a desert oasis, Whimstay currently offers homes, condos, and more, in 48 U.S. states, Canada, and Mexico, and is adding new properties every day, and in new locations. Whimstay’s properties are available on whimstay.com and the Whimstay app.

Media Contact:
Tiffany Cummins
Talent Resources


SOURCE Whimstay