Exclusive Insights from Whimstay’s CEO David Weiss on the Digital Executive podcast

David Weiss, CEO of Whimstay, the leading last minute vacation rental marketplace, recently shared his story on the Digital Executive. This podcast is hosted by Coruzant Technologies. In the podcast, David talked about his arrival at Whimstay and how the company has developed amazing technology and established strategic partnerships that enable Whimstay to offer exclusive discounts to travelers.

David joined Whimstay in August 2022, bringing with him an impressive career background. Prior to his work at Whimstay, David served as President at a travel and real estate payments business. Here, he led the company’s growth from $70 million to over $200 million in revenue during his tenure. He also launched an advisory business focused on Travel & Hospitality, FinTech, and PropTech, providing valuable services to marketplaces, OTA’s, SaaS businesses, private equity, and venture capital firms across a range of initiatives, including payments strategy, partnerships, product development, scaling operations, go-to-market strategies, M&A, and financing.

Before that, David worked as an investment banker for 20 years, covering the Fintech, Sustainability, and Diversified Technology & Industrial sectors. His vast experience in these sectors has enabled him to bring valuable insights and expertise to Whimstay, helping the company to grow and expand its last minute business model.

During the podcast, David also discussed the importance of luck and how it played a significant role in his career. He explained how he had applied to work at Whimstay on a whim, without any connections or introductions. However, his experience and skills impressed the team, and he landed the job.

David’s insights into the travel and technology sectors, along with his experience and skills, have been invaluable for Whimstay. With his leadership, the company has been able to establish strategic partnerships, and develop cutting-edge technology.

Whimstay commits to offer travelers the best deals on last-minute vacation rentals across North America. Whimstay also helps property managers and owners generate more profitability. David’s contributions have been instrumental in achieving this goal, and his story is an inspiration to others looking to make a career in the technology and travel sectors.

Click here to tune in and hear more from David about the future of Whimstay.

In this episode of the Digital Executive podcast, CEO David Weiss shares insights about the future of last minute travel.

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