vacation-rental
(3)
Dustin Downing
Dustin Downing is the CEO of Key Data, a short-term and vacation rental analytics company that turns property management system data into real-time market intelligence across hundreds of global markets. He stepped into the role in mid-2026 after joining as president, succeeding co-founder Jason Sprenkle. Downing spent nearly two decades in product leadership across travel and data-driven technology, including nearly a decade at Sabre, a stint at influencer commerce firm LTK, and six years scaling OrderMyGear. His focus at Key Data is deepening the company's proprietary dataset and building the AI-driven intelligence layer he believes the rental industry will run on.
Summer
Summer is a New York proptech company that builds SummerOS, asset-management software for short-term rental operators. After starting as an asset-heavy 'own a vacation home without the risk' model, the Airbnb-alumni team pivoted to SaaS, crunching market data and a property's own performance to tell operators exactly what to fix, raise, or rethink. It aims to bring professional-grade, data-driven tools - long standard in commercial real estate - to the fragmented $125B short-term rental market.
Vacatia
Vacatia is a hospitality company reinventing the timeshare experience. It runs a marketplace for buying, selling, and trading vacation ownership interests, and increasingly manages the resorts behind those interests - bringing modern booking technology and owner services to a category that hadn't seen much of either.