Jakob Dwyer
CEO
Jakob Dwyer is the CEO of Awayday and a longtime leader in the vacation rental industry. Prior to Awayday, he helped grow RealJoy Vacations into a successful high-growth company, gaining firsthand experience in operations, business development, and what it takes to scale without losing the local strengths that make a business work. Today, he leads Awayday’s continued growth with a focus on local leadership, strong operations, and long-term value.
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April 7, 2026
How Awayday Is Scaling Without Losing Local Identity, with CEO Jakob Dwyer
Send us a message! What does it take to grow a vacation rental company without losing the local identity that made it successful in the first place? In this episode, we are joined by Jakob Dwyer, CEO of Awayday, to talk about how the company is scaling through a model built on local leadership, shared support, and strong operational foundations. Instead of forcing every market into the same mold, Awayday supports growth through shared resources across accounting, HR, revenue management, business...
Guest: Jakob Dwyer