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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 development, and technology, while local teams continue to lead the day-to-day business. Jakob also shares how that approach influences the way Awayday evaluates partners, supports local operators, and balances growth with owner and guest experience.

This conversation offers a clear look at how Awayday is building scale through stronger operations and support without losing the local identity at the core of each business.

Episode Chapters:

00:00 - Intro to Awayday CEO Jakob Dwyer

01:14 - Jakob Dwyer’s background in vacation rentals and RealJoy’s growth

05:52 - How Awayday scales local vacation rental companies

10:50 - Why local market knowledge matters in vacation rental growth

13:07 - What Awayday looks for in a vacation rental partner

18:17 - Founder transitions, succession planning, and exit options

23:15 - Why strong vacation rental operations matter more than growth at all costs

27:01 - Awayday’s onboarding process and value creation strategy

31:41 - Shared services, local leadership, and centralized support

37:05 - How Awayday is thinking about AI in vacation rental operations

46:11 - SOPs, company culture, and empowering vacation rental teams

50:57 - Awayday’s growth strategy for 2026 and beyond

58:43 - Why every team member plays a role in company growth

This episode is brought to you by Awayday. If you are interested in being part of a company that values local leadership, strong operations, and long-term growth, connect with Jakob at jakob@awayday.com.

Connect with Jakob:

LinkedIn: https://www.linkedin.com/in/jakob-dwyer-19516033/

Connect with Awayday:

Website: https://www.awayday.com/
LinkedIn: https://www.linkedin.com/company/awayday-vacation-rentals/

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#vacationrentals #shorttermrentals #localidentity