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 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 Dwyer01:14 - Jakob Dwyer’s background in vacation rentals and RealJoy’s growth05:52 - How Awayday scales local vacation rental companies10:50 - Why local market knowledge matters in vacation rental growth13:07 - What Awayday looks for in a vacation rental partner18:17 - Founder transitions, succession planning, and exit options23:15 - Why strong vacation rental operations matter more than growth at all costs27:01 - Awayday’s onboarding process and value creation strategy31:41 - Shared services, local leadership, and centralized support37:05 - How Awayday is thinking about AI in vacation rental operations46:11 - SOPs, company culture, and empowering vacation rental teams50:57 - Awayday’s growth strategy for 2026 and beyond58:43 - Why every team member plays a role in company growthThis 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 [email protected] 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/ ✨ Exclusive Offer to Alex & Annie Listeners:Streamline your short-term rental operations with Hostfully.Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value).👉 Click here to get started: https://www.hostfully.com/influencers/alex-annie/ Reach more guests across top travel sites with BookingPal.Alex & Annie listeners get onboarding fees waived + 20% off the first two months.👉 Click here to get started: https://alex-and-annie-offer.bookingpal.com/ #vacationrentals #shorttermrentals #localidentity

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