In this episode, Alex & Annie sit down with Vinny Dicarlo, CEO of Ciirus, and Josh Parry, Chief Product Officer, for a conversation about the philosophy that has shaped the company over nearly two decades.

Founded as a family business, Ciirus has taken a deliberately measured approach to growth. Rather than building around outside investment or pressure to scale at all costs, Vinny and Josh explain how the company has focused on long-term customer relationships, continued investment in its technology, and human support that keeps the team closely connected to the property managers it serves.

That approach opens up a broader conversation about what operators should expect from a technology partner today. Vinny and Josh share why they believe there are limits to how much vacation rental operations can be automated, where AI can genuinely help, and why human involvement still matters in an industry where every property, owner, guest, and stay can look different.

Episode Chapters:

11:14 - Building customer relationships designed to last

17:15 - Why Ciirus has chosen measured growth over growth at all costs

18:28 - How independent ownership shapes investment in customers and technology

22:38 - Why vacation rental operations cannot automate everything

27:39 - Building a global team around specialized talent

32:49 - Helping property managers get more from their technology

38:14 - Why customer and employee satisfaction matter together

39:55 - Ciirus’ new mobile app, owner tools, and Booking.com integration

46:03 - How LoveRentals helps property managers expand their capabilities

54:59 - Finding vacation rental demand beyond the major OTAs

57:55 - Reaching guests through travel agents, wholesalers, and international markets

1:02:24 - What is next for the Ciirus platform

If you are evaluating your tech stack, thinking about sustainable growth, or looking for new ways to reach guests, this episode offers a closer look at what a strong technology partnership can bring to your business.

Connect with Josh & Vinny

Josh Parry: https://www.linkedin.com/in/josh-parry-47165997/

Vinny Dicarlo: https://www.linkedin.com/in/vincenzo-dicarlo/

Connect with Ciirus

Website: https://ciirus.com/

✨ Exclusive Offers to Alex & Annie Listeners:

Alex & Annie listeners can receive their first three months of Ciirus subscription fees waived when joining the platform.

Visit https://ciirus.com/ and let the team know you heard about Ciirus through the Alex & Annie Podcast.

Thinking about the next chapter for your vacation rental business?

Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

👉 Learn more: https://gomonarch.com/partnerships/

List your professionally managed properties on VacationFinder.com with no listing fees or booking commissions.

👉 Get started: https://partners.vacationfinder.com/alexandannie

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