Josh Parry & Vinny Dicarlo

Josh Parry & Vinny Dicarlo Profile Photo

Managing Partners at CiiRUS STR Software

Josh Parry and Vinny Dicarlo are the Managing Partners of CiiRUS Short-Term Rental Software, a platform built by people who have spent their lives in the vacation rental industry.

The company was founded by their fathers in 2008, and today Josh and Vinny lead it with the same hands-on, family-run mindset. They believe hospitality is personal, and the software behind it should be too.

Vinny leads operations and growth, staying closely connected to customers and making sure the company stays approachable and grounded as it scales. Josh focuses on product and marketing, working closely with property managers to shape a platform that actually fits how their businesses operate.

Together, they spend most of their time listening to managers, solving real problems, and building tools that help teams grow without losing what makes their business work in the first place.

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Sept. 16, 2026

Building Vacation Rental Tech for Customers, Not Investors with Vinny Dicarlo and Josh Parry of Ciirus

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 te...