Eliminating payment chaos

Before Breezeway, managing payments for Oikos Property Management was entirely manual and often chaotic. Brendan and his team received messages from cleaners across multiple text threads, then scrambled to track down which jobs had been completed. Each vendor preferred a different payment method, ranging from Venmo and Zelle to PayPal, which meant Brendan had no central record of transactions. If questions came up later, he had to dig through messages and banking apps to confirm whether someone had been paid. As the company grew, this patchwork system became increasingly difficult to manage efficiently.

With Breezeway Payments, the process is entirely different. Each task is logged and tracked within Breezeway, and once a cleaner completes the job, the system automatically generates the record and initiates payment. Oikos no longer has to guess whether payments went out on time or whether work was completed to standard, the system ties everything together in one place. As Brendan explained, “Breezeway Operations first solved the record-keeping side for us… but the addition of payments made everything even easier for us. Now, once they complete the task, it automatically pays them.”

Saving valuable time and improving accuracy

Previously, managing payments consumed the bulk of Brendan’s workweek. He spent two hours every day reconciling invoices, confirming completed jobs, and processing payments. Even with all this manual effort, mistakes still happened, from double-paying a vendor to missing an invoice entirely.

Now, Breezeway automates the majority of this workload. Payments are set up to run directly from property-specific cards, ensuring accurate expense tracking for both Oikos’s own portfolio and its co-hosting clients. Brendan only spends about an hour each week reviewing financial reports, a massive improvement from the manual process before.

This streamlined workflow not only saves time but also ensures accuracy, giving Brendan peace of mind. Now, Brendan can quickly reference past payments when questions arise from cleaners or property owners. Instead of digging through bank statements or scattered invoices, he can simply pull up the Breezeway task report and payment record tied to that job.

Happier cleaners, stronger accountability

One of the biggest challenges Oikos faced before Breezeway was maintaining strong relationships with its cleaning team. Cleaners were frustrated by delayed or inconsistent payments, often sending multiple messages to confirm when they would be paid. Without a reliable invoicing or payment system, trust and accountability were harder to maintain.

Breezeway Payments transformed this dynamic. Cleaners now know they’ll be paid automatically once their tasks are completed, creating peace of mind for them and fewer interruptions for Brendan. As a result, payment-related complaints have decreased tenfold.

This process has also created stronger accountability for the work itself. Payments are tied to tasks, each with a required photo checklist to complete. This ensures that Oikos receives accurate, professional documentation for each property cleaning and allows Brendan to monitor quality more effectively. As a result, Breezeway not only streamlined payments but also elevated the professionalism and accountability of Oikos’s cleaning operations.

A scalable solution for a growing portfolio

As Oikos Property Management expanded to around 30 properties, the limitations of its old system became impossible to manage. Brendan explained that early on, when managing fewer than 10 properties, it was possible to “get away” with a less structured process. But, as the portfolio grew, manual payment tracking and scattered communications created too many inefficiencies.

With Breezeway, Oikos has built scalable systems that support its growth. The integration with Hospitable ensures tasks are automatically scheduled from reservation data, while Breezeway provides the operational and financial infrastructure to assign, track, and pay vendors at scale. Brendan emphasized the importance of this: “Whenever you cross about 10 properties, having something like Breezeway and using it systematically and becoming a power user is a game-changer for your work. Everything is tracked there.”