Guesty Winwinnkeeper Partnership

  • September 17, 2017

Rasheid Scarlett, Great Dwellings
Ivo Gospodinov, WinwInnKeeper 
London, UK · Member since September 2016Director & Property Manager



In July 2015 Ivo and Miro, of WinwInnKeeper, rented an entire property for their family and themselves in London. When they saw this was becoming a more permanent arrangement, they seeked the landlord’s permission to sublet the other rooms of the property on a short-term rental basis to working professionals. As a result, the brothers ended up with £300 of profit after bills and free accommodation. They were pleasantly surprised, and replicated this with an additional two properties.

Soon they decided to take on a third property, and turn this into a business. Following some endeavours and a lot of perseverance, the brothers started acquiring properties using the Airbnb management model – growing to 28 properties by September 2016. They focused on creating a win-win situation between guests, landlords and themselves as a premium property management company.

Resulting from the hard work and increasing number of properties, the WinwInnKeeper team was able to obtain a corporate office for the growing number of employees. The office is located on Commercial Street in Shoreditch, London where the majority of the staff works. They provide their guests with welcome staff and premium cleaners within Greater London.

Today, WinwInnKeeper has over 120 properties under their management services. Having such a large number of properties, allows the company to start leveraging towards new potential clients by showcasing the ever-increasing portfolio and scaling their business to the next level. The majority of WinwInnKeeper’s portfolio is based in London; nevertheless the organization is reaching other locations worldwide, leading to the acquirement of properties in the Dominican Republic, United States, France and Bulgaria.


Following the growth of the company, Ivo and Miro identified that there was a need to review the company portfolio and see where they are over-spending and where they can cut-back and save. This pushed them to build a plan of how WinwInnKeeper could save costs while continuing to hire more staff. They took the next step to organize how to proceed in terms of property management in the modern day short-term rental industry.  

Managing an array of listings and bookings from various channels, such as Airbnb and, creates organizational challenges. If not handled properly, these challenges can create a sense of confusion for staff working on different aspects of the management model. Due to the rapid increase in their portfolio it was becoming more difficult to manage aspects such as cleaning services and meet and greets during check-in time. Additionally, they wanted to analyze how their business was performing. Keeping track of each individual property on a separate basis is not methodical and very time consuming for such a simple activity.

As the company continued to grow, so did the demand for a complete booking management software to streamline bookings all in one place. This need was portrayed throughout all departments in the company, specifically the staff of operations. This team was having issues communicating with guests in a timely manner upon bookings, check-ins, and other similar events. With information being sent to various inboxes and accounts, it was getting too hectic to manage.

It became clear to WinwInnKeeper that it was necessary for the implementation of a property management software to improve not only the workload for creating a more manageable flow, but the guest experience as well. After searching for the best property management software available, they came across Guesty.


Immediately, they found that Guesty eliminates the problem of multiple inboxes and reduces the confusion of property management systems. However, that was just one aspect the software resolved. Using the property management software has allowed the operations team, customer service, welcome staff and other members of the company to stay in the loop by tracking all the important information from platforms like Airbnb,, Homeaway etc. Guesty creates the element of streamlining the booking and management process by having all rental accounts in one interactive platform.

The channel management aspect of Guesty is crucial for WinwInnKeeper’s operation team. Using this tool permits employees to have access to a single dashboard where they can control various aspects like viewing and editing the calendar. Additionally, changing fundamentals of the listing aspect such as pricing and availability of all the properties, is much simpler under one platform.

Members of the operations team have to be on call 24/7 all year round for any guest enquiries before or during their stay. Using Guesty’s automation tools permits employees to save valuable time. The automated message system aids staff in producing reviews, responding to booking enquiries immediately, alerting guests of payment collection and other tedious tasks. A member of the operations team stated that “Guesty has been genuinely adaptable in adjusting to my requirements, therefore it has made my efforts significantly worthwhile.”

Guesty has also provided WinwInnKeeper with a successful and safe payment-processor. Using this service allows staff to collect and receive payments impeccably through the secure payment processor where employees can create auto-payment schedules with just a few clicks. Likewise, anyone part of the team can log any extra transactions that need to be made, see account balances, and send payment invoices to guests. “This is one of our most important Guesty features. Now I don’t have to deal with the old fashioned and confusing billing system – that alone is an enormous upgrade in efficiency,” declared the customer service team manager.

Not only have many members of the staff benefited from the use of Guesty, the software also allows homeowners to stay in the loop regarding their properties. Homeowners are able to view certain aspects of the listing, such as occupancy rate and current upcoming reservations. One of the long-term homeowners who has experienced life with and without Guesty specifies “With Guesty’s proficiency within Airbnb’s platform, I have the ability to stay informed with what is going on with my properties without the need to get in contact or hassle any member of the WinwInnKeeper staff”.

Business results for WinwInnKeeper from utilising Guesty

Once becoming Guesty users and the Guesty solution was applied to the WinwInnKeeper team’s property management model, they were able to focus on strategy rather than just day-to-day management. In return, staff were more organized and the company was were able to manage and conduct activity more proficiently. The most impactful change has been the way in which they managed their accounting and billing. The payment processing feature allowed the account managers to analyze their success and see where they can improve. This would not have been possible without Guesty’s powerful analytics system. Since incorporating Guesty into their management model, WinwInnKeeper has been able to grow from 28 properties in September 2016 to 121 properties in August 2017, which is very impressive for one year. Furthermore in correlation to the increasing amount of properties, the revenue has substantially increased from £32,786 to £273,136 per month in only 11 months. Now WinwInnKeeper is focussing on growth and providing the best possible and most efficient service to homeowners and guests. With 1300 units to be acquired by Jan. 2020, they definitely view Guesty as a key partner in their journey.