From a single-unit listing to a boutique hotel management company: See how Occupied LLC achieved 47% in direct bookings & 94% occupancy

In 2017, Michael Sjogren and his wife Krysten founded Occupied LLC, a national short-term rental management company. 

The two launched the company as a vehicle to build passive income and began by renting out their own single-unit property. Upon seeing the huge profit potential of the short-term rental market, they soon started managing other people’s properties. From there, Occupied LLC began to rapidly grow. 

Within 18 months, their dream to stop trading away family time for a paycheck became a reality. The whirlwind success of their property management company meant that they could leave their corporate jobs, and focus all their efforts on growing their new business on their own schedule.  

Headquartered in Boston, Massachusetts, Michael and Krysten currently manage a portfolio of 21 short-term rental properties across five states – Massachusetts, New Hampshire, North Carolina, Florida and Texas. 

Their business took another huge step in February 2020, when they partnered with local investors to purchase their first boutique hotel, The Cove at Rockport, on Boston’s north shore. Even amid COVID-19, the hotel has exceeded all of their expectations, reaching 94% occupancy within its first year of opening throughout the summer of 2020. 

The Challenge

Growing from a single-unit to a boutique hotel property management company came with its own set of challenges.

“We were getting to a point where we needed to connect different technologies together. We were running on too many different systems, and I came to the conclusion that I needed one main platform that could integrate everything together,” said Michael. 

The Solution

Michael and Krysten experimented with a different PMS platform for a while, but they weren’t getting the capabilities they required, especially when it came to channel distribution and diversification. The more the company grew, they found they could no longer manage their operations or communicate effectively.

Needing a robust software that could support their growing team of cleaning staff, provide integrations to keyless entry solutions and security for guests, support 24/7 communication needs, and offer channel optimization, the pair made the choice to move to Guesty in 2019.

“Guesty’s one-stop-shop seduced us,” said Michael, “The fact that Guesty was offering guest communication services is what ultimately sealed the deal. When we began working with Guesty, we were at a stage in our business where we were generating income, but could not yet hire additional staff. Guesty’s platform was able to supplement this. Their Guest Communication Services has a major advantage over competitors for property managers who are looking for scaling and expansion.”

The Results

Guesty’s Direct Booking Website Builder has played a huge role in The Cove’s success – 47% of reservations are currently generated via direct bookings. The Pre-Stay tools, including automated check-in forms and rental agreements, ensure smooth self check-in processes for their guests. 

In addition, the Marketplace of vetted and approved third-party solutions gives Michael and Krysten the ability to directly integrate with a variety of tech tools to enhance their offering and ease their daily tasks, from luggage storage and dynamic pricing to a smart concierge service. And, the two can easily assign, track and supervise their teams’ tasks in real-time from the Mobile App. 

Thanks to time saved by Guesty, Michael and Krysten have been able to focus on expansion. After purchasing The Cove in February 2020, the two are now in the process of teaming up with local investors to purchase a second hotel in the area. And Krysten has been able to take on much more of a design role, ultimately leading to her being featured in Wayfair for the beautiful renovations and furnishings she conducted of The Cove.

“With Guesty, our focus shifted towards the boutique hotel world and we are very excited about this!” said Michael. 

“If you want to scale rapidly and streamline your business, you need to consider a steady PMS. Not a lot of PMS systems in the market offer a complete end-to-end solution like Guesty does. They offer the largest choice of OTA integrations, a robust technological choice, and a service for handling your guest communication that will bridge your internal gaps,” he added,  “We are very happy that we chose Guesty.”