SkyShare Scales from 22 to 140 Properties with Hostaway

Fifteen years ago, Genevieve and her husband Tyler dipped their toes into the short-term rental market, listing their own properties for extra income. What started as a side hustle quickly turned into a profitable venture, leading them to expand their portfolio with properties acquired specifically for short-term rental. By 2020, they officially launched SkyShare Management, a full-service vacation rental management company, to meet the increasing demand from new clients.

Today, SkyShare Management has grown into a thriving business with more than 140 properties under management, a growing team and a reputation for delivering exceptional guest experiences. Their secret? A combination of proven listing strategies, hands-on property management and a commitment to guest service excellence. And with Hostaway powering their operations, they’ve been able to scale their business efficiently while maintaining top-tier service.

Company Bio: SkyShare Management

• Founded: 2020

• Headquarters: Nashville, Tennessee, USA

• Listings: 140 properties

• Employees: 6 full-time, 4 part-time

• Partners: Genevieve and Tyler Thompson

• Started with Hostaway: December 2021

How SkyShare Management Stands Out

1. Proven listing strategies

With over 15 years of experience, Genevieve, Tyler and their team have developed data-driven strategies that maximize occupancy and revenue on platforms like Airbnb, VRBO and Booking.com. By combining deep platform knowledge with dynamic pricing tools, SkyShare ensures homeowners earn the highest possible return on their investments.

2. Hands-on property management

SkyShare is committed to maintaining properties at the highest standards to ensure both guest satisfaction and cost-effective upkeep. They’ve built an extensive network of professional service providers for HVAC, electrical work, pest control and other maintenance needs, all at competitive prices.

3. Guest service excellence

Their success is built on delivering exceptional guest experiences. The SkyShare team takes a proactive approach to guest communications, ensuring every visitor has everything they need for a seamless stay. They provide 24/7 guest support, going above and beyond to deliver 5-star service.

“Five to seven years ago, a basic understanding of travel platforms was enough. Now, you need to be more hands-on to truly succeed.”

The Challenge: Scaling a Business Without a PMS

Before adopting Hostaway in December 2021, SkyShare Management was managing just 22 properties, most of which they owned. At the time, their operations were entirely manual, requiring them to handle every aspect of the business without automation. This included managing guest communication across multiple booking platforms, constantly adjusting pricing optimization, preparing owner reports and financial statements and coordinating maintenance and cleaning services. As their portfolio grew, these manual processes became increasingly time-consuming and inefficient, making it clear that they needed a more scalable solution.

“We were stretched thin, handling everything manually. We knew there had to be a better way.”

As they prepared to hire their first full-time employee, it became clear that manual operations weren’t sustainable. They needed a scalable solution to streamline processes, automate tasks and free up time for growth.

Finding the Right PMS: Why Hostaway?

Genevieve and Tyler conducted extensive research, evaluating multiple PMS options through online searches and demos. After comparing various software providers, Hostaway emerged as the clear choice for several key reasons. As an all-in-one solution, it seamlessly managed bookings, pricing, guest communications, financial reporting and maintenance coordination, consolidating all essential operations into a single platform. Its scalability made it an ideal fit for their rapidly growing portfolio, supporting their expansion from 22 to 140 properties. 

Additionally, Hostaway’s competitive pricing provided a cost-effective alternative compared to its competitors. Lastly, the strong customer support and smooth onboarding experience reassured Genevieve’s team that they were making the right decision, setting them up for long-term success.

“Hostaway had some ‘grit’—something we really aligned with on a personal level.”

Seamless Onboarding with Hostaway

Transitioning from no PMS to a fully automated system was a big step, but Hostaway’s support team, led by Andrew P., made it seamless.

“Going from no PMS to a full system is daunting, but Andrew walked us through everything and made it effortless.”

Within weeks, SkyShare Management was fully operational on Hostaway, optimizing their processes without disrupting existing business.

How SkyShare Uses Hostaway Today

Hostaway is now fully integrated into Sky Share Management’s daily operations, streamlining key processes and enhancing efficiency. Messaging automation centralizes all guest communications, enabling quick and seamless responses across multiple platforms. Dynamic pricing and calendar management allow the team to actively monitor and adjust pricing daily, ensuring maximum revenue optimization. Financial reporting has been simplified with clean, professional owner statements that make revenue tracking effortless. Additionally, damage deposit management has been streamlined, providing a secure and efficient way to handle security deposits while protecting property owners without adding complexity.

“Hostaway is the foundation of our business. There’s no way we could have scaled the way we have without it.”

The Results: SkyShare Management’s Growth with Hostaway

The numbers speak for themselves, showcasing SkyShare Management’s remarkable growth and efficiency. With an impressive 90% occupancy rate across all properties, they have consistently delivered strong returns for their clients. Their revenue growth has doubled for every client, with no instance where revenue hasn’t increased.

By automating operations with Hostaway, they have saved over 100 hours per month that were previously spent on manual tasks. Their portfolio has expanded from 22 to 140 listings, marking a 490% increase in just three years. Perhaps most notably, their client retention rate remains outstanding—90% of new clients come through word-of-mouth and not a single client has ever left.

Lessons Learned & Advice for Property Managers

Looking back, Genevieve & Tyler’s’s biggest regret is not adopting Hostaway sooner. Her advice to other short-term rental businesses is to invest in the right technology early rather than waiting until operations become overwhelming. 

She emphasizes the importance of thinking ahead and always preparing for the next phase of growth to avoid being caught off guard. Embracing automation is imperative, as manual processes can be time-consuming and ultimately hinder scalability. Lastly, she highlights the need to build a strong, reliable team that understands and effectively utilizes the systems in place, ensuring a smooth and successful expansion.

“It’s not always easy—scaling puts pressure on you to succeed—but with the right tools, it’s possible.”

The Future: What’s Next for SkyShare Management?

SkyShare Management is preparing for its biggest growth year yet. With their systems fully optimized, they are now set to expand into new territories, starting with their first Florida property already in their portfolio. Additionally, they are focused on forming more strategic partnerships, similar to their successful collaboration in Cape Cod, by working with partners who aspire to scale but lack the necessary infrastructure. As they continue refining their operations, their streamlined systems position them for even greater efficiency and long-term success.

“We’re finally at the point where we can scale efficiently and it’s all thanks to having the right systems in place.”

The Right PMS Makes All the Difference

SkyShare Management’s journey proves that the right technology is essential for scaling a short-term rental business. By adopting Hostaway, they streamlined their operations, saving valuable time, increasing revenue, enhancing guest satisfaction and scaling efficiently. Their success serves as a testament to the power of automation and strategic growth. For property managers looking to take their business to the next level, SkyShare Management’s experience with Hostaway demonstrates that the right tools can make all the difference.

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