Trailblazers: Women Shaping the Future of Tech in Short-Term Rentals

In recent years, the landscape of the short-term rental industry has undergone a significant transformation. What was once a male-dominated field has evolved, welcoming diverse female professionals driving change with their unique perspectives and fresh ideas. This broader range of voices and talents promises to create a more dynamic and forward-thinking industry with women making their mark as innovators, leaders, and trailblazers in short-term property management.

The History of Women in Prop Tech

The roles women historically held in the short-term rental industry have changed dramatically. Today, women are forging different and exciting new paths to success, leveraging past experiences to excel in their current roles.

“I stumbled upon the industry, says Becca Madigan, Manager, Solutions Consultants, US at PriceLabs. “I found a position at a local vacation rental company and thought working at the beach sounded nice. Little did I know that this was a huge opportunity and the first step in my career.”

Madigan moved up the ranks quickly from Guest Services to Assistant Property Manager to Property Manager, ultimately earning a position as Director. “I learned more than ever about HVAC maintenance, plumbing, and interior design. I also learned about real estate and contract law, which still helps me today. Whether it was answering phones, prepping homes before owner arrivals, setting up the back end of a new PMS, or analyzing performance and developing new rate strategies— I loved how dynamic each role was and truly appreciate everything I learned during that time,” says Madigan.

Margot Schmorak, Co-Founder/CEO of Hostfully, started in the short-term rental industry in 2015. “In previous jobs, I was in Marketing (Worldwide Developer Relations at Apple and VP of Marketing at ServiceSource), Product and Operations (Head of both functions at Coveroo), and also in Sales (Head of Sales Strategy at ServiceSource). As a Co-Founder of Hostfully, my job has spanned across all functions,” says Schmorak.

Mary Beth Miles, CEO of Vacation Rental Collective, joined two co-founders as their first employee and Chief Operating Officer (COO) in 2017.  “It’s been quite the adventure! In 2017, we were a small team managing about 90 properties across four locations. Fast forward to today, and we’ve seen some remarkable growth. Our portfolio now boasts over 750 homes across 18 unique destinations. My career path has paralleled the company’s expansion. In late 2022, I stepped into the company’s CEO role with the strength and support of a fantastic team, “ says Miles.

The Current Prop Tech Landscape

With the integration of automation and other technological advancements, the property management landscape has undergone significant changes. Automated guest communication tools have streamlined reservation processes, while smart home devices offer even more convenience and control. More changes are on the horizon, redefining how short-term property managers operate and offering new levels of efficiency and personalization.

“​​This industry has exploded before our eyes. When we started Hostfully, only 17% of people in the U.S. had heard of Airbnb, and short-term rentals were envisioned only as summer vacation homes with antiquated booking systems that were often offline. Today, travelers expect to book a short-term rental online just like a hotel—with all the amenities, services, and loyalty programs that come with it. At the same time, the need for technology to provide this level of service to guests and owners has become increasingly urgent,” says Schmorak.

Adds Miles, “The landscape has been incredibly dynamic, with shifting traveler preferences, industry consolidation, and advancements in property tech and dynamic pricing. We’ve experienced both pandemic lows and highs, followed by significant market corrections. To adapt, we’ve prioritized agility, enabling us to respond to these industry shifts. We partnered with companies like BeHome247 to enhance our product offering, increase visibility into our homes, and improve safety and security for our homeowners and guests. And we’ve leaned into our commitment to hospitality, directing our team’s focus on delivering exceptional guest experiences through local expertise and personalized service. It’s been a journey of adaptation and growth, and we’re excited to continue navigating this evolving landscape.” 

Challenges and Opportunities

Limited access to funding, mentorship, and representation in leadership roles have presented challenges for women. They’ve also provided opportunities to drive innovation and reshape the short-term property management culture. 

“Outside of our market, there is still a lack of understanding of how big our market is and how fast it is evolving and growing. This can be frustrating because the industry isn’t given the level of credibility it deserves. But in some way, that’s ok because if you’re the underdog, you’re always beating expectations. As a female CEO and Co-founder, I wish there were even more women leaders in our industry. I think it is great for all of us,  including me, to see, hear, and feel different positive examples of how to lead. Every female voice helps to fill in a big void that has existed for a long time, and it’s time that we make this change as a broader community,” says Schmorak.

Another challenge is navigating the complex regulatory landscape, which has outpaced the development of regulations to govern it. 

“Operating across multiple markets means keeping abreast of ever-changing policies at the local and state levels, which can be quite demanding. We see this challenge as an opportunity to engage with local policymakers and our local communities. By actively participating in the dialogue and educating both elected officials and our neighbors about the positive impact of short-term rentals, we can foster a better understanding of our industry’s value. There’s immense potential for advocacy and positive public relations initiatives to highlight short-term rentals’ benefits to local communities. It’s about turning obstacles into opportunities for constructive engagement and mutual understanding,” adds Miles.

As these challenges affect operators and vendors, companies are stepping up with new offerings to help newcomers in the market handle the complexities.

“On the vendor side, I’m seeing operators struggle with an influx of new hosts in their markets. People who are not industry professionals are now doing what the professionals have done for many years and, in some cases, disrupting established markets. While I mainly work with larger customers at PriceLabs, our tools can be used by anyone from single-listing hosts to professionals with thousands of listings. One of our missions is to make data more accessible for everyone, so hopefully, we’re helping professionalize the new hosts in these markets. On the other hand, we are helping managers adapt to the changes in their markets,” says Madigan.

Future Short-Term Property Management Trends

The influx of newcomers in the market is expanding its reach, setting new standards, and elevating the industry to unprecedented heights.

What excites me most about the industry’s trajectory is the increasing professionalism among hosts. As more individuals and companies enter this space, there’s a noticeable elevation in standards and the overall guest experience. This evolution is not only raising the bar, but also shaping guest expectations, promising a future where short-term rentals continue to thrive and innovate,” adds Miles.

Moving forward, changing markets, evolving guest expectations, and technological advancements will significantly influence the industry, making top-tier property management services even more challenging. With their diverse perspectives and skill sets, women will no doubt continue to drive innovation and help shape the future. 

“I believe we are still in the early stages of innovation in the short-term rental industry, and we’ll continue to see rapid innovation for a while,” says Schmorak, who’s also excited to see new industry leaders bring different perspectives. “We can encourage this by being good listeners as the industry continues to change – to each other, to newcomers, and to the travelers who are also helping to transform our industry. I’m excited to hear more women’s voices at the table in this conversation,” says Schmorak.

It’s an exciting time for short-term rentals with women at the forefront, driving positive change and shaping the future of short-term property management. Their contributions are revolutionizing how properties are managed and setting new standards for excellence and inclusivity. As the industry continues to evolve, their leadership and innovative spirit will undoubtedly propel it forward, opening up new possibilities and redefining the guest experience.

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