Enhancing Guest Experience and Revenue with Happy Guest

Meet the Experts

Jamie Lane, Chief Economist at AirDNA, hosts the SDR Data Lab podcast, focusing on data-driven insights for short-term rental operators. Michael O'Connell, founder of Happy Guest, brings hands-on experience as both a property operator and a technology innovator in guest management systems.

O'Connell combines practical hosting experience with product development expertise. "We operate a small boutique property in South Florida, running guests through our place all the time. We're seeing firsthand what's going on and trying to solve the problems that smaller owner-operators face every day," he explains. His unique perspective comes from living the challenges he's now solving: "Everyone on our founding team has rented a room for a living and also worked on the tech side. That gives us a huge advantage—seeing the ins and outs, guest communication, where satisfaction lies, and what results in great reviews."

Together, Jamie and Michael explore how modern guest management solutions are revolutionizing the short-term rental industry in 2025.

The Evolution of Guest Management Systems in 2025

The Shift from Native Apps to Web-Based Guest Management

The guest management landscape has undergone a dramatic transformation in 2025. Gone are the days when hosts forced guests to download yet another app to their already cluttered phones. "In the early days of guest experience apps, they were all native apps—you had to download them. Now, in 2025, there are web apps you just click," O'Connell explains.

This shift removes friction from the guest experience. Modern web-based guest management systems offer superior functionality without the download barrier. "Your guest isn't downloading anything—it's a one-click link, their dates are in there, and they're ready to go," O'Connell emphasizes. This seamless approach has become the standard for the best visitor management system options in 2025, whether you're running a small bed and breakfast or managing multiple properties.

The evolution extends beyond mere convenience. Today's web apps perform better than their native predecessors, offering features like real-time updates, instant access to property information, and integrated communication tools—all without requiring storage space on guests' devices.

Addressing the Needs of Small Owner-Operators

The short-term rental industry in 2025 still has significant gaps, particularly for smaller operators. "There's definitely a lot of white space in the industry, and there still will be. I love seeing new companies pop up that solve some of these pain points, us being one of them," O'Connell observes.

Traditional enterprise-level guest management systems often priced out small operators with high onboarding fees and per-listing monthly costs. The new generation of platforms addresses this by introducing consumption-based pricing models. "Our pricing is different—we work on a consumption model. If you have upsells, we just take a percentage. There's no fee to come on board," O'Connell explains. This approach democratizes access to professional-grade tools, making the best visitor management system for small business operators finally affordable.

The philosophy is simple yet powerful: "We only make money if you're making money. That's the premise behind it." This alignment of interests ensures that platforms are invested in their users' success. Additionally, white-glove onboarding services have become standard, recognizing that small operators need support, not just software. "We hold your hand along the process: we integrate your PMS, and in five business days, you come back and everything's built out for you," O'Connell describes.

Improving the Guest Experience: Automation Meets Hospitality

Streamlining Check-In and Compliance

Modern guest management systems in 2025 have transformed the check-in process from a series of fragmented communications into a cohesive journey. "It's your one-stop shop for any information you need on checking in, signing your rental agreement, and once you're in the unit," O'Connell explains.

The integration of multimedia content has proven particularly effective. Property managers can now embed instructional videos directly into their digital guidebooks, addressing common guest questions before they arise. "A 15-second video on how to work a funky appliance or turn on a fire pit can be incredibly helpful," O'Connell notes. This proactive approach follows a simple principle: "A rule of thumb we've always implemented is: if two guests ask the same question, we're doing something wrong in our guidebook, and that's when we make a change."

Compliance automation has become another crucial feature, especially as regulations tighten across markets in 2025. Whether it's HOA forms, municipal requirements, or ID verification, modern systems handle these requirements seamlessly within the check-in flow. This automation is particularly valuable for properties in regulated markets, where manual compliance processes previously created friction and negative guest experiences.

Upselling and Ancillary Revenue in a Slowing Market

With ADR (Average Daily Rate) and occupancy trends showing pressure in 2025, maximizing revenue per guest has become critical. "A lot of operators aren't seeing the same numbers they had last year or the year before...getting smart and trying to pull the most revenue out of a guest is more important now than ever," O'Connell observes.

The opportunity is substantial, as evidenced by major platform investments. "Airbnb wouldn't release a full product line and spend $250 million on something they just came up with on a whim," O'Connell points out in regards to the introduction of Airbnb Services. However, technology alone isn't enough—proactive communication remains essential. "If you're not reaching out to the guest and making them aware that upsells or concierge services are available, you're probably going to miss out," he warns.

Successful operators in 2025 combine automated upsell opportunities with personal outreach. "One thing we do is call guests when they book and ask, 'Are you coming into town to celebrate anything?' It's a good leading question," O'Connell shares. This approach has led to creative revenue opportunities, from birthday decoration packages to early check-in and late checkout options. The results speak for themselves: "We had a guest who was booking multiple places and told Kanan he was coming for his girlfriend's birthday. We offered an upsell, decorated the place with balloons, and sent a video. Now we have a birthday upsell."

Balancing Automation and Personal Touch

The tension between efficiency and hospitality remains a central challenge in 2025. O'Connell offers a clear philosophy: "My philosophy is you should automate as much as possible to free up your time for hospitality." This approach recognizes that automation should enhance, not replace, the human element of hosting.

Successful operators in 2025 blend digital and physical touchpoints. While automated systems handle routine tasks, hosts invest saved time in creating memorable experiences. "I love mixing physical, tangible things with technology. Some people will never want to go through an app," O'Connell acknowledges. Examples include custom-printed seasonal newspapers featuring local events and discount coupons—tangible items that guests can take home as souvenirs.

This hybrid approach also accommodates different guest preferences. The data shows varied behavior patterns: some guests complete their entire check-in process immediately after booking, while others wait until the last minute. Modern systems must accommodate both, ensuring a smooth experience regardless of when guests engage with the platform.

Overcoming Common Challenges for Hosts in 2025

Flexible Cancellation and Lead Time Trends

The rise of flexible cancellation policies has fundamentally changed how hosts must approach bookings in 2025. "I've heard it described that with all these flexible cancellation policies, when you get a booking, it's essentially a qualified lead. Now it's on you as a host to make sure that guest actually stays at your place versus the others," Lane explains.

This shift requires a proactive strategy. O'Connell advocates for what he calls "flexing on your flexible cancellation"—using the initial booking as an opportunity to differentiate your property through personalized communication and exclusive offers. When guests book multiple properties with flexible cancellation, the host who engages most effectively wins the reservation.

Compounding this challenge, booking lead times continue to shrink dramatically in 2025. "Lead times are shortening heading into the summer. It's scary when looking at forward pacing. People aren't booking far in advance, but as you get closer to the stay, they book," Lane observes. This trend makes it even more critical for hosts to have systems that can quickly convert interest into confirmed stays.

Customer Support and Rapid Iteration

In the fast-paced environment of 2025, customer service quality and platform responsiveness have become key differentiators. "Your customer service has to be amazing in this industry, especially for anything guest-facing," O'Connell emphasizes.

Modern guest management platforms must adapt quickly to user feedback. O'Connell shares an example: when hosts reported confusion about time zones and daylight savings, his team fixed the issue in just 23 hours. "Our turnaround time on implementing changes is very fast. We take pride in that," he notes.

This commitment extends to testing and quality assurance. Rather than using customers as beta testers, responsible platforms test new features on their own properties first. "If something goes wrong, I can suffer from that review. We need to make sure we're giving you the perfect solution. That's big for me," O'Connell explains.

Measuring the Impact: Ratings, Loyalty, and Revenue

The tangible benefits of modern guest management systems in 2025 are becoming increasingly clear. Automated features like early check-in modules work seamlessly with cleaning schedules, creating new revenue opportunities without additional operational burden. "In Happy Guest, we have a module that automates early check-in, working with the cleaning or inspecting team. That system is completely automated," O'Connell describes.

The revenue impact is immediate for operators who haven't previously monetized these services. "For anyone not doing upsells, if you sell just one, you're net positive because we don't cost anything—we just take a 10% cut, but that's found money," O'Connell explains. Even simple strategies, like charging for late checkout, can generate significant additional revenue with minimal effort.

The efficiency gains are equally impressive. During the podcast, Lane received a guest request for early check-in, prompting O'Connell to note: "If you had Happy Guest, Jamie, they could have just purchased it and you could have made money while we were on this podcast." This real-time example illustrates how automation transforms time-consuming back-and-forth communications into instant revenue opportunities.

Beyond revenue, these systems impact guest satisfaction scores. "I suspect if we dug into the data, we'd see that hosts using Happy Guest have significantly higher check-in scores than others," O'Connell predicts. This improvement is particularly pronounced for properties with complex compliance requirements. "There isn't really a good rental agreement solution for small hosts. With DocuSign, you have to edit the dates yourself or let the guest enter them, which is a process in itself. There's friction if you're not using an STR-specific rental agreement solution," he explains.

The Future of Guest Management Systems: Community, Education, and Innovation

Looking ahead, the evolution of guest management systems in 2025 extends beyond software to community building and education. "We're doing a virtual conference called Revenue Rehab, focused on revenue management. We're holding these community-based events, open to anyone, where you can interact with other hosts," O'Connell announces.

This shift reflects a broader trend where technology providers become ecosystem partners rather than mere vendors. "Part of my job has become not just tech founder but support system. We have a big community of hosts now," O'Connell acknowledges. This community-centric approach helps operators navigate the rapidly changing landscape of short-term rentals.

The contrast with legacy systems becomes increasingly stark in 2025. "I see a lot of legacy systems based on what hosting was 10 or 20 years ago. Our tech is built off our experience as hosts and is there to make your life easier," O'Connell observes. This host-first development philosophy, combined with rapid iteration and community feedback, positions modern guest management systems as essential tools for success in the evolving short-term rental market.

As the industry continues to mature in 2025, the best visitor management system options will be those that combine cutting-edge technology with deep understanding of operator needs, seamless guest experiences with revenue optimization, and automation with authentic hospitality. For small operators looking to compete effectively, adopting these modern tools is becoming a necessity for survival and growth in an increasingly sophisticated marketplace.