Why STR operations are the secret to a five-star guest experience – lessons from Breezeway

When it comes to short-term rentals, it’s easy to focus on reservations, pricing, and occupancy rates. But according to Jeremy Gall, Founder and CEO of Breezeway, the true differentiator in this industry isn’t the OTA algorithm – it’s your operations.

On a recent episode of the Host Planet Podcast, Jeremy shared how mastering the operational side of your business – think property details, proactive communication, and workflow automation – is the key to delivering a five-star guest experience at scale. Here’s a look at some of the most important lessons from the conversation.

Catch the full episode on our website, YouTube, Spotify, or Apple.

The guest experience is built on invisible details

“Guests only see what’s on the surface,” Jeremy explained, “but behind every five-star stay are hundreds of invisible details.” As your portfolio grows, the complexity of managing these details multiplies. But the solution isn’t to build a huge team. Instead, it’s about creating smart, scalable systems.

Jeremy outlined four pillars for operational excellence:

1. Document every property detail – from appliance models to quirks of the layout.

2. Proactive guest communication – set expectations and alleviate concerns before they arise.

3. Clear accountability for every team member – cleaners, maintenance, and service partners must know what “done right” means for your brand.

4. Standardise and lean into processes – especially for turnovers, preventative maintenance, and guest safety.

   
   

Automation alone is not the answer – it’s about balance

While automation and AI are becoming essential tools for STR operators, Jeremy was quick to stress that hospitality is, at its core, a human business. Technology should be used to empower service teams and hosts, not replace them. “Automation helps you streamline the back-end, so you can deliver more human interactions where they matter most,” he said.

Breezeway’s approach focuses on automating the repetitive tasks – like maintenance schedules and messaging workflows – so hosts and managers can invest their energy into meaningful guest touch points. This balance of automation and human touch is what Jeremy sees as the future of property technology in STR.

Proactive communication can make or break the guest experience

One of the biggest pitfalls in short-term rentals is the unpredictability guests feel before arrival. “That trepidation guests feel – ‘Will it look like the photos?’ ‘Will everything work?’ – is what holds the industry back,” Jeremy explained. The solution is proactive communication.

Jeremy suggests a three-message strategy to build trust and set expectations:

1. Pre-arrival message (1-2 days before stay): Outline key property details and what to expect.

2. Day-of-arrival message: Reinforce important check-in info and ensure they’re comfortable.

3. Post-check-in message: Check in to see if everything meets expectations and catch any small issues before they become negative reviews.

   
   

Text messaging, Jeremy pointed out, is the ideal medium – non-intrusive yet personal enough to make guests feel cared for.

“Hope is not a strategy”

A recurring theme in the conversation was that many hosts undervalue their operational work, hoping things will run smoothly without robust systems. Jeremy’s advice? “Hope isn’t a strategy. You need to document, automate, and standardise operations if you want predictable results.”

He also highlighted a major industry mistake: over-prioritising booking channels and pricing strategy while overlooking the on-the-ground work that drives guest satisfaction and reviews. Efficient operations, he stressed, are the foundation of a scalable, profitable STR business.

Raising standards will drive industry growth

Looking to the future, Jeremy believes that higher operational standards and professionalism across the industry will benefit everyone – from guests and owners to the wider community. This elevation will also reduce regulatory pressures by positioning STRs as a mature, reliable sector. “Better actors in the space will push the whole industry forward,” Jeremy concluded.

Key takeaways from Breezeway CEO to improve STR operations:

• Operational excellence is the backbone of a five-star guest experience. Focus on property details, proactive communication, and streamlined workflows.

• Automation should enhance human service, not replace it. Tech empowers teams to deliver better guest experiences.

• Proactive messaging is essential to alleviate guest anxiety, build trust, and ensure smoother stays.

• STR operators need to move beyond “hope” as a strategy – documented processes and smart systems are non-negotiable for success.

• Raising standards across the industry will drive growth, reduce regulation, and improve outcomes for guests, owners, and communities.