Your reviews don't lie. Neither does a missed hair in the shower, an empty soap dispenser, or a Keurig pod left behind by the last guest. Behind every five-star stay is a cleaning team working hard under tight timelines, unclear expectations, and back-to-back turnovers. So we handed the mic to the professionals who do the work.
In our April ELEVATE webinar, Breezeway's Koryn Okey sat down with Jonathan Wicks, Founder of Well & Good Professional Services, a vacation rental servicing company operating across 18 locations nationwide, and Logan Robison, Owner of Bonnie and a Broom, a cleaning company in Arkansas who also publishes Same Day Turn, a newsletter with more than 9,500 Airbnb cleaners. The conversation was honest, practical, and at times a little punchy. Here's what every property manager should take away.
When Jonathan Wicks talks about guest readiness, he means something specific. His team evaluates every property against three criteria before marking a job complete: serviced, stocked, and safe.
Safe means checking for broken furnishings, strange odors, and any obvious hazards. Stocked means the right number of towels, laundered linens, and all the guest essentials are in place. Serviced means every surface is cleaned and disinfected. All three are required every time, regardless of the season.
That last point matters. Jonathan pushes back on the idea that standards should flex during the busy season. "I think during busy season is when you have to rely on your processes even more." Peak season is exactly when your systems need to hold, not when you quietly lower the bar.
This one generated the most nods in the virtual room. If you want extras done, like custom staging, specific item placement, or a particular broom in a particular closet, you can absolutely ask for it. But you need to pay cleaners for it.
Jonathan put it plainly: "Our teams will literally walk on our hands if you pay us for it. We'll do whatever you want, but you gotta pay us for it."
Both Jonathan and Logan use a two-tier checklist system to manage this well. There's a standard checklist that covers every property, every turn, every time. Then there's a separate work order for customizations, each with a defined task and a corresponding cost.
Logan takes it a step further by allowing hosts he works with to request up to 10 additional actions at no charge. "We know that every property is unique," he said. "You can give us 10 extra things, for example, water this plant, or double-check this vase, and we'll do them. But the fastest way to burn out a cleaner is adding little stuff every single time and not acknowledging that it is pretty inconvenient."
If you're managing a high-revenue booking and you want white-glove treatment, create a VIP work order with a rate that reflects the ask. Telling your cleaner "this is a really important booking" without any additional compensation is not motivation, it's pressure.
This was one of the harder truths of the conversation, and Jonathan didn't soften it.
"Property managers underestimate how many corners they are actually asking the cleaners to cut in order to get the job done," he said. "You want to have a home with 10 beds turned with one single washing machine and dryer. You're asking folks to do rinse and spins and quick washes. If we were to do this the way you technically want it done, you'd realize that's not actually what you're asking. You're asking us to do a micro version of that."
This shows up most clearly in laundry, turnaround windows, and late checkout/early check-in situations. Logan was direct on the last one: "You can let the guests check in earlier, or you can have a clean house. Which would you want?" When you accept a late checkout or early check-in on a same-day turn without adjusting the timeline or adding resources, you're making a choice, and your cleaning team bears the consequences.
If early check-in revenue is part of your business model, Jonathan suggests sharing some of that income with the people who have to execute on it. "Wouldn't it be nice if there was a conversation about it, so we could send another team, or send more professionals?"
No clean is perfect. Logan tells his team this regularly. "There has never been a single perfect clean, and there will never be a single perfect clean. It is impossible to clean an entire house to perfection in four hours."
What separates strong manager-cleaner relationships from brittle ones is how you communicate when something gets missed. Logan's approach: lead with what went right, then name the specific issue, then move on. "I love how you staged the beds. I love how you restocked this. I did notice that this small thing was missed, could you please make a note next time? That way, you're not damaging the relationship. You're making sure they feel valued, but you're also helping them understand the concern."
He also invests in recognition: cleaner of the month awards, before-and-after photo wins, shoutouts in Slack. "As long as they feel loved and appreciated, you can give them feedback. If you're only ever giving negative feedback, they're not going to stay with you for very long."
Jonathan added a structural point worth underscoring: the decision you make with your guest, whether to issue a refund, offer a discount, or otherwise make it right, is a separate conversation from the one you have with your cleaning team. Don't conflate them. "Those are two separate relationships. You are there to serve the guests. You have a partnership with your operator." Pulling a cleaner's full pay because you chose to refund a guest's cleaning fee isn't accountability; it's a fast way to destroy trust and lose good people.
If your cleaning team isn't completing Breezeway work orders, there's a good chance the problem isn't buy-in, it's that your checklist is too long.
Jonathan described seeing Breezeway templates that asked cleaning professionals to turn on every TV in the property and log guests out of streaming services. "Your cleaners aren't doing that. And so they're not going to fill out the Breezeway [checklist]. And now you've lost your entire flow."
His advice: start by stripping your checklist back to what truly needs to happen on every single turn. Get that core list right, add it to Breezeway, and make completing the work order feel easy and natural. Customizations and inspection items can live in separate work orders on a different frequency, handled by a dedicated inspector rather than a cleaner in the middle of a tight turnover.
Well & Good has completed more than half a million services, all with a Breezeway task started and finished. It's possible, but only if the checklist reflects reality.
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Logan said it early and said it often: "Cleaners and managers/hosts are on the same team. We're both trying to provide a five-star guest experience."
That sounds obvious, but it's easy to lose sight of when something goes wrong. The managers who build the strongest, most durable cleaning partnerships are the ones who genuinely want their cleaners to succeed and make that felt, not just said.
"If there's a fundamental 'I want you to be successful' and both sides can say that, it matters," Jonathan said. "We have partners who know that Well & Good wants them to be successful. They actually care. They want us to thrive. They want us to be in business."
Logan's version of that: some of his favorite hosts buy his cleaners Christmas gifts. They understand that the cleaner is the person making the property a five-star property. "The staging is great, the guest communication is important. But the cleaning truly is the most important part of that stay."
Jonathan closed with advice that applies well beyond the manager-cleaner relationship: "Take a long game approach with your business. Take a long game approach with your partnerships. There are going to be bumps. There are also going to be a lot of great things. When we zoom out and say, we're crushing it, that happens with a long game approach."
The work behind a five-star stay is detailed, physical, and underappreciated. Cleaners aren't just checking boxes, they're touching every drawer, every cabinet, every surface, and walking out the door so the next guest feels like they're the only person who's ever been there. That takes time, standards, and trust.
The managers who understand that, who communicate clearly, compensate fairly, give feedback with kindness, and invest in their cleaning partnerships like they'd invest in any other long-term business relationship, are the ones building operations that hold up when volume is at its peak.
The rest are one busy season away from finding out the hard way.