How Cascadia Getaways Harnessed AI to Make New Acquisition Successful

The growth bottleneck nobody talks about

Property management companies hit a familiar ceiling. The portfolio grows, but the support team can't keep up. Hiring takes time, and by the time new staff are properly trained and productive, the next growth spurt is already demanding another round of recruiting.

Cascadia Getaways broke that cycle. When the company acquired its first property management business this year, leadership didn't worry about guest services capacity.

"We just bought our first company and integrated it this week," said Ryan, who leads revenue and guest services. "Just knowing we can add another company's worth of properties in and not needing to hire additional guest service staff feels pretty good."

The infrastructure that made it possible

Cascadia Getaways deployed Conduit in March. Within months, the company reached 60 percent automation  and 4.9 communication scores across across 100 properties.

The impact on staffing has been quickly visible.

"We don't have to hire more headcount to pick up the phones," Ryan said. Normally, a company would have to scale their support team significantly to cover busy periods, but not them, instead they even made the role evolved. They're now curating the data added to the knowledge base to ensure the AI has the right information, and also spend more time on high-value tasks like upselling calls before guests arrive.

AI handles routine inquiries like lockbox codes, parking rules, local recommendations, and standard troubleshooting. Humans step in for escalations and anything requiring genuine empathy.

Quality didn't suffer

Efficiency gains often trade against service quality. Cascadia Getaways's numbers show the opposite.

Before Conduit, communication scores fluctuated between 4.8 and 4.9. After deployment, the score locked at 4.9 and hasn't dipped. "We haven't gone below 4.9 in the communication score," Ryan said. Guest reviews cite responsive, knowledgeable support. The AI's ability to pull local recommendations, hiking trails, restaurants, packing lists, creates an impression of on-the-ground expertise. "They really think they're talking to somebody local," Ryan said. "Which is huge."

From reactive to proactive

The team now runs programs that most property managers can't staff because they're too reactive, constantly fielding incoming requests.

• Pre-arrival calls go out before every stay. Team members confirm 24/7 availability, capture travel details, and reinforce brand recognition. Guests who booked through Airbnb learn the management company's name, critical for direct booking conversion later.
• Post-stay calls happen after checkout but before review requests. The timing is intentional. "That post-stay call gives the guests the opportunity to vent a little bit if they have any issues that came up before the review ask comes out," Ryan explained. Team members also mention that booking direct saves 15 to 20 percent.
• Concierge calls arrive two weeks before check-in. The day team offers in-home chefs, massage therapists, and local experience coordination. A vacation rental becomes a hospitality experience.

The AI strategy advantage

Ryan frames automation as competitive positioning: "I haven't met another property manager who has an AI strategy."

Most operators react to AI, experimenting with tools, testing features, seeing what sticks. Cascadia Getaways built a philosophy around it.

"Our long-term mission is that if you're not boots on the property or interacting with a guest, you're AI," Ryan said.

The framing clarifies every decision. Should AI handle this task? Only if it doesn't require physical presence or human connection. Should we hire for this role? Only if the work can't be automated.

The result: resources concentrate on property managers and cleaners, the roles that define guest experience.

"I want to have the highest paid property managers in the market because then we corner the market on talent," Ryan said. "Finding the best cleaners and the best managers is real hard in these markets."

Team evolution

When AI arrived, leadership addressed the obvious fear directly.

"It started off very much like making sure they felt comfortable with the fact that AI wasn't going to take their job," Ryan said. "AI was there so they could work on higher-level projects, more fun things."

The promise held. Team members expanded into new domains. One night-shift employee manages SEO and Google Analytics, and organic traffic has grown. Another night-shift team member is learning revenue management. Day staff run concierge programs and proactive outreach.

"They're not just playing guest service agents," Ryan said. "They're getting involved with more segments of the business because of this automation."

Morale reflects the shift. "It gives them more confidence. They're working for a company that's on the winning side. It always feels good to be a winner."

Documentation as a forcing function

Conduit implementation required Cascadia Getaways to formalize processes. Like many property management companies, Cascadia Getaways had grown organically without developing extensive standard operating procedures. Knowledge about property-specific details, guest communication protocols, and troubleshooting steps lived exclusively in the team's collective experience.

The AI deployment forced documentation. Policies, procedures, and edge cases now live in a knowledge base that trains both the AI and new hires.

"Now we have a manual for running a segment of our business," Ryan said. The documentation supports Cascadia Getaways's longer-term goal: building operational playbooks for the entire company.

What growth looks like now

The integration framework is set. New acquisitions drop into an infrastructure built to absorb them, without proportional headcount increases, without service degradation, without the traditional scramble.

"It's really allowed us to grow with confidence," Ryan said.

The next frontier: expanding Conduit beyond guest communications. Ryan envisions a unified platform handling homeowner inquiries, vendor coordination, and cleaner communication.

"I would love to have Conduit just be the control panel for everyone externally that we need to communicate with."

Results:

• 60 percent automation rate
• 150 properties per support rep on shift
• 4.9 communication score (maintained post-deployment)
• Team members upskilled into SEO, revenue management, and concierge services

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