Why Starting with StayFi from Day One Helped Cascadia Getaways Build a Direct Booking Machine (Customer Spotlight)

Overview

When co-founders Ryan Rabideau, Gerard Lester, and Stephanie Whitmore launched Cascadia Getaways, a boutique vacation rental brand based in Oregon, they weren’t just looking to manage properties. They set out to build a high-performing hospitality company fueled by technology, data, and strong operational systems. That mission began back in 2014, when an HOA approached Gerard about taking over management. From the very beginning, StayFi played a foundational role in what would become Cascadia Getaways.

Now managing over 75 properties across Oregon’s most desirable vacation markets, the company shows how starting with the right tools can set the stage for long-term growth. For them, StayFi wasn’t an add-on. It was part of the blueprint.

From Finance to Founding a Hospitality Brand

Ryan brought deep experience from leadership roles in finance and analytics at companies like Vacasa, Bungalow, Gather, and Rent Responsibly. Alongside co-founders Gerard Lester (Vacasa, Rented, Extenteam) and Stephanie Whitmore (Whitmore Properties, Gather Vacations), the team was well-positioned to scale smart. So when the opportunity arose, they approached it with rigor, purpose, and a scalable tech stack.

“I didn’t want to treat this like a hustle,” Ryan explains. “I wanted to build a real brand and you can’t do that without owning the guest relationship.”

Starting with StayFi: A Strategic Advantage

Unlike most operators who adopt StayFi later, Cascadia Getaways built it into their operations from the start. That meant every guest, from the very first booking, was added to their marketing database—even if they didn’t book direct. They also saved more than $18,000 in their first year thanks to StayFi’s ability to work with existing WiFi hardware, with a few helpful tweaks from the networking team.

“I didn’t want to lose a single guest email,” says Ryan. “From day one, StayFi has been part of our onboarding and operations. It’s just how we do business.”

That early move paid off. Cascadia Getaways captured over 6,000 guest emails in their first year and now consistently sees more than 40% of their traffic come through direct channels. Most managers never reach that level of direct engagement without years of investment in guest marketing tools.

The StayFi + Guesty Tech Stack

Key components of Cascadia Getaways’ stack include:

• StayFi: Captures guest emails through branded WiFi splash pages. Powers automated drip sequences and bi-weekly campaigns that educate guests on booking direct.
• Guesty: Their PMS of choice, offering the flexibility and scale needed to manage OTAs and streamline property operations.
• EZ Care: Handles all operations projects and collects guest feedback.
• RealTech: Their website partner, with features like exit-intent modals and “save my trip” email captures that feed into StayFi.
• Zapier + Meta: Guests who join the WiFi are automatically added to Facebook and Instagram remarketing campaigns.
• Conduit: AI-based guest communication, including personalized rebooking emails and texts.
• Studio82: Manages paid ad campaigns and uses pixel data to retarget guests who didn’t book.

A Smarter Approach to Direct Bookings

Cascadia Getaways focuses on efficiency, not vanity metrics. While many chase direct bookings for the sake of appearances, Ryan is laser-focused on profitable growth and guest lifetime value.

“I don’t want to outspend Airbnb on Google. I want to let them be the catcher’s mitt, then use StayFi to convert guests into loyal customers.”

StayFi powers:

• Collect guest emails through branded WiFi
• Run post-checkout drip emails, including follow-ups 10 months later
• Send bi-weekly updates about new listings and local events
• Build a strong brand presence through their website and direct campaigns
• Retarget WiFi joiners and site visitors who didn’t book

Why Starting Early Matters

Because Cascadia Getaways started with StayFi in place, they never had to play catch-up.

“Operators who wait miss out on thousands of guest contacts. For us, it was never an afterthought—it’s just how we operate. StayFi is part of our DNA.”

That early decision gave them a major advantage. With over 6,000 contacts in year one alone, they built a strong base of guest data that continues to power their growth today. For most operators, that kind of reach would take years to rebuild if they didn’t start early.

Lessons in Smart Growth

Over the last year, the company has:

• Migrated to a new PMS during peak season
  
• Rebuilt accounting systems
  

• Rolled out new AI tools for operations and guest messaging

• Refined internal SOPs to streamline workflows through automation

And they’ve done it all without sacrificing guest experience.

“Too many managers treat tech like an expense. StayFi is an investment—and it’s paid off in both brand equity and bookings.”