What problem did Upstay solve with Enso Connect?

Upstay needed one platform to deliver consistent guest experience across 400 properties, two brands, five markets, and multiple currencies. Spreadsheets, scripts, and PMS custom fields could no longer hold the operation together.

Upstay's leadership came up through luxury hotels, where standardization is the operating model: same TV, same furniture, same service script across every room. The team carried that mindset into short-term rentals and built guest communication the way you'd staff a hotel concierge desk, manually, with skilled people, working off shared documents. Hospitality was something they knew how to do.

It worked until the portfolio crossed into territory hotels never have to cross. 400 properties spread across Ottawa, Toronto, Hamilton, Kitchener, and Orlando. Multiple currencies. Two distinct brands, Upstay for vacation rentals in Florida and Casa Hotels for the boutique urban play in Toronto, each speaking to a different guest in a different tone. Mixed-format properties from 15-bedroom Orlando mansions to one-bedroom Toronto suites, with a fleet of locks - from Yale and Schlage to manual padlocks. Information lived in spreadsheets, scripts, PMS and other different sources.

Why did Upstay choose Enso Connect over other guest experience platforms?

Enso Connect was the only platform on Upstay's 20-feature evaluation spreadsheet to check every box, including the decisive requirement: multi-currency upsell support.

Upstay is bootstrapped. No outside funding, no impulse purchases. "We have to see the hole big enough to fill it," Bonnie Li, COO of Upstay, says. They built a spreadsheet with five candidate tools across the top and 20 wishlist features down the side. Upsells. Door codes. PMS integration. Multi-currency. Branded guest app, etc.

Enso Connect was the only platform that checked every box on the list.

Onboarding and Support with Enso Connect

Upstay went live on Enso Connect in late 2024, layered on top of Guesty PMS with the native integration carrying reservation data and custom property fields through as variables. The full onboarding package gave the team the support runway they needed to customize for every market and property type. Today, the relationship runs through a shared Slack channel where the team pings the Enso side for new feature requests and customization questions and gets answers quickly.

How does Upstay maintain Airbnb Superhost status across 400 properties?

Upstay assigns 12 to 16 named Superhost co-hosts to property clusters in-field, with each Superhost customizing their own Enso Connect auto-messages, guidebooks, and Boarding Pass content. Enso Connect handles the automated layer underneath so Superhosts focus on the relationship work.

Before the pivot, Upstay ran guest communication the way most growing operators do: a central team of remote agents answering messages and solving problems across the entire portfolio. It scaled, but it was anonymous. Guests were talking to "Upstay support," not a person.

The 2025 reset assigned a named Superhost to every property cluster, the person visible on the Airbnb listing, in the Boarding Pass, in the welcome message. Each Superhost has their own bio, their own style, their own way of communicating. Some lean warm and chatty, some are crisp and efficient. The system Upstay needed had to flex around distinct personalities at any given time, not standardize them away.

"We're not trying to run a stay from corporate anymore," Bonnie says. "A super host can customize her Enso pages and her auto messages based on her personality, her communication style. We're learning that a tool that's customizable is what really helps." According to Bonnie, the change drove the highest growth in guest ratings on Airbnb among short-term rental operators last year, a number Upstay attributes to the relationship work Superhosts can now do because Enso handles the repetitive layer below them.

How does Upstay run two brands on one Enso Connect platform?

Upstay runs vacation rentals (Florida) and Casa Hotels boutique hotels (Toronto) on a single Enso Connect deployment with separate Boarding Pass branding, separate guidebooks, and separate language tones for each brand. Guest journeys can be customized per brand without rebuilding the workflow for each property type.

Upstay and Casa Hotels speak to different guests. Upstay's Florida portfolio is family vacation rentals: Disney itineraries, villas with private pools. Casa Hotels is boutique urban hospitality in Toronto neighborhoods, with a different tone, a different voice, and a different recommendation set in the guidebook.

Both brands run on the same Enso Connect instance with separate Boarding Pass branding and separate guidebook content. A family staying at an Orlando vacation rental gets a family-friendly Disney itinerary in the guidebook. A business traveler at Casa Hotels gets cafes with good Wi-Fi and the nearest gym. Same platform, two distinct guest experiences, no rebuild required.

How did Upstay reduce after-hours guest support calls?

Upstay built a video tutorial for every lock type in its portfolio (Yale, Schlage, manual deadbolts, non-Wi-Fi padlocks) and loaded them into Enso Connect. The first response to "I can't get in" is now automated: verify the code, watch the video, escalate only if needed.

The Upstay portfolio runs on a mixed fleet of locks, Yale, Schlage, manual deadbolts, non-Wi-Fi padlocks. Every lock type has its own quirks: a check-mark button after the code on one, a specific sequence on another, a number that has to be punched in just so.

So Upstay built a video for every single one. Now when a guest messages "I can't get in" at 11 PM, the first response from the Boarding Pass isn't a human at all. It's two prompts: Did you enter the right code? Watch the video. The two-question mechanic catches most issues before a Superhost ever sees them. The team's middle-of-the-night phone calls dropped accordingly.

How did Upstay generate $130K in guest upsell revenue with Enso Connect?

Upstay generated $130K in upsell revenue by pairing its Superhost operating model with Enso Connect's Boarding Pass offers and Stripe checkout. Upsells include pool heating, chef recommendations, in-suite massage, paid early check-in tiers, and local activities.

The reason Upstay made the Enso Six Figure Club isn't that they pitched upsells harder than anyone else. It's that the Superhost model made the pitch feel like a recommendation from a friend. A Superhost who's already built the relationship with the guest, "you're going to Disney, you mentioned the kids and a private pool," can ask, naturally, in the flow of the conversation, "Would you like pool heating? I can cut you a deal for the week."

Enso Connect provides the link, the menu, and the seamless payment. "It really helps when you're closing the guest," Bonnie says. "You can say, 'go to this link, select the option, pay right there.' Payment needs to be seamless. The process needs to be seamless." The guest experience runs end-to-end without a single manual handoff.

The Enso features doing the heaviest lifting

Multi-Brand Presentation

Boarding Pass

Two brands - Upstay and Casa Hotels - running with separate branding, language tones, and guidebook content on the same Enso instance. The self-serve hub gives every guest their lock code, Wi-Fi, instructions, upsells, and local recommendations in one place. No more "spreadsheet here, script there."

→ Guest Autonomy

Customizable Per Super Host

Workflow Engine

Each of the 12 to 16 super hosts customizes their own auto-message cadence, tone, and content. The same platform supports a chatty warm super host and a crisp efficient one without rebuilding the journey for either. Standardized service, individual voices.

→ Team Personalization

Six Figure Revenue Line

Upsells & Experiences

Pool heating, chef recommendations, in-suite massage, paid early check-in tiers, local activities - all priced and presented through the Boarding Pass with seamless Stripe checkout. The result: $130K in upsell revenue and Enso Six Figure Club membership.

→ Revenue Generation

Mixed-Fleet Lock Library

Smart Locks

Yale, Schlage, manual locks, non-Wi-Fi padlocks - every device type in the portfolio has a video tutorial loaded into Enso. The "did you enter the right code, then watch the video" mechanic catches most lock issues before they reach a super host.

→ Operational Efficiency

Family vs Business Context

Digital Guidebooks

One hundred-plus entries per market, segmented by guest type and brand. Disney itineraries for Orlando families. Cafes with good Wi-Fi for Toronto business travelers. The team treats the guidebook as the central knowledge base their PMS could never hold.

→ Local Expertise At Scale

Custom Fields As Variables

Guesty Integration

The Guesty native integration pulls reservation data and custom property fields straight through as variables in Enso flows. The team's revamping the setup now to push more of the configuration up into Guesty and let Enso reference it once - rather than maintaining the same logic in two places.

→ Single Source of Truth

What's next for Upstay and Enso Connect?

Upstay is expanding Casa Hotels across Toronto neighborhoods, deepening its Autohost integration for guest screening, and trialing additional EnsoAI Autopilot capabilities on a property-cluster basis.

Casa Hotels is expanding with more boutique sites planned across Toronto neighborhoods over the next year. On the Enso side, the team is deepening Autohost integration for guest screening in markets where issue guests cluster around specific OTAs, and trialing more of EnsoAI's Autopilot capabilities as their head of guest experience validates each new category.

The mental model hasn't changed. Bonnie says: “We still need that human touch when it comes to people interaction. Hospitality cannot be done by software alone. We've learned that the right way to use Enso is as the assistant, amplifying our super hosts, not replacing them."