
One of the biggest luxury short-term rentals in Chicago was running on instinct instead of insight — inquiries coming in from OTAs, direct channels, building partners, and returning guests, but no unified system to understand who was booking, why they were booking, or how fast the team was responding.
Operational excellence was there. Revenue intelligence wasn’t.


How Chloe Fueled Luxury Short-Term Rental Commercial Engine
The team couldn’t reliably answer simple operational questions:
Where do our highest-value reservations come from?
Which building rentals bring the biggest profit?
How many inquiries do we lose due to slow response on an individual level?
Why do guests return? Which guests leave reviews?
What drives revenue: OTA exposure, direct marketing, or partner communication?
So Chloe stepped in and designed a unified HubSpot architecture built specifically for Short-Term Luxury Rentals—one that understands the difference between B2C guests, B2B building owners, and Corporate clients. The entire journey became measurable for the first time: every inquiry, response time, booking made, every ticket raised during the stay, and every post-stay review stitched together into one clean system.
Then Chloe layered in intelligence. Realestate negotiations are tracked from the first outreach to the signed agreement. Repeat guests are recognized the moment they return. Reservation probability is no longer a guess but a measurable signal. And for the first time ever, revenue can be attributed to the exact source — whether it came from an OTA, an ad campaign, a referral partner.
When Chloe builds the system, your reservations finally have context, your team finally has clarity, and your entire commercial engine finally has control.
Give My Guests, Partners & Team One Shared Brain
Complete visibility from inquiry → reservation → stay → review → revenue
Saved weekly by automating intake forms, lead qualification, and renewal follow-ups through connected JotForm HubSpot workflows.
Contacts reactivated through segmented email nurture campaigns for B2B, B2C, and Family Entertainment audiences.
Industries fully automated — each with unique JotForms that route submissions instantly to the right pipeline in HubSpot.
Fields mapped per form, turning every submission into a structured PDF ready for carrier review and processing.
Your hospitality business can’t scale on OTA bookings alone — not without understanding the guest, the partner, and the entire journey.
I’m Done Guessing — Build Me a System That Knows
