The Revenue You’re Leaving Behind Is Hiding in Plain Sight
Most property managers don’t have a revenue problem.
They have a time problem.
You’re already getting bookings. You’re already answering messages. You’re already coordinating turns. And every additional “revenue idea” sounds like more work—another thing your team has to remember to offer, track, and fulfill.
That’s exactly why upsells often stall out.
Not because guests don’t want add-ons. They do.
But because manual upsells rely on someone noticing the moment, sending the right message, and following through—every time.
This guide is the simplest way to start.
Below are 10 basic upsell automation setups you can implement in Jurny quickly. They’re designed to be high-converting, low-chaos, and easy to manage at scale—so you can increase ancillary revenue and lift revenue per stay without adding headcount.
Why Manual Upsells Don’t Scale
Manual upsells usually fail for three reasons:
- Timing is inconsistent. The offer goes out too early, too late, or not at all.
- The right guests never see it. Everyone gets the same message, or nobody does.
- It adds operational load. Your team is already stretched, so upsells become optional.
The fix isn’t “more upsell ideas.”
It’s an upsell system: automated, contextual, and triggered by what guests actually need.
That’s where AI-powered upsells and upsell automation change the equation.
Instead of blasting offers, you set clear rules—timing, sentiment, availability, inventory—and Jurny helps you deliver triggered upsell offers at the moments guests are most likely to say yes.
10 Basic Upsell Setups to Start with Jurny
Each setup below includes a simple baseline configuration: timing + AI triggers + rules + inventory + channel + message starter. You can refine later, but you don’t need perfection to start generating revenue.
1) Early Check-In
Why it converts: Guests value flexibility and hate waiting around.
- Schedule: 2 days before check-in @ 9:00am
- AI triggers: “early,” “arrive early,” “landing early,” “check-in time”
- Rules: sentiment ≥ neutral
- Availability: calendar availability ON (prevents overselling)
- Pricing: fixed per stay
- Channel: Email
- Message: “Arriving early? Early check-in is available for {amount}. Quick checkout: {pay_link}”
2) Late Checkout
Why it converts: It buys comfort on departure day.
- Schedule: day before checkout @ 6:00pm
- AI triggers: “late checkout,” “flight later,” “checkout time”
- Rules: sentiment ≥ neutral
- Availability: calendar availability ON
- Pricing: fixed
- Channel: Email or SMS
- Message: “Want a later checkout tomorrow? Late checkout is {amount} → {pay_link}”
3) Extend Your Stay
Why it converts: It’s the cleanest “new revenue” you can earn—same guest, same unit.
- Schedule: during stay → day 2 @ 10:00am (or 48h before checkout)
- AI triggers: “extend,” “stay longer,” “another night”
- Rules: sentiment ≥ neutral
- Availability: calendar availability ON
- Pricing: per night (or fixed upgrade)
- Channel: Email
- Message: “If you’d like to extend, we can add an extra night if availability allows. {amount} → {pay_link}”
4) Reserved Parking
Why it converts: High intent and easy inventory tracking.
- Schedule: 2 days before check-in @ 6:00pm
- AI triggers: “parking,” “car,” “drive,” “garage”
- Rules: sentiment ≥ neutral (optional: party size ≥ 2)
- Inventory: stock-based spots + auto-restore ON at checkout
- Pricing: fixed per stay
- Channel: SMS/WhatsApp
- Message: “Driving in? Reserved parking is available for {amount} → {pay_link}”
5) Pet Fee or Pet Welcome Station
Why it converts: Prevents surprises and reduces mess issues.
- Schedule: reservation confirmed → send immediately
- AI triggers: “dog,” “pet,” “bringing our pup”
- Rules: only if has pets = true
- Inventory: unlimited (fee) or stock-based (kit)
- Pricing: fixed
- Channel: SMS/WhatsApp
- Message: “Bringing a pet? Add the pet option here: {amount} → {pay_link}”
6) House Reset (Light Mid-Stay Clean)
Why it converts: Convenience without the cost of a full clean.
- Schedule: during stay → midpoint @ 10:00am
- AI triggers: “trash,” “towels,” “extra cleaning,” “refresh”
- Rules: stay ≥ 4 nights
- Inventory: unlimited (service)
- Pricing: fixed
- Channel: Email or WhatsApp
- Message: “Want a quick House Reset during the stay (towels/trash/refresh)? {amount} → {pay_link}”
7) Extra Towels / Linen Refresh
Why it converts: Low price, high satisfaction, prevents complaints.
- Schedule: day of check-in @ 12:00pm
- AI triggers: “extra towels,” “more towels,” “linens,” “blanket”
- Rules: sentiment ≥ neutral
- Inventory: stock-based + auto-restore ON
- Pricing: fixed
- Channel: SMS/WhatsApp
- Message: “Need extra towels or a linen refresh during your stay? {amount} → {pay_link}”
8) Grocery Essentials Pre-Stock (“Fridge Done” Lite)
Why it converts: Solves late arrival and “everything is closed.”
- Schedule: 72h–5 days before check-in (depending on your ops)
- AI triggers: “late arrival,” “kids,” “grocery,” “breakfast,” “coffee”
- Rules: sentiment ≥ neutral
- Inventory: unlimited (service)
- Pricing: fixed bundle
- Channel: Email
- Message: “Want essentials stocked when you arrive (water/coffee/breakfast basics)? {amount} → {pay_link}”
9) Work-from-Home Add-On
Why it converts: Strong differentiator on longer stays; attracts higher-quality guests.
- Schedule: 4 days before check-in
- AI triggers: “work,” “Zoom,” “meeting,” “laptop,” “Wi-Fi”
- Rules: stay ≥ 4 nights
- Inventory: stock-based + auto-restore ON
- Pricing: per stay
- Channel: Email
- Message: “Working during the trip? We can set up a Work Kit (monitor/ergonomic chair). {amount} → {pay_link}”
10) Arrival Comfort Drop (Water + Snacks + Basics)
Why it converts: Simple, high conversion, low complexity.
- Schedule: day of check-in @ 12:00pm
- AI triggers: “flight delay,” “hungry,” “store closed,” “arrive late”
- Rules: sentiment ≥ neutral
- Inventory: stock-based consumables + auto-restore OFF + low-stock alerts
- Pricing: fixed
- Channel: SMS/WhatsApp
- Message: “Want an Arrival Comfort Drop waiting (water/snacks/toiletries basics)? {amount} → {pay_link}”
The Fastest Starter Pack (If You Only Do 3)
If you want the fastest path to results, start here:
- Early check-in / late checkout (pure demand)
- House reset (convenience + review protection)
- Parking or comfort drop (high intent, easy yes)
Once these are running smoothly, you can expand into experience kits, seasonal offers, and mid-stay surprises.
FAQ
What are AI-powered upsells?
AI-powered upsells use guest intent, timing, and rules (like sentiment and availability) to offer add-ons automatically when they’re most relevant.
What’s the difference between automated and contextual upsells?
Automated upsells can be scheduled. Contextual upsells trigger when the guest’s conversation or stay conditions indicate it makes sense.
Will this create more work for my team?
It shouldn’t. The point of upsell automation is to reduce manual follow-up while increasing ancillary revenue, especially when inventory and availability are enforced upfront.
Which channel converts best: email, SMS, or WhatsApp?
Email works well for visual, higher-priced offers. SMS/WhatsApp win for quick, low-friction “yes/no” decisions.
Ready to replace task-chasing with outcomes? Book a Demo.
