Run before or at the top of every demo. Goal: find which 2-3 pain points are live so you can tailor the demo and proposal around what actually matters to them.
1. Walk me through how you currently handle amenities — who does it, how often, and what breaks down?
Listening for: manual process, time drain, stockouts, wrong quantities, staff doing it themselves.
2. How many properties are you running right now, and are you planning to grow in the next 12 months?
Listening for: current scale, growth ambition — sets up scalability and onboarding urgency.
3. What does your turn day look like? Who's on it and what takes the most time?
Listening for: housekeeping labor cost, coordination pain, burnout — opens Time Savings and Team Morale angle.
4. How are you handling your owner relationships right now — is amenity quality part of what you pitch to new owners?
Listening for: owner retention angle, competitive differentiation — this is often a hidden pain.
5. Are you doing anything around branded guest experience or direct bookings?
Listening for: Custom Branding and Direct Bookings interest — if yes, Harris Vacations ($410K) is your case study.
6. What are you currently spending on amenities per property per month — even a rough number?
Listening for: their cost floor. This is required to build a proposal that lands. Without it the price objection is unwinnable. If they don't know, ask about their last supply order or what they're paying per kit.
7. What's driving the timing for you looking at this now?
Listening for: peak season pressure, growth event, new hire, something broke — sets up urgency in the close.
Before you demo, note which themes came up. Lead the demo with those use cases. Use the matching case study in your post-demo email.