← Guesty
Guesty role-play cheat sheet
For the mock cold call at the end of most SDR interviews.
What they sell, in one line
AI-powered software that helps short-term rental operators manage listings, bookings, guest messages, and operations in one place.
Who you'd be calling
Short-term rental hosts, property managers, and vacation rental company owners, from single hosts to large portfolios.
Your opener
“Hi [Name], this is [You] from Guesty. I know I'm interrupting your day, so do you have 30 seconds? I work with short-term rental managers, and I wanted to ask how much of your week goes to messages and scheduling.”
Problems you solve for them
- Managing many listings across booking sites by hand is slow and error-prone
- Guest messages and cleaning schedules take up the whole day
- Growing the portfolio without hiring more people is hard
Discovery questions to ask
- How many rentals do you run, and what tools do you use to manage them?
- Which tasks take the most time each week: messaging, calendars, cleaning, or payments?
- Are you planning to add more properties this year, and what would stop you?
Objections they'll throw at you
“I'm busy right now.”
→ Of course, I'll be brief. Can we set a quick 10-minute call for later this week when things are calmer?
“We're not interested.”
→ That's okay. Can I ask what you use today? If it's working well I'll leave you alone.
“We already use Hostaway or something else.”
→ Good tools exist out there. What do you wish yours did better, like automation, reporting, or support? That tells me if we're even worth a look.
“Just send me an email.”
→ Happy to. Tell me how many properties you manage so I can send something relevant. Is this the right email?
Competitors worth knowing
Hostaway, Hospitable, Lodgify, OwnerRez
Interview tips for this company
- Learn who the buyer is: it ranges from a solo host to a big operator, so ask early how many properties they have.
- Be ready to say what 'AI-powered' means in plain terms, like automated guest replies. Don't just repeat the buzzword.
Written from public information about Guesty to help you practice. Ask an insider what their role play looked like; it's the best prep there is.