Sales Development Representative — Global Market

Stayd

About the brand

Stayd is a collective of vacation-rental brands across the US Sunbelt and the Mountain West: Renjoy in Colorado Springs, Beachside on the Space Coast, Blue Gems in Orlando, Haven in the Smokies, Host2Coast on Hilton Head, Joseph Ellen on the North Florida coast, and more. We support more than 3,000 homes today and are building toward 15,000 by 2030. Local brands keep their name and neighborhood; the shared team behind them handles systems, data and back-office work so local teams can spend their day on guests and owners.

The role

You talk to homeowners who are deciding whether to hand us an asset worth several hundred thousand dollars. The work is outbound and consultative: research, cold outreach, discovery, and enough honesty about what we can and cannot do that the owners who sign stay signed. Volume matters — this is a role with a daily activity number — but so does what happens on the call.

Unreasonable hospitality

We hold ourselves to what Will Guidara calls unreasonable hospitality: doing the thing nobody asked for, that nobody would have missed, and that they will tell someone about. A guest mentions in a message that it is their daughter's birthday, and there is something waiting on the counter when they walk in. An owner asks a question on a Sunday and gets a real answer, from a person, before Monday. We do not measure this in a survey. We measure it in whether the person on the other end felt looked after by someone who was paying attention. Everyone here is expected to notice things, and everyone here is trusted to act on what they notice without asking permission first.

Where you sit

You sit in Growth and report into the operations lead for this market. This role is remote and open to people anywhere in the Americas. You work every day with the guest experience team, the field operations team and the coordinators who schedule them — this is not a role where you are handed a queue and left alone. Because Stayd runs shared systems across every brand, a process you improve here tends to end up running in six other markets, which is the closest thing we have to a promotion path.

What you'll own

• A daily outbound activity number you own and report against
• Discovery calls with homeowners, and an honest read on whether we are a fit
• Keeping the CRM true — a pipeline nobody trusts is worse than no pipeline
• Following up on the timeline you promised the owner, not the one that suits you
• Handing off signed owners to onboarding with everything they need
• Telling us what you are hearing in the market, especially when it is inconvenient

What you bring

• Outbound experience — cold calls, cold email or door knocking — where you carried a number
• The ability to hear "I manage it myself and keep 100%" without flinching
• Clear spoken and written English
• Comfort in a CRM and with a base-plus-commission structure
• Persistence that stays polite

How to apply

Apply here — it takes about four minutes on a phone. You will answer a handful of questions written to find out what you can actually do, upload a résumé, and record a short voice note so we can hear how you sound with a guest. There is no cover letter and there is no portal account to create.

Every single applicant hears back from us, including a no. If we are not moving forward we will tell you, and we will tell you why. If you need an accommodation to complete this application, email careers@stayd.co — asking never counts against you.

What to expect

This is a long-term team role on a strong, established global team, with structured onboarding and ongoing support.

By applying, you agree that Stayd may contact you about your application by email and WhatsApp. Reply STOP at any time to opt out.

By applying, you agree that Stayd may contact you about your application by email and WhatsApp. Reply STOP at any time to opt out.