Stayd Collective

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Sales Development Representative

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 run more than 200 homes today and are building toward 400. Local brands keep their name and their neighbourhood; the shared team behind them handles the systems, the data and the back office so the local team can spend its 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, hired from Florida, Florida, United States. 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

How you'll live our core values

Five values run this company, and we hire and promote against them.

See Something Do Something - if you spot it, it is yours. Nobody here is allowed to walk past a problem because it belongs to another team.
Do What You Say - a commitment with a date on it is a promise. If it slips, you say so before it is late, not after.
Own the Miss - we get things wrong. What matters is that you name it first, fix it, and make sure it cannot happen the same way twice. Nobody is punished for a miss they owned.
Say the Hard Thing - kindly, directly and early. Silence in a meeting followed by a private complaint is the one behaviour we will not carry.
Make It Better - leave the process, the property or the shift in better shape than you found it. Small improvements, constantly, beat big ones occasionally.

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 resume, 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.

Benefits

Paid time off, paid US holidays, health insurance contribution, paid training, and a written path to a raise reviewed every six months. Equipment provided where the role needs it.