Sales Development Representative (SDR)
Location: Hybrid / Remote-first, one day per week in our Newburyport, MA office (Wednesdays)
Type: Full-time
About Stay
StaywithStay.com is not your typical rental marketplace. We're a short-term rental platform built to give property managers and owners a better deal; more bookings, direct guest relationships, and none of the punishing fees that come with Airbnb and VRBO. Travelers get a smarter way to book vacation rentals; owners and managers get a partner that's actually on their side.
We're scaling supply aggressively across the US and Canada, and we're looking for a driven, curious, high-energy SDR to fuel that growth.
The Role
You'll lead the top of our supply-side funnel. Your job is to reach property managers and owners, start real conversations, qualify the fit, and book qualified meetings for our Sales Leader. You are not closing deals. You are creating the pipeline that gets closed. If you want to close eventually, this is the on-ramp.
Target: >= 50 qualified meetings booked per month.
What You'll Do
- Run outbound cold calls and sequences to property managers and vacation rental owners across the US and Canada. Target lists and territories are provided.
- Work email and other comm sequences alongside calls; multi-channel, not phone-only.
- Educate prospects on how Stay drives more bookings and cuts the fees they're paying to Airbnb, VRBO, and other OTAs.
- Qualify prospects against clear criteria and book meetings for the Sales Leader.
- Follow up persistently and log everything in the CRM.
- Report on activity, conversion, and what's working; help us sharpen the pitch.
What You Bring
- 1+ years in outbound sales, SDR, BDR, or telemarketing; or a compelling reason you'll be great at this without it.
- Excellent phone presence and written communication.
- Comfort with rejection and the discipline to keep dialing.
- Self-motivated; you don't need someone watching your activity dashboard.
- Experience in Hubspot is a plus, not a requirement.
- Interest in travel, hospitality, or vacation rentals is a plus, not a requirement.
Comp & Benefits
- Competitive monthly pay, with performance-based commissions & bonuses
- Opportunities for career advancement within a growing company, including promotion within the sales team to close business and get a more aggressive performance-based package
How to Apply
Apply through LinkedIn. If you want to stand out, also email your resume and a short note on why you're a fit to hello@staywithstay.com.
