About Stay:
StaywithStay.com is not your typical rental marketplace. While we began as a short-term rental platform, Stay is evolving into a complete rental ecosystem—serving travelers, renters, property managers, and owners with bold new offerings across subscription-based listings, mid-term/long term rental experiences, and crypto-powered payment infrastructure.
We’re building the future of flexible living. To accelerate our growth, we’re looking for a driven, curious, and high-energy Sales Manager to help fuel demand across our marketplace and connect more people with smarter ways to rent and earn.
The Opportunity:
As a Sales Manager, you’ll be on the front lines of our growth engine—generating and qualifying leads, engaging property managers and owners, and playing a critical role in scaling our supply side. You’ll help drive adoption of our platform by identifying new opportunities, building strong relationships, and turning cold outreach into closed deals. This is a great role for someone who’s motivated by mission, hungry to learn, and excited to make an impact at a fast-moving startup shaping the future of renting.
Job Description:
As a Sales Manager at Stay, you will play a crucial role in connecting with potential clients who manage or own short term vacation rental properties. Your primary responsibility will be to make cold calls to qualified businesses/property management companies in the United States and Canada educating them about our services, and most importantly leading sales/demo calls, closing deals and when prudent scheduling calls for our senior leadership team.
This is an excellent opportunity for individuals who are driven and passionate about sales to earn a very competitive income.
Key Responsibilities:
- Conduct outbound cold calls and field inbound leads to generate opportunities, identify potential clients, and close sales. The initial lists and areas to target will be provided, and you can use an auto dial program or tools of your choice.
- Educate prospects on how Stay can increase their bookings and help them avoid high fees from Airbnb, VRBO and other sites, and on why we stand out compared to the competition.
- Set up and manage automated follow-up sequences and workflows in HubSpot to ensure consistent outreach, lead nurturing, and strong conversion momentum.
- Use HubSpot CRM tools to track engagement data, optimize outreach cadences, and improve overall pipeline efficiency—scaling high-quality touch points across leads and accounts.
- Build and maintain strong customer relationships through effective communication and follow-up, especially for large property management deals.
- Own the full sales cycle
- Collaborate with the sales team and marketing to achieve monthly and quarterly targets.
Qualifications:
- Proven experience in inside sales or telemarketing is required
- Excellent communication and interpersonal skills
- Ability and desire to do full cycle, soup-to-nuts sales
- Strong negotiation, persuasion skills, and followup skills
- Self-motivated with a positive attitude
- Existing relationships and/or experience in travel or vacation rentals is a big plus but not required
Comp & Benefits:
- Competitive base with an aggressive performance-based commissions & bonuses
- Opportunities for career advancement within a growing company, including promotion within the sales team to close business and extended upside performance-based comp
How to Apply:
Two actions are required: 1) Apply on LinkedIn. 2) Send your resume and a quick note about why you're the right fit to hello@staywithstay.com.
