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Sales Development Representative - 100% remote - North America

December 31, 2025

NOTE: This is a FULLY remote role, but the candidate must be within North America to collaborate with their team, peers, and internal customers. You do not have to be in the specific country or city shown in this listing, but please only apply if you are physically based within North America. Hostaway is a SaaS startup that is transforming the vacation rental industry. With innovative solutions and partnerships with giants like bolthires, VRBO, and Booking, we're taking on the competition and winning. Leveraging our customer-centric core values, we consistently deliver results that encourage growth, learning, and innovation for our team, our customers, and the industry. As a profitable and growing company, this role is necessitated by our continued growth. Profitable, high-growth, and the first short-term rental PMS unicorn . Join us at our most exciting stage yet! Learn more about our recent valuation and story here. Hostaway is seeking a highly motivated Sales Development Representative (SDR) to join our team and drive our growth in the North American market. We’re looking for driven, hungry, Sales professionals who are keen to make an impact with their work. About the role • Research and identify potential clients and key decision-makers within bolthires industries and accounts in the North American market. • Conduct outbound prospecting activities, including cold calling, email outreach, and social selling, to generate interest and qualify leads. • Engage with prospects to understand their business needs, challenges, and objectives, and effectively communicate the value proposition of our products/services. • Collaborate closely with the sales team to develop and execute strategic outreach campaigns and follow-up strategies to drive engagement and conversion. • Maintain accurate and up-to-date records of all prospect interactions and activities in the CRM system. • Work closely with marketing to provide feedback on lead quality and campaign effectiveness, and leverage marketing materials to support outreach efforts. • Meet and exceed monthly/quarterly targets for qualified meetings and pipeline generation. • Previous outbound sales experience in a B2B SaaS environment. • Proven track record of exceeding targets and delivering results in a fast-paced, bolthires-driven sales environment. • Strong prospecting and cold calling skills, with the ability to effectively engage and build rapport with prospects over the phone and via email. • Highly motivated self-starter with a proactive and entrepreneurial mindset. • Excellent organizational skills and attention to detail, with the ability to manage multiple tasks and priorities simultaneously. • Team player with strong interpersonal skills and the ability to collaborate effectively across departments. • Experience using CRM systems (e.g., Hubspot) and sales engagement tools (e.g., Outreach, SalesLoft) is a plus. • Fluent in English (written and verbal), with excellent communication skills. • A 2nd language would be advantageous What we offer • Competitive Compensation: We offer competitive pay based on market rates in the country of the applicant. • 100% Remote: Enjoy the freedom to work from anywhere within your country of residence—be it a co-working space, your home office, or even your dining room table. The choice is yours. Just don’t ask to work in our office (we don’t have one). • Equity: Every role in our company comes with valuable stock options in a fast-growing and profitable company. This ensures we all share in the company’s success. • Values-Driven Leadership: Our Core Values are not just words we’ve written to make us feel good. We leverage them daily when making strategic and tactical decisions. • Professional Growth: Our rapid growth offers unparalleled learning and development opportunities, along with a multitude of career advancement opportunities. • Annual Paid Leave: The specific amounts vary by country and are aligned with country and/or contract-specific norms. • Geographic Specific Benefits: As an international employer, we offer different country-specific benefits such as Health Insurance and Pensions in countries where these perks are customary. The specifics depend on the country of the applicant. • Dynamic Team Culture: As a global company with team members in over 40 countries, our diverse and international culture fuels our innovation and creativity, providing a key pillar to our success (and making it a lot of fun to work here). Thank you for your interest. If you apply for this role, you will receive an email from our Talent Acquisition team after your application has been reviewed alongside the qualifications for this role and the qualifications of others who have applied. Apply tot his job

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...