Sales Development Representative - 100% remote - North America - March Hiring Class

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 Airbnb, 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 Property Management System 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.

We are now hiring for our March Class, this will close on March 13th 2026.

About the role

• Research and identify potential clients and key decision-makers within target 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, target-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.