Outbound Sales Development Representative - 100% Remote - US

Hostaway; Chicago (IL); Remote; USD 55,000 - 80,000; Full time

Benefits offered by this job

Competitive pay

100% Remote

Equity

Career growth

Paid leave

Country-specific benefits

Job summary

Hostaway is seeking a highly motivated Sales Development Representative to join our team and drive growth in the North American market. This fully remote role requires you to be based in the US and to collaborate with a distributed team.

You will research target accounts, conduct outbound prospecting via phone, email, and social channels, qualify leads, and hand them to the sales team. A proven SaaS outbound track record is preferred.

Qualifications

• Outbound sales experience in a B2B SaaS environment.
• Proven track record of exceeding targets in a fast‑paced sales environment.
• Strong prospecting and cold calling skills with the ability to engage prospects via phone and email.
• Self‑starter with an entrepreneurial mindset.

Responsibilities

• Research and identify potential clients and decision‑makers in the North American market.
• Conduct outbound prospecting (cold calling, email, social selling) to generate and qualify leads.
• Engage with prospects to understand business needs and communicate value proposition.
• Collaborate with sales to develop outreach campaigns and follow‑up strategies.
• Maintain accurate records of prospect interactions in the CRM.
• Meet and exceed targets for qualified meetings and pipeline generation.

Skills

Outbound sales

B2B SaaS

Cold calling

Lead qualification

CRM

Team collaboration

Tools

CRM software

Job description

NOTE: This is a fully remote role, but the candidate must be within US, EST or CST to collaborate with their team, peers, and internal customers. Please only apply if you are physically based within Location/Timezone.

Trusted by 20,000+ property managers worldwide, Hostaway is an industry leading, AI-powered vacation rental management platform designed for professional short-term rental operators. Hostaway brings everything together for greater efficiency and faster 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 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.
• Meet and exceed monthly/quarterly targets for qualified meetings and pipeline generation.

Job Requirements

• 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.

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).