Inside Sales Specialist - 100% Remote - North America

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.

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.

About the role

As an Inside Sales Specialist at Hostaway, you will be responsible for growing revenue from our existing customer base by selling add-on products and expansion opportunities. This is a mid-level, quota-carrying inside SaaS sales role focused on proactive outreach, customer demos, pipeline management, and closing commercial opportunities.

Your mission

• Sell add-on products to existing customers, including solutions such as Dynamic Pricing, Smart Locks, QuickBooks Online, and Insurance.

• Run high-volume outbound activity through calls, emails, and demos to generate and progress expansion pipeline.

• Manage the full sales cycle for add-on opportunities, from discovery and demo through objection handling, negotiation, and close.

• Partner with Customer Success Managers to identify customer growth opportunities and lead the commercial sales process.

• Maintain accurate pipeline and activity records in Salesforce, including next steps, close dates, forecasting, and follow-ups.

• Meet or exceed monthly and quarterly revenue targets by consistently creating and closing expansion opportunities.

• 2 years of SaaS sales experience, ideally in inside sales, account management, expansion sales, or customer growth.

• Proven experience in a quota-carrying closing role, with a track record of meeting or exceeding revenue targets.

• Experience selling to existing customers, including upsells, cross-sells, add-ons, or product expansions.

• Comfortable with high-volume outbound sales activity, including calls, emails, follow-ups, and product demos.

• Strong discovery, qualification, objection-handling, and closing skills.

Strong CRM discipline, ideally with Salesforce, for pipeline management, forecasting, and activity tracking.

This role may not be right if:

• You prefer relationship management over outbound selling.

• You do not enjoy making high volume calls.

• You have not owned an individual revenue quota.

• Your experience is mainly Customer Success without closing responsibility.

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.