Account Executive - 100% Remote - North America

Hostaway; Chicago (IL); On-site; USD 90,000 - 130,000; Full time

Benefits offered by this job

Remote work

Equity

Career growth opportunities

Annual Paid Leave

Country-specific benefits (health, etc

Job summary

Hostaway, a global AI-powered vacation rental platform, is seeking an Account Executive for a fully remote role within North America. You will drive growth in NA markets, owning the full sales cycle from lead to close and collaborating with marketing, product, and success teams.

You will build relationships with C-level stakeholders, craft strategic plans, and provide market insights to inform the company’s NA expansion.

Qualifications

• 3+ years of B2B SaaS sales experience as an Account Executive, managing the full sales cycle.
• Proven track record of exceeding quotas in a fast-growth environment.
• Excellent negotiation, communication, and relationship-building skills.

Responsibilities

• Develop and execute a strategic account plan to achieve revenue targets within North American markets.
• Build and maintain strong relationships with key stakeholders, including C-level executives and decision-makers.
• Own the full sales cycle, with proven experience in both inbound and outbound activities.
• Collaborate with marketing, product, and customer success teams to tailor solutions that resonate with clients.
• Provide insights on market trends, competitor activities, and customer feedback to shape our North American expansion.
• Maintain accurate and up-to-date records of all client interactions, opportunities, and activities in the CRM system.
• Represent Hostaway at industry events, conferences, and networking opportunities to build brand awareness and expand our client base.

Skills

Account Executive

B2B SaaS

Sales cycle management

Negotiation

Relationship-building

Tools

Salesforce

HubSpot

Job description

Job Description

NOTE: This is a FULLY remote role, but the candidate must be within North America EST or CST to collaborate with their team, peers, and internal customers. P lease 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.

As we continue our expansion into the NAM market in 2026, we’re looking for high-impact Account Executives to drive growth. With strong product-market fit and increasing demand, this role is critical to our success in the region. If you thrive in fast-paced environments and are passionate about building relationships, we want to hear from you.

About The Role

• Develop and execute a strategic account plan to achieve revenue targets within North American markets.
• Build and maintain strong relationships with key stakeholders, including C-level executives and decision-makers.
• Own the full sales cycle , with proven experience in both inbound and outbound activities.
• Collaborate with marketing, product, and customer success teams to tailor solutions that resonate with clients.
• Provide insights on market trends, competitor activities, and customer feedback to shape our North American expansion.
• Maintain accurate and up-to-date records of all client interactions, opportunities, and activities in the CRM system.
• Represent Hostaway at industry events, conferences, and networking opportunities to build brand awareness and expand our client base.

Job Requirements

• 3+ years of B2B SaaS sales experience as an Account Executive, managing the full sales cycle.
• You’re a results-driven, proactive individual with strong negotiation and problem-solving skills.
• Proven business acumen and the ability to manage the complete sales cycle from lead to close, ideally in a fast-paced, transactional sales environment.
• Proven track record of exceeding quotas in a fast-growth environment.
• Excellent negotiation, communication, and relationship-building skills.
• Ability to work autonomously and adapt in a dynamic, evolving market.
• Familiarity with CRM tools (Salesforce, HubSpot) and sales automation platforms.

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.