Remote
SaaS
jobscollider
About this role
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. 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.
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.
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
Selling Motion
Sales Cycle
Enterprise
6–18 month cycles, complex multi-stakeholder deals
Prospecting
Hybrid
Mix of inbound leads and outbound prospecting
Buyer Persona
C-Suite
Selling to executive decision-makers
Territory
Named Accounts
Pre-assigned list of target companies
Requirements at a Glance
Typical Day — Account Executive
Estimates based on role type and selling motion — actual may vary by company.
Role Signals
Green Flags
Location flexibility
SaaS — Interview Intel
Typical Sales Cycle
30–90 days (SMB) · 3–9 months (Mid-Market) · 6–18 months (Enterprise)
Common Buyer Objections
- "We're locked into a contract with [competitor]"
- "We built something in-house already"
- "We don't have budget until next quarter"
- "Our team won't adopt another tool"
Key Industry Metrics
Hot Topics to Reference
- • AI-native product disruption
- • PLG vs sales-led motion debate
- • Vertical SaaS consolidation
- • Usage-based pricing models
Use these insights to speak the buyer's language in interviews.
Tags
Walk me through your discovery process.
Template questionHow do you handle a prospect who goes silent mid-deal?
Template questionTell me about your largest closed deal and the sales cycle.
Template questionHow do you build business cases for stakeholders?
Template questionDescribe a deal you lost and what you learned.
Template questionThis Account Executive position at Hostaway involves managing the full sales cycle from prospecting through close.
SaaS sales roles typically involve consultative selling with longer deal cycles.
Remote positions in sales offer flexibility but require strong self-discipline and proactive communication with distributed teams.
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