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Salary: USD 200,000 - 250,000 / annual
WanderOS is a platform that helps vacation rental property managers grow their direct-booking business through conversion-focused websites, automated guest marketing, SEO, and AI-powered distribution integrated with existing property management systems.
You will own the full enterprise sales cycle for vacation rental property management companies, from prospecting and discovery through product demonstrations, business-case development, negotiation, and close. You'll develop relationships with owners, executives, and leaders across operations, marketing, revenue management, and technology. Your responsibilities include:
• Building and closing a pipeline of enterprise vacation rental property management companies
• Conducting discovery to understand each prospect's business, existing systems, direct-booking strategy, and buying process
• Delivering tailored product demonstrations that connect WanderOS capabilities to customer priorities
• Building credible business cases around direct revenue growth, website conversion, guest retention, and marketing efficiency
• Navigating multi-stakeholder evaluations, commercial negotiations, and contracting
• Partnering with product and technical teams to address integration questions without overpromising
• Working closely with onboarding and customer success to ensure smooth handoff from signed agreement to launch
• Maintaining accurate pipeline records and forecasts, and helping refine the enterprise sales playbook
• Representing WanderOS at industry events and customer meetings
Success means winning enterprise customers that are strong fits, building a healthy predictable pipeline, delivering against revenue targets, establishing trusted relationships across the vacation rental industry, and turning individual deal lessons into a repeatable enterprise sales motion.
REQUIREMENTS:
• Proven record of meeting or exceeding quota in enterprise software sales
• Experience selling to professional vacation rental property managers, ideally at Track, Streamline, Guesty, or another leading PMS provider
• Experience managing complex sales cycles with multiple stakeholders and executive decision-makers
• Strong understanding of the vacation rental technology ecosystem, including PMS platforms, booking engines, distribution, and direct-booking strategies
• Ability to translate product capabilities into clear, commercially grounded customer stories
• Strong prospecting, discovery, presentation, negotiation, and closing skills
• Ownership mindset: ability to create opportunities, manage pipeline, and move deals forward without rigid playbook
• Sound judgment about what to promise, when to bring in specialists, and how to build lasting customer trust
