Enterprise Account Executive

About the role

We're looking for an Enterprise Account Executive who understands the vacation rental industry and knows how to earn the trust of its largest operators.

You'll own the sales cycle for enterprise property management companies, from opening the conversation through discovery, product demonstrations, business-case development, negotiation, and close. You'll help operators understand how WanderOS fits into their existing technology stack and supports their direct-booking and growth goals.

Our ideal candidate has sold enterprise software at a leading vacation rental PMS company, particularly Track, Streamline, or Guesty, and brings deep industry knowledge, established relationships, and a track record of winning complex deals.

Location: Austin, TX preferred; open to other locations for the right candidate. Compensation: $200k-$250k OTE.

What you'll do

• Build and close a pipeline of enterprise vacation rental property management companies.
• Develop relationships with owners, executives, and leaders across operations, marketing, revenue management, and technology.
• Lead discovery to understand each prospect's business, existing systems, direct-booking strategy, and buying process.
• Deliver tailored product demonstrations that connect WanderOS capabilities to the customer's priorities.
• Build credible business cases around direct revenue growth, website conversion, guest retention, and marketing efficiency.
• Navigate multi-stakeholder evaluations, commercial negotiations, and contracting.
• Partner with product and technical teams to address integration questions and validate requirements without overpromising capabilities.
• Work closely with onboarding and customer success to ensure a clear handoff from signed agreement to launch.
• Maintain accurate pipeline records and forecasts, and help sharpen our enterprise sales playbook.
• Represent WanderOS at relevant industry events and customer meetings.

What you bring

• A 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.
• A strong understanding of the vacation rental technology ecosystem, including PMS platforms, booking engines, distribution, and direct-booking strategies.
• The ability to translate product capabilities into a clear, commercially grounded customer story.
• Strong prospecting, discovery, presentation, negotiation, and closing skills.
• An ownership mindset: you can create opportunities, manage your pipeline, and move deals forward without a rigid playbook.
• Sound judgment about what to promise, when to bring in specialists, and how to build lasting customer trust.

What success looks like

• Winning enterprise customers that are a strong fit for WanderOS.
• Building a healthy, predictable pipeline and delivering against agreed revenue targets.
• Establishing trusted relationships across the vacation rental industry.
• Setting customers up for a successful launch through thoughtful discovery and clear expectations.
• Turning lessons from individual deals into a repeatable enterprise sales motion.