About WanderOS WanderOS helps vacation rental property managers grow their direct-booking business. Backed by GV and Redpoint.
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. Found on 1752vc Careers, the job board for startup and VC roles.
What they're looking for
- 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
More about this 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.
- 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...
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