Enterprise Account Exec — Vacation Rentals & Direct Booking

Wander; United States; Remote; USD 200,000 - 250,000; Full time

Job summary

Wander is seeking an Enterprise Account Executive who understands the vacation rental industry and can earn the trust of its largest operators. You’ll own the sales cycle from opening conversations through discovery, demos, and close, helping customers see how WanderOS fits their tech stack and growth goals.

The ideal candidate has sold enterprise software to vacation rental PMS providers, with established relationships and a track record of winning complex deals.

Qualifications

• 5+ years of enterprise software sales experience.
• Experience selling to vacation rental property managers (Track/Streamline/Guesty or leading PMS).
• Experience managing complex sales cycles with multiple stakeholders and executive decision-makers.
• Strong understanding of the vacation rental tech ecosystem (PMS, booking engines, distribution, and direct-booking).
• Ability to translate product capabilities into a clear, commercially grounded customer story.

Responsibilities

• Build and close a pipeline of enterprise vacation rental PMS customers.
• Lead discovery with owners, executives, and leaders across operations, marketing, revenue management, and technology.
• Deliver tailored WanderOS demos tied to the customer’s priorities.
• Develop credible business cases around direct revenue growth, website conversion, guest retention, and marketing efficiency.
• Navigate multi-stakeholder evaluations, negotiations, and contracting.
• Collaborate with product/tech teams to address integration questions and validate requirements.
• Coordinate with onboarding and customer success for a smooth handoff from contract to launch.
• Maintain accurate pipeline records and forecasts.
• Represent WanderOS at industry events and customer meetings.

Skills

Enterprise software sales

Quota achievement

Multistakeholder selling

PMS industry knowledge

Direct-booking strategy

Tools

PMS platforms

Booking engines

Direct-booking systems

Job description

Wander is seeking an Enterprise Account Executive who understands the vacation rental industry and can earn the trust of its largest operators. You’ll own the sales cycle from opening conversations through discovery, demos, and close, helping customers see how WanderOS fits their tech stack and growth goals.

The ideal candidate has sold enterprise software to vacation rental PMS providers, with established relationships and a track record of winning complex deals.