Enterprise AE - Direct Booking Growth for Vacation Rentals

Wander; Austin (TX); On-site; USD 200,000 - 250,000; Full time

Job summary

WanderOS is seeking an Enterprise Account Executive in Austin, TX (or flexible location) to lead the sales cycle for major vacation rental property management companies. You will articulate how WanderOS fits into existing tech stacks, drive discovery, and close complex deals, leveraging relationships with operators and executives to deliver direct-booking growth.

The ideal candidate has proven enterprise software sales success in the vacation rental space, with familiarity of Track, Streamline,

Qualifications

• Proven record of meeting or exceeding quota in enterprise software sales.
• Experience selling to professional vacation rental property managers, ideally Track/Streamline/Guesty.
• Experience managing complex sales cycles with multiple stakeholders and executive decision-makers.

Responsibilities

• 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.

Skills

Enterprise software sales

Account management

Negotiation

Discovery

Presentation

Pipeline management

Tools

CRM

Job description

WanderOS is seeking an Enterprise Account Executive in Austin, TX (or flexible location) to lead the sales cycle for major vacation rental property management companies. You will articulate how WanderOS fits into existing tech stacks, drive discovery, and close complex deals, leveraging relationships with operators and executives to deliver direct-booking growth.

The ideal candidate has proven enterprise software sales success in the vacation rental space, with familiarity of Track, Streamline,