Enterprise Account Executive
At a glance
Mid-level Account Executive role at Wander. Austin · full-time · $200,000–$250,000 OTE.
growthroles summary, based on the employer's posting.
What you'll do
- Create and convert opportunities among large vacation rental property management companies
- Build connections with owners and leaders in operations, marketing, revenue management and technology
- Uncover each prospect’s systems, booking approach and buying process, then tailor product demos to their priorities
- Make the commercial case for direct revenue, website conversion, guest retention and marketing efficiency
- Move group evaluations through negotiation and contracting, coordinate technical checks, and keep forecasts and handoffs clear
What you bring
- A history of hitting or surpassing quota while selling enterprise software
- Background selling to professional vacation rental managers, ideally at Track, Streamline, Guesty or another PMS provider
- Experience steering complicated sales with several stakeholders and executive buyers
- Knowledge of vacation rental systems, including PMS platforms, booking engines and direct-booking approaches
Who this fits
This mid-level enterprise sales role suits someone with vacation rental industry knowledge and experience winning complex software deals. Austin is preferred, with other locations considered for the right candidate. The role includes representing WanderOS at industry events and customer meetings.
From the employer
About WanderOS
WanderOS helps vacation rental property managers grow their direct-booking business. Our platform brings together conversion-focused websites, automated guest marketing, SEO, and AI-powered distribution, connecting with the property management systems operators already use.
We help property managers build stronger brands, deepen guest relationships, and grow revenue beyond third-party booking channels.
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.
Why Wander
Help shape how leading vacation rental operators grow their direct-booking businesses. You'll sell a product built around a clear customer need, work closely with the teams building and delivering it, and have a meaningful voice in how we scale enterprise sales.
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