Enterprise Account Executive

About Wander

Wander is revolutionizing the $100 B short‑term rental industry. We curate every aspect of the guest experience—from our smart homes to our intuitive booking platform. Our mission is to help people find their happy place, and our vision is to create the infrastructure for people to experience the world.

Backed by top‑tier investors and led by experienced startup veterans, we're a tight‑knit, remote‑first team united by our passion for travel, technology, and creating unforgettable experiences.

Location: Wander's Austin office on South Congress

About WanderOS

WanderOS is the operating system for direct bookings. We help vacation rental property managers compete with the OTAs with a conversion-optimized booking site, best-in-class SEO for Google and ChatGPT, automated lifecycle marketing, and AI-powered distribution. Today we power 600 property managers, 5,000 properties, and have facilitated $70M in direct bookings.

We're hiring an Enterprise AE to own our largest opportunities: property managers with 200 units, multi-brand portfolios, and category-defining boutique operators looking to take meaningful share back from Airbnb and Vrbo.

What you'll do

• Own the full sales cycle for Enterprise accounts (200 units), from first conversation to signed contract and successful handoff to onboarding.
• Build and execute a territory plan against a named account list of the top property management companies in North America.
• Run multi-threaded deals across founders, CMOs, Directors of Revenue, and Heads of Distribution. Most deals involve 4 stakeholders and a 60 day cycle.
• Lead consultative discovery focused on direct booking economics, OTA dependency, brand strategy, and PMS workflows. Translate findings into a tailored business case and ROI model.
• Run high-quality demos of the WanderOS site builder, booking flow, marketing automation, and PMS integrations. Bring solutions engineering in for technical deep dives.
• Negotiate pricing, commercial terms, and migration plans with VP and C-level buyers.
• Partner with Marketing on ABM plays, with Product on roadmap feedback from enterprise buyers, and with CS on a clean handoff that protects retention.
• Forecast accurately in HubSpot. Keep your pipeline, next steps, and MEDDPICC current.
• Represent WanderOS at industry events (VRMA, DARM, Book Direct, Streamline, Track Pulse).
  
  

What you'll bring

• 5 years of closing experience in B2B SaaS, with at least 2 years selling into Enterprise. Bonus for selling into vacation rental, hospitality, travel-tech, or e-commerce.
• A track record of consistently hitting $1M ARR quotas and closing six-figure ACV deals.
• Strong command of a structured sales methodology (MEDDPICC, Command of the Message, Challenger, or similar).
• Comfort selling a platform, not a point solution: you can sequence a multi-product story, defend price, and unseat incumbents.
• Sharp written and verbal communication. You can run a room of operators and a room of executives.
• Bias for ownership: you build your own pipeline, you don't wait for marketing to feed you, and you treat your territory like a business.
• Curiosity about how property managers actually run their business, what their guests want, and where the OTA model breaks down.
  
  

Nice to have

• Existing relationships in the vacation rental property management ecosystem.
• Experience selling alongside or against Boostly, Direct, Hostfully, Track, Streamline, Guesty, Hostaway, or similar.
• Familiarity with SEO, paid media, CRM, or email/SMS automation.
  
  

Why WanderOS

• A category that's actively rebundling. Property managers are done overpaying OTAs, and we're the platform helping them win.
• Real product velocity. We ship weekly and our customers feel it.
• Strong inbound from a brand (Wander) that operators already trust.
• Competitive base uncapped commission, accelerators over quota, equity, full benefits, and Wander stay credits.