Location: Wander's Austin office on South Congress
About WanderOSWanderOS 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.
