Short-Term Rental AI Automation & Direct Booking Growth Specialist (OwnerRez)

Project Overview I own and operate a portfolio of 10 short-term rentals generating approximately 285 bookings annually. As I prepare to scale, I am seeking an experienced automation and systems specialist to design and implement an AI-enabled operational infrastructure that reduces daily management workload while improving guest experience, listing performance, and long-term scalability. This engagement is focused on building a durable, low-maintenance system — not basic chatbot setup or one-off automations. Current Technology Stack PMS: OwnerRez Dynamic Pricing: PriceLabs Distribution: Airbnb, Vrbo, Booking.com, Google Vacation Rentals Direct booking website Primary Objectives Significantly reduce daily operational workload through intelligent automation Automate guest communication and operational workflows end-to-end Improve listing clarity, conversion efficiency, and guest self-service Implement AI-assisted listing optimization with owner approval controls Ensure OTA compliance while minimizing manual platform updates Build scalable infrastructure to support future portfolio growth Scope of Work 1. Guest Communication Automation AI-assisted inquiry responses & FAQ handling Booking confirmations & pre-arrival instructions Mid-stay check-ins & checkout messaging Review request workflows Escalation logic for complex or sensitive inquiries 2. Operational Workflow Automation Turnover & cleaner notifications Arrival/departure triggers & task workflows Smart lock code delivery processes Maintenance alerts & issue escalation 3. AI-Driven Listing Optimization System Competitive listing & review keyword analysis Generation of optimized titles & descriptions Amenity & feature positioning improvements OTA-specific formatting & compliance adjustments Change summaries requiring owner approval before publishing Designed to minimize manual edits and ongoing upkeep 4. Revenue & Performance Optimization Support Identify opportunities to reduce guest inquiries through listing clarity Provide approval-based pricing & stay rule recommendations (overlay to existing pricing software) 5. Review & Reputation Workflow Automated review request timing AI-assisted review response drafts Sentiment monitoring & trend insights 6. Reporting & Performance Visibility Response time & automation performance metrics Listing performance & guest communication insights Monthly summary of improvement opportunities System Requirements Approval-based workflows (no auto-publishing without review) OTA-compliant messaging & content formatting Scalable, modular architecture Reliable operation during peak occupancy periods Minimal ongoing manual intervention required Desired Outcomes Measurable reduction in daily messaging and coordination workload Improved guest experience through proactive communication Clearer listings resulting in fewer repetitive inquiries Durable systems designed for long-term scalability Owner time commitment reduced to minimal oversight Ideal Candidate Profile Proven experience with short-term rental or hospitality workflows Advanced automation & systems integration expertise Familiarity with PMS platforms (OwnerRez preferred) Experience implementing AI within operational workflows Systems thinker focused on reliability, efficiency, and scale Able to design solutions that remain stable under high booking volume Engagement Structure Initial phase will include a paid audit and architecture plan, followed by phased implementation. This role may evolve into an ongoing optimization partnership. ⚠️ Note to Applicants: Please include examples of complex automation systems you have designed and the operational impact achieved. Apply tot his job Apply To this Job