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 Now
Apply Now
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 Now
Apply Now