Job Summary

We are looking for a highly skilled and systems-oriented Lodgify Automation & AI Vacation Rental Specialist to design, configure, optimize, and maintain the technology and workflows that power our short-term rental operations.

This role goes beyond day-to-day property management. The primary focus will be on building and improving automated workflows across the entire guest journey—from inquiry and quoting through booking, payment, pre-arrival communication, check-in, stay, checkout, and post-stay follow-up.

The ideal candidate will have strong hands-on experience with Lodgify, vacation rental technology, workflow automation, AI tools, API integrations, and third-party partner platforms. They should understand how different systems communicate with each other and be able to identify opportunities to eliminate repetitive manual processes through automation and AI.

The candidate will also support the use of AI in website development, content, guest communication, workflow design, and operational processes, helping the business leverage AI to create a more seamless, scalable, and efficient operation.

Schedule: 9 AM to 6 PM EST, Riverhead, NY, with 1-hour unpaid lunch (8 hours/day, 40 hours/week)

Key Responsibilities

Lodgify Configuration & Optimization

• Serve as the primary systems expert for the Lodgify platform.
• Configure and optimize Lodgify settings, workflows, booking rules, automations, messaging, templates, rates, properties, and operational processes.
• Review the existing Lodgify setup and identify gaps, inefficiencies, and opportunities for automation.
• Build and modify Lodgify workflows based on business requirements.
• Configure Lodgify to support efficient quoting, booking, payment, guest communication, and post-booking processes.
• Maintain accurate property, reservation, pricing, availability, and guest information.
• Stay current with Lodgify features, integrations, API capabilities, and platform updates.

End-to-End Workflow Automation

Design and optimize automated workflows covering the entire guest journey:

Inquiry → Quote → Booking → Payment → Confirmation → Pre-Arrival → Check-In → Stay → Check-Out → Post-Stay

• Configure automated triggers, actions, conditions, and messaging.
• Build workflows that automatically respond to booking events and guest actions.
• Automate booking confirmations, payment reminders, check-in instructions, house rules, follow-ups, checkout instructions, and review requests.
• Create conditional workflows based on reservation status, property, booking channel, dates, guest information, and other relevant criteria.
• Identify manual processes that can be eliminated through automation.
• Continuously test and refine workflows to ensure they operate reliably.

AI & Intelligent Automation

• Identify opportunities to use AI to automate, improve, or streamline website and vacation rental operations.
• Use AI tools to support website content, guest communication, FAQs, property descriptions, and other customer-facing content.
• Help design AI-assisted workflows for handling guest inquiries and routine requests.
• Explore AI-powered solutions that can reduce manual administrative work while maintaining a high-quality guest experience.
• Use AI to analyze operational data, identify trends, and surface opportunities for process improvement.
• Evaluate new AI tools and integrations that could improve the business's efficiency.
• Develop effective prompts and workflows for AI tools and ensure AI-generated content is accurate, appropriate, and aligned with the company's brand and policies.
• Understand the limitations of AI and know when human review or intervention is required.
• Work with website and automation tools that incorporate AI capabilities.

Website & Digital Experience

• Support the development and optimization of the vacation rental website using Lodgify and other website technologies.
• Use AI tools to assist with website content, structure, FAQs, property descriptions, SEO content, and guest-facing experiences.
• Help connect website inquiries and booking activity with Lodgify and other systems.
• Ensure website forms, booking flows, tracking, and automated follow-up processes work correctly.
• Identify opportunities to make the website experience more automated and conversion-friendly.
• Troubleshoot website, booking, integration, and automation issues.

API & Third-Party Integrations

• Configure and maintain integrations between Lodgify and relevant partner platforms.
• Work with Lodgify APIs and third-party APIs to synchronize data and automate processes.
• Understand how booking, guest, reservation, payment, availability, and other data moves between systems.
• Troubleshoot integration and synchronization issues.
• Identify opportunities to connect additional tools to improve automation and operational efficiency.
• Work with Zapier, Make, webhooks, or similar automation platforms where appropriate.
• Coordinate with developers or technical resources when custom API or integration work is required.

Guest Communication Automation

• Design automated communication sequences for every stage of the guest journey.
• Create personalized templates using dynamic guest and reservation information.
• Explore AI-assisted guest communication while maintaining appropriate human oversight.
• Ensure automated communications are timely, accurate, helpful, and aligned with the guest experience.
• Build exception handling for situations that require human intervention.

Workflow Mapping & Process Improvement

• Map existing processes from inquiry through post-stay.
• Identify bottlenecks, repetitive tasks, manual processes, and points where information is lost between systems.
• Recommend and implement streamlined workflows.
• Document processes, workflows, integrations, and system configurations.
• Continuously identify opportunities to improve efficiency through automation and AI.

Requirements

• 2–4+ years of hands-on experience with Lodgify, vacation rental software, property management systems, workflow automation, or similar platforms.
• Strong hands-on Lodgify experience is highly preferred.
• Demonstrated experience building and modifying automated workflows.
• Experience working with APIs and third-party integrations.
• Strong understanding of the short-term/vacation rental booking lifecycle.
• Experience with platforms such as Airbnb, Vrbo, Booking.com, Expedia, or similar OTA platforms.
• Experience with Zapier, Make, or comparable automation platforms is strongly preferred.
• Strong practical understanding of AI tools and AI-assisted automation.
• Demonstrated ability to use AI tools to improve workflows, content, research, customer communication, or business processes.
• Comfortable experimenting with new AI tools and identifying practical business applications.
• Strong understanding of triggers, actions, conditions, workflows, webhooks, and data synchronization.
• Ability to troubleshoot integrations and determine why an automated process is not working as expected.
• Strong analytical and problem-solving skills.
• Highly detail-oriented and comfortable working with complex systems.
• Ability to independently research platform functionality and identify solutions.
• Strong written and verbal English communication skills.
• Ability to document systems, workflows, and processes clearly.
• Comfortable working independently and taking ownership of technical projects.

AI & Technical Skills

Must Have

• Lodgify
• Vacation Rental / PMS platforms
• Workflow automation
• AI tools and AI-assisted workflows
• OTA/channel management
• Automated guest messaging
• API integrations
• Process mapping and optimization
• Troubleshooting and testing

Nice to Have

• ChatGPT or comparable AI platforms
• AI website builders
• AI agents / AI assistants
• Zapier
• Make
• Webhooks
• REST APIs
• JSON
• OAuth/API authentication
• Basic HTML
• Basic JavaScript
• Data mapping
• Smart lock integrations
• Dynamic pricing integrations
• Payment platform integrations
• CRM integrations
• SEO and AI-assisted content generation

Preferred Experience

• Experience transforming a vacation rental operation from a largely manual process into a highly automated workflow.
• Experience integrating Lodgify with multiple third-party platforms.
• Experience designing automated guest communication sequences.
• Experience using AI to improve website functionality or customer-facing experiences.
• Experience using AI to automate repetitive business processes.
• Experience with direct booking websites and booking engines.
• Experience integrating smart locks, guest verification, payment systems, dynamic pricing, cleaning platforms, or other vacation rental technologies.
• Experience working with U.S.-based vacation rental businesses.
• Experience managing multiple properties or complex booking workflows.

What Success Looks Like

The successful candidate will help create a seamless, automated, and AI-enabled vacation rental operation where minimal manual intervention is required.

A successful workflow should allow a process such as:

Guest Inquiry → AI/Automated Response → Quote → Booking → Payment → Confirmation → Automated Guest Communication → Pre-Check-In → Access Instructions → Stay → Checkout → Review Request

to move through the appropriate systems automatically, with human intervention only when necessary.

The person in this role should continuously ask:

"What are we doing manually today that Lodgify, automation, an API, or AI can do more efficiently?"

The ultimate goal is to make the operation more efficient, reliable, scalable, and intelligent as the number of properties and bookings grows.

Independent Contractor Perks

• Permanent work from home
• Immediate hiring
• Health Insurance Coverage for eligible locations (for full-time roles only)

Note

• Please click the "Apply" button to complete your application, including the assessment questions, technical check, and voice recording. Your hourly pay rate will be established based on your performance in the application process; submissions with all requirements fulfilled will receive priority review.