How To Optimize Listings At Scale With Custom AI

Uvika Wahi

Updated on:

How To Optimize Listings At Scale With Custom AI

Efficiency and personalization are not just desired but required for success in the short-term rental industry. This requirement, combined with the heady capabilities promised by the spreading adoption of AI, leads to the question: How can property managers use AI to make their operations more efficient while ensuring each listing reflects their unique brand voice? Our free online workshop on March 20, 2024, sought to answer this critical question, offering a deep dive into how to leverage Personalized AI for enhancing multiple listings simultaneously.

This session, a key part of our trilogy on practical AI uses in short-term rental management, provided clear, actionable strategies for developing your own version of ChatGPT tailored to optimize listings in a way that’s both effective and efficient.

Leading the discussion were two notable figures in the industry: Thibault Masson, the strategic mind behind Rental Scale-Up and current Head of Product Marketing at PriceLabs, and Jean-Emmanuel Losi, the visionary Co-Founder of SuiteOp. Together, they illuminated the path to adopting custom AI solutions—highlighting CustomGPT, a game-changer Jean-Emmanuel employed to transform his business, SoSuite, by making short-term rental management smoother and more personalized.

The core of our workshop was to demonstrate how creating a bespoke AI can streamline the enhancement of multiple listings, reducing workload and boosting outcomes. For those who couldn’t join us, we’re here to share the essential insights and takeaways, designed to inform and motivate you towards integrating AI into your business practices for greater efficiency and personalized guest experiences.

Addressing the Challenge of Scaling

In our previous workshop, our focus was on harnessing the capabilities of ChatGPT to not only understand best practices within the industry but also to apply these strategies directly to your operations for improved outcomes.

We explored the multifaceted applications of ChatGPT, emphasizing its potential beyond simple text-based interactions. We discussed strategies for effective communication with ChatGPT, expanding capabilities with ChatGPT Plus, and asking ChatGPT to identify industry best practices and then tailor these recommendations to address specific challenges within your listings. We also conducted live exercises designed not just to teach but to inspire a proactive approach to listing enhancement.

While the insights and exercises provided valuable strategies for optimizing individual listings, a critical challenge remains: scaling these improvements across multiple listings. The issues at hand include:

  • Individual Listing Focus: Many of the strategies discussed are highly effective for optimizing a single listing but may become time-consuming when applied to several properties.
  • Repetition and Efficiency: Applying improvements manually to each listing can be repetitive and inefficient, potentially hindering your ability to capitalize on these enhancements on a larger scale.

Optimizing Your Listings at Scale: Two Effective Solutions

As the short-term rental market expands, the challenge of optimizing numerous listings efficiently becomes increasingly complex. The “Personalized AI for Bulk Listing Enhancement” workshop delved into this issue, acknowledging the impracticality of individually tweaking each listing, especially for property managers handling vast portfolios. 

To address this, two scalable solutions were presented: Adding Custom Instructions to your ChatGPT account and Creating your CustomGPT. 

Adding Custom Instructions to Your ChatGPT Account

The Power of Personalization

Custom Instructions act as a foundational guide for ChatGPT, enabling it to understand and replicate your unique tone of voice across all interactions and listings. This feature allows you to “train” ChatGPT once on your preferences and stylistic nuances, ensuring that the AI maintains consistency, regardless of the volume of listings you’re managing.

Streamlining the Process

By setting up Custom Instructions, you essentially streamline the optimization process. Instead of starting from scratch with each new listing or query, ChatGPT recalls your specified guidelines, applying them automatically. This not only saves time but also ensures that each listing remains true to your brand’s voice, even as your portfolio grows.

Creating Your CustomGPT

Beyond Basic Customization: Tailoring AI to Your Needs

While Custom Instructions offer a layer of personalization, some scenarios demand a deeper level of customization. Creating your CustomGPT empowers you to build an AI tool that’s meticulously tailored to your business’s specific needs and challenges. This goes beyond merely remembering your tone of voice; it involves training the AI on your preferred content structure, key selling points, and even the feedback you’ve provided on past outputs.

The Advantage of Specialization

Creating your CustomGPT allows for specialization in various aspects of listing optimization, from generating descriptive narratives to crafting responses to guest reviews. This tailored AI becomes adept at handling the specific nuances of your listings, learning from past interactions to improve future outputs. As a result, property managers can achieve a higher degree of consistency and quality across all listings, significantly enhancing the guest experience and potentially boosting bookings.

While these solutions offer significant advantages, their implementation is not without challenges. The process of adding Custom Instructions and creating your CustomGPT requires initial effort in terms of training and setup. However, the long-term benefits of having an AI that understands and executes your specific optimization strategies at scale cannot be overstated.

Adding Custom ChatGPT Instructions for Your Rental Business: A Step-by-Step Guide

Setting Up Custom Instructions in ChatGPT

Accessing Custom Instructions

1. Log into your ChatGPT account: Navigate to the main dashboard.

2. Select “Custom Instructions”: Find this option in the settings or menu, depending on your interface.

Defining Your Business Overview

When prompted, describe your business model, properties, target market, and operational nuances. Here’s how:

Business Model: Specify whether you operate directly with consumers, through B2B channels, or manage properties on behalf of homeowners.

Property Portfolio: Detail the number and locations of properties under your management.

Target Market: Identify the main guest segments you cater to, such as luxury seekers, budget travelers, families, or business clientele.

Highlighting Guest Preferences and Behavior

Understanding guest interactions and preferences is crucial. Provide ChatGPT with insights on:

Common Inquiries: Share typical questions or requests from guests to prepare ChatGPT for similar future interactions.

Guest Demographics: Describe who usually stays at your properties and why, to tailor ChatGPT’s communication style accordingly.

Frequent Issues: Discuss common guest challenges to enable proactive problem-solving through AI.

Detailing Property Characteristics

ChatGPT can only sell what it knows. Make sure to include:

Property Types: List the kinds of accommodations you offer, from apartments to unique stays like cabins or villas.

Amenities and Features: Highlight what sets your properties apart, such as special amenities or unique property rules.

Describing Team Structure and Operations

To ensure seamless guest service, outline:

Team Composition: Detail the size of your team and specific roles, particularly those interacting with guests.

Communication Methods: Explain how your team engages with guests, including any property management software used.

Addressing Special Requests and Customization

To anticipate and meet guest needs, inform ChatGPT about:

Customization Practices: Share how you personalize guest experiences and handle special requests, enhancing ChatGPT’s capability to suggest similar enhancements.

Personalizing ChatGPT’s Responses

Communication Style Preferences

1. Tone: Decide between a formal or casual tone, ensuring it matches your brand’s image and the expectations of your target market.

2. Response Length: Choose your preferred length for responses, balancing between brevity and comprehensiveness.

3. Addressing Method: Specify how ChatGPT should refer to your team or company, adding a personal touch to the interaction.

4. Opinions and Neutrality: Direct whether ChatGPT should offer opinions or maintain neutrality, particularly on subjective matters.

5. Language Simplicity: Given the diverse backgrounds of your guests, request simple and clear language to avoid misunderstandings.

Crafting Your Custom Instructions

With the above framework, you can create a detailed profile that informs ChatGPT exactly how to represent your rental business and engage with your audience. For instance:

We manage a wide array of vacation rentals, targeting primarily families and budget travelers. Our properties, located across several key tourist destinations, range from cozy apartments to spacious villas, each offering unique amenities like pet-friendly spaces and accessibility features. Our team, dedicated to guest satisfaction, employs both direct communication and advanced property management tools to ensure smooth operations. We customize experiences based on guest feedback, focusing on dynamic pricing and effective marketing strategies to attract our main guest demographics.

Implementing Your Custom Instructions

Once you’ve outlined your business specifics and communication preferences, input these details into the Custom Instructions field. This setup not only gears ChatGPT towards generating content that aligns with your operational ethos and guest expectations but also positions your AI as an integral part of your team, ready to engage with guests and manage listings effectively.

Custom Instructions vs. Creating Your CustomGPT

Both routes offer unique advantages, designed to cater to varying business requirements and operational scales. Let’s delve into these options to identify the most effective strategy for your rental listings.

Streamline with Custom Instructions

Purpose: Custom Instructions aim to refine ChatGPT’s existing model to better suit your specific communication preferences and content needs.

Flexibility: This method offers moderate customization, allowing alterations in response style, length, and tone according to predefined instructions.

Ideal For: Enhancing the quality of ChatGPT interactions without extending beyond its built-in functionalities.

Community Interaction: While directly sharing custom instruction sets isn’t facilitated by a platform, users can exchange their strategies through other means.

Application Scope: Primarily suited for text-based tasks, Custom Instructions don’t directly support actions outside the digital conversation sphere.

Customize with Your Own GPT

Purpose: Crafting a CustomGPT means personalizing the ChatGPT framework with additional features and functions specific to your needs.

Flexibility: High customization potential enables the incorporation of extra knowledge bases, task-specific enhancements, and advanced capabilities such as web browsing or image processing.

Ideal For: A wide range of applications, from creating educational tools to developing sophisticated solutions for customer service or targeted marketing strategies.

Community Interaction: The existence of a GPT Store encourages the sharing and discovery of custom GPT models, promoting a culture of innovation.

Application Scope: CustomGPT allows for the integration of external data and APIs, facilitating real-world actions and data-driven decisions.

Making the Right Choice for Your Listings

Selecting between Custom Instructions and CustomGPT hinges on several considerations:

  • Operational Scale and Complexity: Larger portfolios with complex requirements may benefit more from the tailored approach of CustomGPT. Smaller operations or those with simpler needs could find Custom Instructions adequately effective.
  • Community Engagement: For those valuing collaboration and innovation sharing, CustomGPT provides a community platform, whereas Custom Instructions is more individually focused.
  • Data Privacy and Sharing: Both options prioritize privacy, but CustomGPT offers enhanced control over how and with whom data is shared.
  • Deep Integration Needs: Enterprises seeking to weave AI deeply into their systems and leverage extensive data analytics will find CustomGPT’s robust customization capabilities indispensable.

Crafting Specialized AI with CustomGPT: Live Examples

In our workshop, we took on the practical task of creating three CustomGPTs—each with a distinct purpose and tailored to streamline and enhance different aspects of property management. Here’s how each CustomGPT was constructed to address specific needs within the rental industry.

GPT #1: Crafting Compelling Listing Descriptions

The first CustomGPT we created was designed to master the art of property descriptions.

CustomGPT Setup:

This CustomGPT was trained to absorb the style and substance of effective property listings. By analyzing examples of listings that previously resonated with guests, the CustomGPT learned to emulate the structural and tonal elements that are key to captivating potential customers.

Input for Customization:

To prime this CustomGPT, we provided it with a selection of high-performing listing examples that showcased the company’s unique selling propositions and tone preferences—highlighting the charm of amenities, property styles, or the special experiences on offer.

GPT #2: Navigating the Nuances of Customer Reviews

Our second CustomGPT focused on managing customer feedback with finesse.

Learning from Examples:

We fed this CustomGPT a mixture of positive and negative reviews, paired with the company’s actual responses. This exercise equipped the AI with insights into the company’s nuanced approach to acknowledging feedback, addressing concerns, and cultivating a positive guest rapport.

Training Material Inclusion:

Further, the CustomGPT assimilated the company’s internal customer service training materials, ensuring its responses were not only informed by past interactions but also in line with established service protocols.

GPT #3: Painting Pictures with Words for Photo Captions

The third CustomGPT we created took on the challenge of generating evocative photo captions.

Style Adherence:

By inputting a library of photos with their existing captions, the CustomGPT was tuned to produce new captions that reflect the company’s branding and style, whether it was to evoke specific emotions or spotlight particular property features.

Visual Description Skills:

While the CustomGPT works with textual information, incorporating descriptive captions provided it with the context needed to accurately and attractively caption new photos, interpreting visual cues into compelling narratives.

The Process Of CustomGPT Creation and Refinement Process

CustomGPT Creation:

We initiated each CustomGPT by stating our goals, leading the platform to query further details—a process as intuitive as a conversation.

Feeding Data:

The workshop demonstrated how to upload essential data like exemplary listings, review responses, and photo captions into the CustomGPT platform.

Customization and Training:

We leveraged the platform’s capabilities to fine-tune the CustomGPTs’ learning, marking up examples with notes that accentuated the company’s style and content preferences.

Testing and Refinement:

We subjected each CustomGPT to real-world scenarios—crafting listings, addressing reviews, and creating photo captions, all the while refining the AI based on its performance to ensure alignment with company standards.

Ongoing Improvement:

Consistently introducing new data was underscored as crucial to maintaining the CustomGPTs’ effectiveness and relevance, adapting to the company’s evolving brand and guest service strategies.


Opting for Custom Instructions or developing your own CustomGPT depends on your business size, complexity, and the depth of AI integration desired. Custom Instructions offer quick wins for smaller scales, while CustomGPT presents in-depth solutions for intricate operational needs. Our workshop’s live examples underscore the power of CustomGPT to enhance property management, providing a blueprint for implementing AI that resonates with guests and drives efficiency. ~Embracing such personalized AI tools is no longer just an advantage—it’s becoming an industry standard.

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