Summary
Maia is an AI agent built into RentalReady, a SaaS for professional property managers operating in the short-term rental and hospitality industry. This project shows how I lead design in a lean product environment: moving quickly from concept to release, working closely with engineers, and collaborating directly with stakeholders and users to guide continuous improvement.
Guest communication at scale is expensive and it doesn't follow office hours. In Q2 2026 alone, guests opened 261,496 conversations with 2.47 million messages, and the same topics keep repeating: door access, missing payments, missing check-in instructions.
AI agent Maia handles guest conversations, creates maintenance tickets, runs quality audits and sells late check-ins. It cuts down the handoff friction between Support, Operations and Finance, minimising context switch and high volumes of repetitive requests. It also handles troubleshooting when a guest is stuck in front of their door at midnight.
I led design on this project from the pilot in early 2024, starting as a team of three with one engineer and the CTO. Designing an agentic interface in 2024 was a new design challenge, with immature technology, a short deadline, and few established patterns to borrow from. The core design problem was how much control to give users over an agent that acts in their name and talks directly to their guests. Users can configure one or more agents, each with its own tone of voice, scope and instructions, and audit everything the agent has done. To catch failures early, we built reporting into the inbox, a Slack alert on every report, and an audit page visible to both us and the customer.
Four months after launch, I planned and facilitated two AI strategy workshops with stakeholders across the business, including the CEO, CTO, Product Director, and others. I processed the output into six opportunity areas and shared them with the stakeholders shaping the product roadmap. By summer 2026, five of the six had shipped, including Maia's ticket creation from conversations, which today auto-flags around 92% of all tickets in the system.
The project proved its impact in Q2 2026, when Maia's coverage increased from 38% to 54% of reservations in a single quarter, while the guest communication rating increased from 4.58* to 4.71* out of 5*.
Today, Maia is one of RentalReady's main selling points, enabled on 5,781 properties at a flat rate of €5 per property per month, generating around €350,000 in 2026.The difference between a useless chatbot and a reliable AI agent is massive. The project led me to create a set of ethical design principles for AI, now established within our product team, and to publish an article on designing conversational AI that builds trust. The position I argued for, disclosing to guests when they are talking to AI, became a legal requirement in the EU in August 2026. Ethical AI is not a one-time audit: new models are introduced, regulations change, users adapt, and new needs emerge, which is why monitoring and continuous improvement are essential when designing AI products.
of reservations covered by agent Maia
guest communication rating, out of 5*
5,781
properties, 49% of the platform
×
€5
per property, per month
=
≈ €350,000
generating in 2026
What makes Maia agentic
Since launch in 2024, constant monitoring and model improvements have expanded what Maia can do. The feature is now owned by a Product Owner and two dedicated engineers, with PMs working directly alongside the support teams.
WITH GUESTS
• Reads the full context before replying: internal staff notes, conversation history, live reservation data, property detail such as amenities, access instructions, cancellation policy and house rules, and the listing photos.
• Answers in the guest's language, and monitors guest mood. If the mood turns bad it acts on it, for example disabling the review request or forwarding to a human.
• Works alongside humans. It never sends a conflicting reply while a colleague is drafting, escalates complicated or sensitive requests in time, and summarises the thread so the person taking over does not start from nothing.
• Flags conversations into categories: Urgent, Maintenance, Finance and Needs human support.
• Sells. Stay extensions, early check-ins and late check-outs: Maia checks availability and pricing, then sends the guest a payment link to complete the booking themselves. It also nudges open inquiries towards a completed booking.
• Replies to guest reviews.
WITH OPERATIONS
• Creates tickets from mailbox messages and guest reviews, categorises (maintenance, plumbing, cleaning, payments, missing instructions) and assignes to the right person or team.
• Runs property audits that read conversation data, ticket history and review content, turn them into actionable findings, and open tickets from those findings.
Designing configuration for an agent
Designing an agentic interface in 2024 was a new design challenge. Agentic UI had not been seen yet, and there were no established patterns to follow. I approached it by relying on proven design principles, such as Jakob Nielsen's Usability Heuristics (1994), while advocating for ethical design decisions. When there is no pattern for the new thing, the fundamentals still hold.
User control and freedom
Maia is not a simple chatbot but an agent that acts on behalf of users and interacts directly with guests. Customers needed enough control over the agent's scope, through simple pre-defined options, and enough freedom to customise prompts to the point they trust the agent to do the work.
Consistency and visibility of system status
The configuration page uses our existing design system, so it is learnable and easy to adopt. Users can see at a glance which agents are enabled and what each one covers. Visibility does not stop at setup: what Maia actually did, and why, is visible on the page for auditing Maia's output.
What can be configured
•One or more agents, each with its own scope
•Which conversations Maia replies to, scoped by reservation status
•Which categories are flagged, and which escalate to a human
•Tone of voice
•Signature
•Special instructions in free text
•Per-property configuration
•Whether inquiry chasing is active
•Whether upselling is active
Outcome
54%
of reservations covered by Maia AI
5,781
properties, 49% of the total
815k
messages sent by Maia to guests in Q2 2026
92%
of all tickets auto-flagged by Maia, 41,300 of 44,700
The project proved itself in Q2 2026, when Maia's coverage rose from 38% to 54% of reservations in a single quarter and the guest communication rating rose with it, from 4.58* to 4.71* out of 5*. Thanks to Maia, the human response time is now 12 minutes, down from 22 minutes.
Today Maia is one of RentalReady's main selling points. It is enabled for 5,781 properties, 49% of the platform, at a flat rate of €5 per property per month, generating around €350,000 in 2026.
Maia was the first AI agent built directly into a PMS as a feature, not a third-party tool or integration. Two years on, the quality of its answers is significantly ahead of what competitors offer, because it handles complex flows, is customisable, and works on the customer's own data rather than on a generic knowledge base.
What started as three people, a designer, a CTO and a software engineer, became one of the business's strongest commercial assets, and a tool that saves customers real time on guest support. It also earns them money through upselling, stay extensions and inquiry chasing, and it catches problems inside the property by turning what a guest says into a ticket for the team that can fix it.
Ethical AI is not a one-time audit: new models are introduced, regulations change, users adapt, and new needs emerge, which is why monitoring and continuous improvement are essential when designing AI products.