Overview

Objective

Help investors with one of the most stressful, time consuming, and expensive parts of being a landlord: dealing with maintenance requests. Stessa users spent over $200M in the last 12 months on maintenance. Helping users receive, track, and fix maintenance users is an opportunity to increase engagement, drive more premium subscriptions to increase revenue by paywalling some elements of maintenance management.

Stessa helps real estate investors track rental property performance and streamline operations. One recurring challenge for landlords and property managers is handling maintenance requests, from receiving tenant reports, to coordinating with vendors, to tracking costs. The Stessa Maintenance feature was designed to simplify this workflow and create a transparent, seamless experience for all stakeholders.

I designed dual-facing maintenance feature in Stessa that allows tenants submit requests and landlords track and resolve them seamlessly, simplifying workflows and improving transparency.

Landlords will then receive the request in the Stessa Investor portal and can then edit the status and details, add transactions to track costs, and manage the maintenance request until completion.

Research and Discovery

I conducted stakeholder interviews, user feedback reviews, and competitive analysis of property management tools to learn more about how landlords are currently handling maintenance requests with their properties and tenants.

• Tenants often submit requests via text, phone, or email, leading to scattered information.

• Tracking status, costs, and communication is cumbersome.

• Assigning requests to vendors or maintenance staff lacks a centralized system.

• Investors want visibility into expenses and trends tied to property performance.

Design goals

1. Seamless Tenant Experience – Easy reporting with photos, status tracking, and updates.

2. Efficient Landlord Workflow – Centralized dashboard to view, prioritize, and assign tasks.

3. Vendor Integration – Options to connect with contractors directly or share requests externally.

4. Financial Sync – Automatic expense categorization for accurate reporting.

5. Scalable Simplicity – A design that works for both one rental unit and larger portfolios

Information Architecture

User flows

Conclusion

The Maintenance feature reflects Stessa’s focus on keeping property management simple and practical for investors. By designing around the real needs of small and mid-sized landlords, we built a tool that cuts down on busywork, makes communication clearer, and ties maintenance directly to property performance.

Next steps

In our initial round user research, landlords consistently expressed frustration with managing communication around maintenance requests and tenant issues. To address this, our next iteration of this feature will integrate maintenance requests directly with Stessa’s new in app messaging feature. This will streamline the conversation between landlords and tenants, reducing friction and ensuring that updates, questions, and resolutions all live in one place.

We also heard interest in being able to connect directly with vendors or contractors through the app, as well as the ability to assign or share maintenance requests with maintenance staff. To address this, we’re exploring potential partnerships with vendor networks, which could help generate partnership revenue on each maintenance issue.