Finalizing Scope & Defining Key Features.
After it was decided that the scope would include allowing users to assign listings, the team and I started working through the different triggers and variables that would be useful for both our landlords and users. We first started noting down the important actions our tenants take from inquiry to contract signing, then did the same for our landlord users.
When a list was created, we also discussed how to differentiate this feature for our free users and our paid users. After discussions and taking the business goals into consideration, we decided to limit the number of automated messages for our free users to help encourage them to upgrade to our paid tier.

Perfecting the Listing Assignment Flow.
The challenge was determining how to allow users to assign listings. While exploring different design options, it became clear that our competitors had avoided this feature due to the complexity of implementation, ensuring users could assign listings easily while maintaining a seamless experience on both desktop and mobile. Another blocker we faced was accommodating the different listing states for each listing within our design.
Our data showed that most of our users access the platform via desktop. Because of this, we prioritized making the assignment functionality as user-friendly as possible on desktop while doing our best to optimize it for mobile. I created 3 design options and decided to perform user testing.

Refining the Flow Through Testing.
Due to time and budget constraints, we conducted user testing with our customer success team rather than end users, using prototypes for each design. Each prototype received mixed feedback, with testing rounds providing valuable insights that guided the final design selection. I ultimately chose option 1 for these key benefits:
- Reduced confusion during testing
- Offered the simplest, most intuitive flow
- Created less friction for users
- Gave us more room to educate our users
Delivering a Seamless Messaging Experience.
The Auto-reply feature emerged through close integration and collaboration with the customer success team. This project highlighted the value of flexible communication, scope, and design—showing how initial plans can evolve significantly. Strong communication and partnership with both development and product teams proved essential to the feature's success.
In the end, we developed an automated messaging feature that shortened response times between landlords and tenants. Follow-up with the customer success team revealed that while exact metrics weren't available, response time complaints dropped by approximately half.