Housing Connector - AI Assistant for housing search experience

Housing Connector - AI Assistant for housing search experience
Timeline

May - August 2026

Role

Design Manager (leading AI style guide creation and co-managing designers & stakeholders)

Collaboration

1 PM, 8 Designers, 1 Lead Engineer, 2 Product stakeholders, Leadership team

Problem

Individuals experiencing housing instability have a hard time navigating the house search and application by themselves, especially when human support is limited.

Solution

An AI assistant that explains housing processes and requirements, provides personalized guidance, and closes the communication gap between the renters and housing case managers.

Estimated Impact
25%

of the case managers' workload is expected to be automated

60%

estimated AI adoption rate

CONTEXT

Housing Connector is a tech for good nonprofit that increases access to housing for individuals most in need by solving financial and resident challenges for property owners and streamlining the housing search experience for residents.

PROBLEM

Support Provided <<< Support Needed

At Housing Connector, case managers are the middleman between renters and property owners, providing support and connections.

On average, 1 Case Manager support 20 Renters at the same time.
1

Case Managers

  • Provide resources

  • Raise funds for renters

  • Review applications

  • Resolve communication and other housing issues

=> Overwhelmed with the amount of work, often take time to respond

:
20

Renters

  • Low digital literacy

  • At risk of homelessness

  • Little experience with housing applications and requirements

=> Need an extensive amount of support in a short period of time

  • Provide resources

  • Raise funds for renters

  • Review applications

  • Resolve communication and other housing issues

=> Overwhelmed with the amount of work, often take time to respond

Case Managers

  • Low digital literacy

  • At risk of homelessness

  • Little experience with housing applications and requirements

=> Need an extensive amount of support in a short period of time

Renters

1

Case Managers

:
20

Renters

CONTEXT

Housing Connector is a tech for good nonprofit that increases access to housing for individuals most in need by solving financial and resident challenges for property owners and streamlining the housing search experience for residents.

Can AI fill the gap by supporting and guiding renters through the house search/application processes when case managers aren’t available?

Based on survey responses from 30+ renters and interviews with 10 case managers…

71%
71%

Renters expressed no concern about using AI for housing support.

100%
100%

Case managers believed AI would be a great additional source of assistance.

AI GUIDELINES & BRAINSTORMING

AI is for basic requests and manual processes only

Although renters and case managers are open to using AI in the house search process, human intervention is still preferred when it's available.

As this is the first-ever AI assistant on the platform, we defined rules and boundaries for how it should (and should not) function.

AI can…

Explain/simplify housing terms

Handle monotonous tasks and basic questions

Recommend relevant resources

Redirect renters to human staff

AI can't…

Predict the chance of approval or rejection

Communicate with case managers & property owners without renter’s involvement

Make decisions on behalf of users

Provide solutions to complex, situational problems

As a co-manager of the project, I led the creation process for the AI components and style guide
DESIGN DECISION #1

AI entry points that get users familiar with AI and actively offer real-time support

Most renters come from a low tech background and are not familiar with AI, so we were considering the most accessible position to place the AI assistant.

Although the app has an onboarding flow to introduce the chat interface to users, actually using the AI chatbot (and remembering it's available) is a different story.

I created some AI entry points placed them across the app where it makes sense:

  • Offer real-time support in specific use cases, instead of letting users go ask for support themselves (they may not know they can)

  • Introduce AI to users throughout the user flow, not only in onboarding

  • Potentially increase AI adoption

DESIGN DECISION #2

Email Draft closing communication gap between renters and case/property managers

A problem that case managers kept stressing is that a lot of renters and property owners are not responsive to emails and messages, and there's a lack of consistent communication.

A designer on the team and I brainstormed ways AI could help close this gap.

"Renter’s own motivation determines how quickly they get housed. There've been renters who replied to me after 2 weeks. Follow-ups take a lot of my time."

— Case manager A

Previous Iteration
Iteration 1
  • Give users the contact info of case/property manager, and users reach out by themselves

  • "Not enough autonomy"

Iteration 2
Previous Iteration
  • Draft and send emails on behalf of renters, using bot email addresses

  • Stakeholder’s feedback: Automated emails between chatbots doesn’t mean effective communication between humans.

  • "Too much autonomy"

Final Iteration
  • AI drafts message and redirects users to Gmail app. Renters still take initiative to reach out.

  • "Just enough autonomy"

  • Email draft deserves its own component instead of being nested in a message.

  • Push notifications (in-app, email, text) to nudge users to reply to messages and stay engaged in the house search process.

IMPACT

Lighter workload for Case Managers and better support for Renters

After testing the design with 12 users and presenting it to stakeholders across the nonprofit, we got some promising results on the performance of the AI assistant.

25%
25%

of the case managers' workload is expected to be automated

60%
60%

users found the AI assistant helpful and would use it in their house search

THE PEOPLE <3

To those who made this happen with me

It was my first time leading a team of 8 designers, and I learned a lot about design and people management. Thank you to the team members who made this project successful, and the stakeholders who trusted us to work on the product's first-ever AI features!

©
Kaylie Nguyen

2026