Legal aid’s new digital helper takes on housing questions
Bailey B., an AI chatbot that officially launched on the Bay Area Legal Services website February 17, was born of frustration.
The group increased its services by 42% last year and still couldn’t meet the needs of the 100,671 callers who sought legal help.
“Everyone is familiar with the legal justice gap, but it’s different when you’re actually working in the trenches,” says Legal Content Manager Kezia Hill. “Attorneys who are working in legal aid have a heart for this field, we want to help, we just needed to find a way that we could expand our aid.”
Legal Services Corp. figures show 92% of Americans don’t receive sufficient help for their civil legal needs. Many of Bay Area’s callers fall into that category because they didn’t qualify for full representation and couldn’t afford a lawyer.
Bailey B. is one of the first AI-powered legal assistants developed by a nonprofit legal aid organization, and Bay Area managers are hoping it can help fill the void.
“We are simplifying that process with Bailey B.,” Hill says. “It’s going to really make a dent in trying to close the civil justice gap that we are experiencing.”
Bailey B. is free and designed to help tenants navigate landlord-tenant issues specific to Florida law.
The project is a partnership between Bay Area Legal Services and the justice tech firm LawDroid. David Gray, Bay Area’s former business innovation manager, came up with the idea, Hill says. Gray now works as a director for LawDroid.
Hill, a 2020 graduate of Cooley Law School, left a family law firm to join Bay Area Legal Services last spring to fill the newly created legal content director position.
“My premier focus since I started was to create and write the knowledge base for this chatbot,” she says.

Kezia Hill
Bailey B. is more powerful and mission-driven than the chatbots that proliferate most websites, Hill assures.
“A lot of people may be asking, well, what’s so special about a chatbot, they’re everywhere?” Hill says. “What makes it special is the programming that’s gone into engineering the bot.”
Bailey B. can help tenants with common housing issues, such as giving notice of intent to vacate, requesting repairs, and recovering security deposits, a common request.
Carefully curated content and design help the tool deliver legal answers without straying into a forbidden territory of legal advice, Hill assures.
The chatbot is restricted to delivering content that Hill curated.
“So, Bailey B. does not tell you what to do because Bailey B. is not an attorney,” she says. “What Bailey does is direct people to the appropriate resources and lay out what options are available for you.”
Managers chose to focus Bailey B. on landlord-tenant matters first because housing and family law make up about 60% of Bay Area’s requests for help, Hill says. Bailey B. will eventually be expanded to family law and other practice areas, but that will take time, Hill says. In the meantime, it’s freeing up attorneys to aid clients with more urgent matters, including domestic violence and evictions.
From Bailey B.’s official launch January 17 to February 27, LawDroid logged 241 chat sessions. If managers look back to a December 19 “soft launch,” the number of chat sessions rises to 519.
Building Bailey B.’s knowledge base and updating and monitoring it requires a special skill and an abundance of patience. It’s a job Hill thoroughly enjoys.
“It’s a really intricate, time-consuming process to make sure that everything is accurate, it’s easy to find, it’s easy to understand, it has reliability,” she says.
Hill discovered her love for legal research when she was hired, fresh out of law school, as a judicial law clerk for the 13th Circuit.
She discovered a love for explaining the law, and making it accessible to non-lawyers, when she joined a family law firm. She laughs that she occasionally took heat for the length of her client consultations.
“One of my favorite things to do when I was in private practice, besides being in trial and having that excitement, was consultations, because I always find value in educating my clients.”
An English major before law school, Hill says the job has allowed her to combine many of her favorite talents.
“This is an insane opportunity for me to finally be able to incorporate all of my skills,” she said. “I created the logo for Bailey B. I have a very creative side.”
Hill acknowledges that she does not have an extensive background in computer tech, “but I’m a quick learner,” she says confidently.
The project has also reassured her that no matter how sophisticated AI legal tools become, they will never replace a human lawyer.
“The law and interpretation of the law will always require human thinking, human empathy, and human compassion to connect certain dots, to understand context, so that’s not a concern.”













