I've tried writing about this before. And as often happens, when I read over old posts, I find them lacking. I can do a better job of explaining things. I'll try to do so this time as well.
What homeless people need, so to best get back into the work force, is a service that can help connect them to employers willing to help the homeless. This service would do three things. First it would find employers who are willing to hire the homeless. Second, it would find homeless people who are able and available to work. (some homeless people have issues that would preclude them from employment, such as addictions and mental health issues). Third it would create a vetting process by which the best candidates for employment would be matched up with potential employers. It's really no different than any other job service, except that it deals with the specific needs and issues of the homeless. There are employers out there who are willing the hire the homeless, and there are homeless people who are qualified and are willing to work. But the unique situation of homelessness often makes it difficult for employers and potential employees to find each other. Most importantly, this service should be provided by real people getting involved and making things happen by getting to know both employers and potential employees. Automation would just not work in this situation.
For homeless people, it would be a great relief to know that the employer they are going to interview with has already been apprised of their homeless status, and that the issue of being homeless is not necessarily going to be an obstacle to employment. Homeless people can than relax enough so to focus on having a good job interview - developing a good relationship with the potential employer - and not wasting time worrying about how to dodge certain questions concerning their homeless situation.
Employers also have certain needs in hiring people, especially homeless people. I imagine most employers don't want to spend a great deal of time finding qualified applicants, neither do they have the time, usually, to learn all the specifics of how to deal with the different homeless types, trying to figure out which would be the best candidate for a job. It would work out much better for them to hear from a knowledgeable third party whom best to hire. And I'm sure most employers would appreciate being told up front by an expert in homelessness, how best to deal with the specific needs of homeless employees, such as scheduling and transportation issues for the employee.
Posting job openings on a board or web site, for any homeless person to find and attempt to apply for is problematic in a number of ways, which I don't think I have to elaborate on. This particular service requires a real person as liaison. Doing so would insure a much higher rate of success, homeless people would be more likely to apply for jobs and potential employers would not be discouraged by any potential negative experience.