Madam Sarina Sabdi has been struggling to support her three children on just $500 a month.
The 31-year-old, who was divorced in 2004, works night shifts in a factory on a part-time basis, as finding a full-time position proved to be difficult.
"The interviewers sometimes think that women with kids wouldn't work as hard because of the children, and that we will miss work if the children fall ill," she said.
Voluntary welfare organisation Daughters of Tomorrow (DOT) has joined the Young Women's Christian Association (YWCA) to run a "confidence curriculum" workshop that culminates in a job fair to help women like Madam Sarina.
Last month, 30 women on low incomes started attending six weekly workshops aimed at building their confidence and helping them secure jobs.
Lessons include personal grooming, career goal-setting and resume writing. At the end of the course, participants will get a makeover for a job fair on Aug 1, which organisers are hoping to put together with 30 employers.
DOT founder Carrie Tan said: "The confidence curriculum is designed to get women into a positive mindspace to help them expand their awareness of possibilities in their lives and in the job market."
She added: "Women from these backgrounds tend to have low self-confidence and as they lack access to information and have limited social circles, their world views tend to be rather narrow.
"The workshops are motivational and focus on getting them to think differently about their future and to set goals for themselves."
The YWCA also provides them with meals, transport and childminding services.
Madam Sarina, who was among the first batch of eight women, said: "This class has given me the confidence to face my fear of going for job interviews."
The YWCA and DOT are also trying to encourage employers to be more empathetic towards these women, by getting them to attend a poverty-simulation programme as part of the job fair.
Representatives from human resources or management, for example, will spend three hours dealing with scenarios based on real profiles of poor families, such as deciding how to best spend the little money they have.
So far, there are 18 employers on board, with recruitment agency PrimeStaff among them.
Its managing director Ronald Lee said: "We can do what we can to help secure employment (for these women). There are plenty of job opportunities if one is not fussy."