This chapter is a conceptual paper that explores the evolving role of women in the workforce, focusing on progress, persistent challenges, and solutions, particularly for working mothers. The chapter aims to evaluate systemic barriers such as cultural norms, discriminatory practices, and the glass ceiling while assessing the effectiveness of flexible work arrangements (FWA) and technology-driven work models in promoting gender equity. The chapter explores research and case studies from Asia and other regions to identify trends, challenges, and opportunities. It highlights how the COVID-19 pandemic accelerated the adoption of technology-driven work models, such as virtual collaboration tools and ICT, fostering flexibility and inclusivity. However, findings reveal persistent gender disparities in access to flexible work arrangements, with men often benefiting more from existing policies, especially in Asia. Key takeaways include the need for organisations to regularly update policies to promote diversity, address employee needs, and create equitable workplaces. The chapter emphasises the importance of collaboration between governments and businesses in establishing family-friendly policies and legal standards. It also stresses the critical role of technology in advancing flexible work practices, supporting re-entry programmes for female workers, and fostering inclusive, future-ready workplaces.