Dorothy Oskar’s journey in the technology industry started early in her life when she was recruited by the National Computer Board (NCB) right out of her computer science studies in Australia. Excited by the opportunities to learn new processes in various domains, Dorothy has been a part of the NCS team ever since. Dorothy now serves as Head of Business Application Unit, NCS. She played a large role in the Singapore government's push towards civil service digitalisation by harnessing technology to improve public service’s operation and customer service efficiency. She recounts her experience in designing and implementing systems in law enforcement to prevent white-collar crime as well as developing HR and payments systems for the civil service as some of her works that saw through her growth. Having worked on multiple government projects, Dorothy finds deep satisfaction in having helped the public sector in Singapore, seeing how it has been recognised for keeping pace with technology, and she wants to do more.

Dorothy believes that while she can continue to contribute at a strategic level, she wants to plan for long-term continuity and impart her experience and knowledge by investing in her team. She believes people development is the way forward and actively coaches up-and-coming talent enthusiastically. For Dorothy, every situation is an opportunity to develop her team, even in the most demanding projects. She wants her team to grow their skill sets, develop mental fortitude, while keeping an open mind to learn and overcome hurdles. This is important as organisations face the harsh demands of market forces and challenging timelines. The next generation of leaders needs to have fortitude and enthusiasm to take on challenging projects and outperform their toughest critics, and Dorothy is nurturing these future leaders with a sense of vision to continue the NCS legacy. Accomplishing this would be another milestone in her role as a leader.

Just as she invests time and effort in her teams at work, Dorothy puts the same energy into the children's choir in her church, which she teaches on the weekends, making sure the choir has the right technique and pitch. Music has always been in her life. Whether she is behind the piano or in front of a choir, Dorothy wants to always keep learning. Her latest challenge for herself is to learn jazz improvisation, something different from the classical pieces she has always been more familiar with. As life throws inevitable curve balls, the ability to improvise according to the situation and seize opportunities can make all the difference. Staying open to new opportunities and different approaches help Dorothy and her teams avoid becoming fixated by any one technology or solution, and this adaptability helps keep them relevant.