Never too late: Microsoft, Generation Singapore help mid-career job seekers pivot to tech

woman looking at computer monitors

Stepping out of her comfort zone was a big decision for Nelly Lee. The Singapore native and single mother built a successful 20-year career in the travel industry, where she was considered an expert in her field. Still, Lee felt the urge to reinvent herself, one that was accelerated by the global disruption of the travel industry in the aftermath of the pandemic.   

“I was thinking I should give myself a chance to see I could do something different to take care of my daughter and my parents,” Lee said. “Yes, in my previous job, the knowledge and stability was all there. But I wanted to show myself that even though I don’t have a degree in tech, that didn’t matter.”  

Changing careers mid-stream can be tough for anyone. There’s an even higher degree of difficulty when moving into the technology field, where other applicants and co-workers have years of knowledge and hands-on experience. Generation Singapore wants to help level the playing field so everyone has a chance at a better career.   

In 2020, Microsoft and Generation Singapore co-created #GetReadySG, a national skills initiative in partnership with several Singaporean government technology organizations. The initiative is designed to upskill and/or reskill up to 1,000 job seekers over a two-year period and then match them with meaningful employment opportunities in tech. The program is designed for young professionals and mid-career switchers who want to gain in-demand digital skills at a subsidized cost.  

As Lee considered making her career change, she learned about Generation Singapore. She consulted with her brother, a software engineer, before her second interview to find out more about the program. Soon after, Lee was admitted into #GetReadySG, where she began learning skills that would benefit her move into the tech sector.   

“When I got into the course, it was so alien to me,” Lee recalls. “I didn’t know what a virtual machine was. I would screen share with my brother to help me get a better understanding. I’d ask him, ‘What is this?’ ‘What is that?’ But I started to slowly digest things.”  

In addition to the classroom work, Lee learned valuable skills during her internship, which all participants in the program must complete.   

“This program is very different from others where you take a course and at the end of the day you go and search for your own job,” Lee said. “Because of the apprenticeship you get a six-month chance to learn and adapt to the working world.”

A woman stands in front of an apartment building
Nelly Lee decided to switch careers in order to make enough money to eventually buy a new home for herself and her young daughter. Photo by Ore Huiying for Microsoft.

The #GetReadySG program also provides participants with the opportunity to be mentored by tech industry professionals as they approach the start of their internship and plan for full-time work. Lee was paired with Sindhu Chengad, an Azure and Open Source business leader in Microsoft’s Singapore office, and they developed a relationship that proved valuable for both parties, especially because it can be difficult for women to have female role models.   

“We’ve been working together for the last six months,” Chengad said. “I know how challenging it can be to keep a career on track, and I’ve always found it helpful when people have taken a chance on me and helped guide me. Nelly’s story is such an inspiring story. For a mom to think about disrupting her own career to come into a completely new space and to upskill yourself is super challenging. I’m super proud of where Nelly started and where she is today.”  

As Lee worked through her internship, she set her sights on a full-time job, one in which she could earn a better salary with the goal of moving into her own home. She quickly landed a DevOps position supporting a large international technology company that allows her to work from home and take on a variety of technical challenges. 

“I wanted to do something more technical because I find it more interesting,” Lee said. “I do a lot of server work, deployment, fixing bugs. There’s still a lot of learning going on. But my team is very patient and they explain many things. It’s very comforting and it makes me feel like I can contribute more.”  

The #GetReadySG program has placed hundreds of graduates in several tech companies throughout Singapore, giving well-trained individuals a chance to fill the gaps in human resources that many companies in the country have been dealing with over the past few years.   

“There’s a tremendous amount of commitment and resilience that every graduate brings into this program. It’s indeed a tough journey to break barriers in switching to a new career, that’s why I’m really proud of them,” said Prateek Hegde, CEO of Generation Singapore. “We might have a well-designed program and supported them all the way, but majority of the credit goes to every individual who persevered throughout every process and gave their best. I hope to witness more women follow Nelly’s footsteps.”  

For Lee, the decision to switch careers was life-changing, and she urges others in her position to consider betting on themselves and learning the skills needed to enter the tech industry.   

“This is totally out of what people think of me,” Lee said. “Many people didn’t think I would make this step. But I am very happy. It’s an achievement for myself.”  

Top image: Nelly Lee took advantage of GetReadySG, a national skills initiative co-created by Microsoft and Generation Singapore, to retrain for a career in technology after 20 years in the travel industry. She now works in DevOps supporting a large international technology company. Photo by Ore Huiying for Microsoft.