As part of Her World’s Women Of The Year celebration, the Her World Hello Possibilities award is presented in collaboration with Singtel and recognises inspirational female game changers who have made it their business to improve the lives of women and society at large through their company’s impact, creativity and clever use of technology.

Jennifer Choi has always been a woman on-the-go. From her career moving through the ranks at Microsoft, to shifting to start-up life with Grab in Singapore and now, delving into healthcare as Chief Commercial Officer of Amplify Health, she juggles a lot – and that’s without taking into consideration her impressive cycling career which only started six years ago during the pandemic. 

At 37, an injury while running turned her to cycling. She became so passionate about the sport that she began racing competitively and, within four years, earned the top honour in Singapore cycling, the Yellow Jersey, which she went on to win again this year. “[Back-to-back winning] is pretty special,” says Jennifer. “I think combined with work being so much harder and the variety of tasks, including a lot of travel, it was just extra, extra hard.” 

Up until recently, Jennifer was Head of AI Product Development & Government Transformation at Grab where she worked with various government agencies to apply AI, geospatial intelligence and data analytics to address real-world challenges, including flood detection, road safety, congestion and infrastructure monitoring. One example was her work with PUB, which uses AI and real-time data signals to improve rainfall and flood detection, strengthening Singapore’s flood resilience. She also spearheaded GrabMaps, which mapped 700+ towns and cities with 50 million points of interest and address data plus over 1.38 million kilometres of street imagery.

At Grab, Jennifer was keen to bring in best practices that she’d learned from working at Microsoft. In particular, she felt it was important to understand the business from its roots.

“When I first joined Grab, I told my boss that I wanted to do an immersion. I wanted to go see what the driver’s experience was like. Because anybody can buy a research report. That might give you insights, but your competitors will also get them. So for me, my biggest insights are always from firsthand, differentiated research. I wanted to create products that make a difference to drivers; I want to live their pain points and not just note the feedback they give.” 

“Basically, he taught us that when you take more value than you create, you fail.” This commitment to creating more value than she takes is what drove Jennifer to her new role as Chief Commercial Officer at Amplify Health, a health technology and platform services company.

“This is where I get to take all of the things that I’ve learned and use that to create an even bigger difference within the healthcare space. So like, how are we able to use AI in a way that’s going to really change the landscape for us in a meaningful way,” she shares.

Before Grab and Microsoft, Jennifer did a stint at Lehman Brothers (during the financial crash, no less), Diane von Furstenberg and even the London Olympics. Her career is what most of us would call “high-flying”, but these days she is looking at her life beyond work.  

“People always talk about balance and ‘having it all’, and if I’m being honest, this is the hard part for me. When you’re always kind of ‘on’, constantly having to produce the best results, you also have to do a lot of your own inner work. I used to have a day off and not be very intentional about how I used it; I’d just continue to focus on my deliverables,” she recalls.

“So the hardest part for me has been to give myself permission to focus on me. I think that is what cycling has given me as a gift as well, in that it helps me to carve out that portion of my morning where I put myself first. And I never used to do that.” 

To that end, Jennifer made sure she took time off before starting her new role, though negotiating for it still felt strange to her. Nevertheless, it means she’s spent the months leading up to her new job solo travelling around the world – cycling for most of it. “I’m so glad that I did,” she says with enthusiasm. “My headspace is just naturally more positive. I spent a lot of time travelling alone, and I think that gave me so much more inspiration.”

“Coming from an immigrant background and constantly feeling like you’re grinding and grinding to get to that place of safety, you lose that ability to relax. And I think this is a problem that a lot of senior executives get to where they can’t see life beyond their next promotion. But it can’t just be about how much impact you make on others if you yourself are not alive and not experiencing joy.”

With that in mind, Jennifer focused on joy in her travels and is bringing her mother and grandmother along for the ride. “I spent some time by myself at Tokyo Disneyland, something I wasn’t able to do in my childhood,” she says from the Busan airport where she was catching a flight to Seoul. “My grandmother lived through the Korean War, and my mother was my inspiration for becoming a working professional. I’m meeting them in Seoul and I’m going to take them to do silly things like cafe hopping. It’s a last recharge for me, to spend that quality time with my mum and grandma.”

PHOTOGRAPHY Sayher Heffernan
ART DIRECTION & STYLING Cheryl Chan
HAIR Grego Oh using Revlon Professional SG
MAKEUP Lasalle Lee using Givenchy Beauty