How Grab’s head of AI for government transformation won cycling’s highest honour in Singapore at 41

Juggling a full-time role in tech and training at an elite athletic level is no mean feat, but it’s a balancing act Jennifer Choi has mastered, albeit with her fair share of rough days. As the head of AI product development for government transformation at Grab, Jennifer leads high-stakes innovation across Southeast Asia. At the same time, she’s a top-tier competitive cyclist, recently earning the coveted Yellow Jersey title—Singapore’s highest accolade in the sport.

Born in Alaska and now based in Singapore, Jennifer moved here six years ago when she reconnected with Grab co-founder Anthony Tan, a former classmate at Harvard Business School, to join the company as Head of Product Strategy. At the time, she left her role at Microsoft’s Global HQ in Redmond, Washington for the opportunity. Before that, her unconventional career path included a stint at Lehman Brothers during the financial crash, time in fashion with Diane von Furstenberg, and even working on the London Olympics.

When the pandemic hit, like many of us, Jennifer picked up a new hobby. But unlike the rest of us who eventually gave up on sourdough and fitness fads, she fell in love with cycling—and took it to a whole new level. While managing a high-pressure career and frequent travel, she joined the sport at 37, trained relentlessly and began racing competitively the following year. Within four years of competing, she earned the top honour in Singaporean cycling: the Yellow Jersey in 2024.

What inspired you to start cycling competitively? 

Honestly, it just happened by chance. I never intended to become a cyclist. I always thought of cycling as an expensive, crazy sport. But during the pandemic, I got injured from running. So I started riding and I realised I could keep up with my friends who were riding light carbon bikes, even though I was riding a super heavy steel bike. I got a carbon bike and I quickly realised, I’m actually pretty good at this.

After getting the carbon bike, I had a horrific crash. I broke two teeth and hurt my face. My first thought was: “How’s my bike? Is it okay?” That’s when I realised I really loved riding. 

I’ve been riding for a while now, and there’s something exhilarating about the speed. Most people listen to music while cycling, but I prefer to just focus on the ride. You can hear the speed and feel it as you see the road rushing past you. It’s a unique and freeing experience.

What does Yellow Jersey Winner mean? 

The title I won is for what’s called the general classification. In cycling, like in the Tour de France, each tour has several stages. You can win a single stage, but the real honour is winning overall—that’s what the yellow jersey signifies.

In Singapore, the Cycling Federation organises multiple races across the year, and they track points across all of them. I competed in the elite women’s category and earned the most points over the season. That’s how I won the general classification and the yellow jersey.

How do you manage recovery and your social life?

At my age, I focus more on recovery. When you’re younger, you bounce back faster, but as you age, recovery becomes more important. I sacrifice a lot of my social life, sleep early to wake up early, some days even at 4am for training, avoid alcohol because it delays recovery, and eat clean to fuel my body.

And I’ve had to learn a lot by myself—I’m self-funded, not part of a national federation, so I don’t have access to sports scientists, sports psychologists or traditional support systems. I’ve figured out glycogen storage, recovery science, and fueling through my own research and friends.

How do you juggle work and training, especially when you’re leading up to a big race?

It’s all in the planning. Three months out, I’ll talk to my friends and family and let them know a big race is coming, and it’ll affect everything—my sleep, my social life, my routine.

Leading up to a big race, I wake up at 4 AM, out the door by 4:20, meet my coach to train from 5 to 7 AM, then head into a full workday. I use ice baths, focus on quality interval training, eat clean, and prioritise recovery. It’s exhausting, but worth it.

Tell us about your role as head of AI product development for government transformation at Grab.  

I help governments modernise their public infrastructure management. Essentially I develop AI focused products and tech that helps governments become more efficient and successful. Most people think of Grab as a consumer company but we also leverage our tech for transforming governments and by using AI for public good. I love identifying opportunities to work together and build solutions that create a difference. It also requires a lot of travel which makes training harder for me than most people.

How do you balance cycling with your job?

It’s incredibly hard. I used to manage teams across Southeast Asia and Europe, and travel a lot. That messed with my consistency. I’d bring my bike when I could, but some places, like Cambodia, I don’t want to risk my safety as a solo female rider.

My fitness would go up and down depending on my travel. I’d look back at workouts I crushed and get frustrated when I couldn’t hit the same numbers after a trip. But I learned to be kind to myself. Every time I get on the bike, it feels like a gift, so I make it count.

So much. Before cycling, I used to let bad days at work define me. If I received tough feedback or had a bad meeting, it would completely derail my confidence. But cycling gave me a healthier sense of identity—it made me more resilient. 

In many ways, this “yo-yo” rhythm between work and training has made me mentally tougher. But there are still days when I ask myself, “Why am I doing this? Why am I suffering?” And yet, I keep showing up. That’s what striving for greatness looks like. Top athletes often say that the real work happens on the days you least want to show up—and I relate to that. It’s not glamorous. It’s discipline. And for me, discipline means doing it anyway, even when you don’t feel like it.

How has being an athlete make you a better leader?

If something went wrong at work, it hit me hard. But now, having a second identity through sport has helped put everything into perspective. It’s taught me resilience, patience, and the importance of taking care of myself—so I can be there for others, too.

Cycling has made me a more empathetic leader. I understand what it feels like to face something scary for the first time, or to go through a tough experience. When I see someone struggling at work, I try to draw from what’s helped me get through hard rides or intense training blocks to help them.

For example, when I see a brutal workout on the calendar, I know what’s coming. Sometimes, I get nervous the day before. But I prepare, I rest, and then I just go and do it. During the workout, I break it down into smaller pieces—just one set at a time. And often, those end up being the days I perform best.

That’s taught me something valuable: most of our fear is in our heads. Once you start, it’s never as scary as you thought. Facing that physical and mental pain repeatedly has made me more confident—not just on the bike, but in life. Whether I’m being asked to lead a billion-dollar initiative or take on something new at work, I tell myself, “You’ve done harder things.”

I’ve also learned that it’s okay to step back. After a tough crash, I gave myself the grace to say, “Maybe I don’t want to do this level of riding right now.” That, too, is growth—knowing you can do something, but also recognising when you don’t have to.