Every career has a moment where a single yes opens the door to something more. ‘Yes Moments’ is a blog series that celebrate the choices that sparked opportunities and shaped the professional journeys of our people.

Chooake’s illustrious career is a masterclass in passion turned purpose. From advertising to Silicon Valley, and now to the forefront of innovative design in OCBC, each bold pivot stretched him beyond his comfort zone, sharpening new skills and shaping the way he builds high-performing teams.

See how a series of transformative Yes moments led him to become Head of Group Customer Experience in OCBC Singapore and Chief Experience Officer in Bank of Singapore today.

I started my career as an Art Director at an ad agency, but something in me wanted more. Inspired by my brother and sister who graduated from the University of Chicago (my alma mater, I decided to pivot. Over the next five to six years, I taught myself how to code and dove into information design and interface design, starting with advisory workstations.

In 2006, I moved on to Motorola during the era of candy bar phones. We worked on long-term plans to create devices that combined hardware and software innovation — walkie talkies, secret rocker phones, and early multimedia phones that could carry MP3s. This was before Steve Jobs revolutionised the market with the iPhone in 2007.

After Motorola, I moved to Silicon Valley to work at PayPal’s headquarters, expanding international operations across the APEC region. Later, in eBay, I worked on e-commerce unified checkout experiences so that we can enable a better checkout and shipping experience for both buyers and sellers. In 2014, I was close to joining Google, but fate had other plans.

Move to Singapore, Breaking into Banking

At DBS, I built a solid design team that ran independently. The work was demanding while balancing my role as a late father but seeing the team mature and take ownership was incredibly rewarding.

Saying ‘Yes’ to joining Bank of Singapore in 2021 opened the door to a new opportunity. My portfolio extended to additional marketing responsibilities. We transformed the user experience and introduced video backgrounds on login screens and modernised interfaces.

We moved from web-based apps to native iOS apps for faster performance and clearer navigation and built a Customer Experience (CX) lab on the 22nd floor to observe user behaviour and optimise flows.

We also launched a responsive web version in React with dark mode support, aligning all designs with a comprehensive Design Language System (DLS) to ensure consistency.

Beyond product design, our CX & Design team also designed client engagement programmes — from flagship events, podcast, CIO collateral, marketing materials, pitch books, to multimedia content. We collaborate closely with the Chief Operating Officer’s office and cross-functional team.

Outside of work, I maintain strong ties with the design community, including the Design Singapore Board under the Economic Development Board, where we sponsor scholars to study abroad with commitments to work in Singapore.

Our teams are diverse and dynamic: over 50 people split across Experience Design, Client Engagement & Marketing and Digital Marketing & Communication. We focus on moonshot projects like the Unified Client Journey (UCJ) and integrated wealth platforms, blending art and science to deliver exceptional experiences.

Startup Agility Meets Purposeful Design

BOS operates like a startup — doing first and rolling back later. We balance risk and innovation carefully. In traditional banks, simple actions like transferring money between accounts can take up to 12 hours. Our goal is to make experiences like these seamless for customers.

Design is often misunderstood. It is intangible — like love for your child — you can’t quantify it easily. We must play the long game, asking how we want to be perceived: modern, forward-thinking, and innovative. This requires patience and persistence, especially when engaging with traditional boards and bankers.

We continue to push boundaries, building tools that empower staff and clients. With a clear vision and a culture that embraces creativity and entrepreneurship, we are shaping the future of banking — one design at a time.

Every journey starts with a choice. When was the last time you said yes? Opportunity Starts Here.