Do CEOs Really Climb the Corporate Ladder?

The path to the CEO seat is rarely a straight climb. While many leaders work their way up within an organization, others take different routes—some are industry veterans brought in for transformation, others return after gaining external experience, and in founder-led companies, the visionary who built the business often remains at the helm.

To better understand these leadership trajectories, we examined the CEOs of Singapore’s top 20 companies. The patterns that emerge offer insight into how businesses balance continuity, innovation, and strategic change at the highest level.

Climbing from Within: The Internal Successors

In industries where stability and institutional knowledge are paramount, CEOs tend to rise through the ranks. These leaders spend years—sometimes decades—within the organization, gaining deep expertise before stepping into the top role. This ensures continuity, strong stakeholder relationships, and a steady strategic direction.

Examples:

• Goh Choon Phong (Singapore Airlines): With over two decades at Singapore Airlines before becoming CEO, Goh exemplifies the aviation industry’s reliance on leaders with deep operational expertise and a long-term vision.

• Tan Chong Meng (PSA International): Tan’s extensive tenure at PSA International before taking the helm reflects how global logistics companies value leaders who understand industry complexities from the ground up.

This approach is most common in traditional sectors where leadership stability is crucial and institutional knowledge is an asset.

Staying the Course: Founders at the Helm

In contrast, some CEOs are not promoted from within but rather have led their companies since day one. In founder-led businesses, leadership is often synonymous with vision, risk-taking, and entrepreneurial drive. These CEOs play a hands-on role in shaping company culture, strategy, and long-term growth.

Examples:

• Forrest Li (Sea Ltd.): As the founder of Sea Ltd., Li has steered the company’s expansion into e-commerce, digital entertainment, and financial services, demonstrating the agility and ambition characteristic of founder-led firms.

• Zhong Sheng Jian (Yanlord Land Group): Since founding Yanlord Land Group in 1993, Zhong has driven the company’s growth in real estate development, showing how founder-led firms often take a long-term, visionary approach.

While founder-led leadership offers strong continuity and direction, it also presents challenges, as the company’s trajectory is often closely tied to a single individual’s decision-making.

Bringing in a Fresh Perspective: External Appointments

Some organizations look beyond their internal ranks for leadership, bringing in CEOs with global experience or expertise in transformation. This is especially common in industries undergoing disruption, expansion, or regulatory shifts, where an outsider’s perspective can be invaluable.

Examples:

• Piyush Gupta (DBS Bank): Before joining DBS as CEO in 2009, Gupta spent 27 years at Citigroup. His appointment marked a strategic push towards digital transformation and international growth.

• Revathi Advaithi (Flex): Advaithi was appointed CEO of Flex in 2019, leveraging her extensive background in supply chain management and international operations to drive the company’s global expansion.

While external hires bring fresh perspectives and global expertise, they also face the challenge of integrating into an established corporate culture.

Leadership After a Merger: The Integration Specialist

In industries undergoing consolidation, leadership often shifts to someone with expertise in post-merger integration. This ensures operational alignment and the realization of synergies from the combined entity.

Key Example:

• Chris Ong (Seatrium): Following the merger of Sembcorp Marine and Keppel Offshore & Marine, Ong was appointed CEO to lead the integration of both companies into a competitive maritime powerhouse.

Post-merger leadership requires strong change management skills to align corporate cultures, streamline operations, and deliver growth in a newly structured entity.

Returning to Lead: The “Boomerang” CEOs

A less common but notable pattern is the CEO who returns to lead a company after gaining experience elsewhere. These leaders combine deep internal knowledge with external insights, making them well-positioned to drive both continuity and change.

Example:

• Helen Wong (OCBC Bank): Wong started her career at OCBC in 1984 before leaving for leadership roles in other financial institutions. She returned in 2020 and was appointed CEO in 2021, bringing both institutional knowledge and broader industry expertise.

• Tan Su Shan (DBS Bank): After building her career at Morgan Stanley and Citi, Tan rejoined DBS in 2010, rising through leadership roles in wealth management and institutional banking. Her appointment as CEO in 2024 signals continuity in DBS’s strategic direction while benefiting from her extensive industry experience.

This hybrid approach offers companies the best of both worlds—familiarity with internal operations alongside fresh strategic insights.

What This Means for the Future of Leadership

Our analysis of the top 20 companies in Singapore reveals that while internal promotion remains the most common route to the CEO chair, external hires, founder-led leadership, and boomerang CEOs each play a role in shaping corporate leadership.

While the traditional corporate ladder remains a well-trodden path, Singapore’s leading companies demonstrate a variety of approaches to CEO succession. Internal promotions dominate in sectors where stability is key, while industries undergoing transformation often seek external expertise. Founder-led firms continue to thrive under visionary leadership, while "boomerang CEOs" are emerging as a strategic blend of insider knowledge and external experience.

For investors, employees, and industry observers, understanding these leadership patterns offers valuable insights into how companies navigate succession planning, adapt to change, and position themselves for future growth.

Contributed by Se Wei, Co-Founding Partner, Financial Services, and Zachary Mok, Research Analyst at RevUp Consulting.

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