Tony Cheng and the education that never ended

Long before Tony Cheng was responsible for a reinsurance group, he was responsible for giving people their change. At his parents’ sandwich shop in Sydney, the future chief executive worked the register. A small business offers a fairly direct introduction to commerce: somebody orders, somebody pays, and the arithmetic has to work before the next customer arrives.

Today Cheng is President and Chief Executive Officer of Reinsurance Group of America, Incorporated, known as RGA. The amounts have changed. In 2025, the company generated $23.7 billion in total revenues. Yet his accounts of his career keep returning to the work of learning a business, making decisions with other people, and discovering how much a new assignment still has to teach him.

There is something pleasingly unglamorous about that continuity. The sandwich counter survives in the biography alongside the board appointment. It gives the qualifications and promotions a place to begin.

The register came first

Born in Hong Kong, Cheng moved to Sydney when he was nine months old. His parents ran small businesses, and their four children helped. His own childhood ambition included buying his parents a house. Business, in this telling, had a family attached to it before it had a corporate title.

His brother supplied the actuarial career pitch. Cheng recalled being told that Australia had only six actuaries and that all of them drove Ferraris. Treat that as an older brother’s memorable sales technique. It is an anecdote about persuasion, rather than a dependable census of either actuaries or Italian sports cars.

Cheng was good at mathematics and chose the profession. The commercial ambition remained. By 2019, when his responsibilities extended across RGA’s Asian business, he said he still put “actuary” on immigration forms. The label had proved more durable than his job descriptions.

“Being an actuary is still very much a part of me.”

Tony Cheng, 2019

An apprenticeship with a passport

Cheng joined RGA in 1997 as chief actuary of Malaysian Life Reinsurance Group Berhad, its joint venture with the Life Insurance Association of Malaysia. His subsequent career would connect regional assignments with the company’s Missouri headquarters. It was an education conducted inside the business as well as in a classroom.

He earned a Bachelor of Economics at Macquarie University in Sydney, followed by an MBA at Washington University in St. Louis. Olin Business School identifies him with its Professional MBA class of 2002. That same year, he relocated to Hong Kong.

In 2004, he became chief executive of RGA’s Hong Kong office, with responsibility for Hong Kong and Southeast Asia. In 2011, he became Senior Vice President, Asia. The expansion in responsibility is visible in the geography: one office, a group of markets, a region.

A career chronology can make those moves look inevitable. Years between appointments disappear into the space between two dates. Cheng’s later advice is more useful than that tidy appearance. He has described a mentor encouraging him to try the Hong Kong actuarial assignment, and has identified that move as a turning point. Somebody else’s confidence helped him take the next step.

The useful discomfort of another question

Cheng had been writing about learning well before becoming group CEO. In a 2018 essay, Tara Westover’s memoir Educated prompted him to consider the force of self-education. He also recalled once imagining that he might become RGA’s Head of Asia, a goal that had initially seemed improbable to him.

His practical method involved asking several questions until he understood the underlying problem. He worried about what people miss when they ask too little. Requesting a colleague’s help could feel exposing, he acknowledged, but it could also prevent an error.

“True collaboration requires the courage to speak and the patience to answer,” he wrote. That sentence distributes the work rather fairly. The person who asks has a responsibility to engage. The person who knows has a responsibility to stay in the conversation.

There is an appealing lack of ceremony to the method. It can happen at a desk or in a meeting, without waiting for the next qualification or promotion. It also makes experience available to someone beyond its owner. A colleague’s explanation becomes part of another person’s education.

A room with more than one answer

In a 2019 video interview, Cheng described bringing together people from different regions and specialties so that debate could produce useful conclusions. For an executive whose own assignments had crossed markets, the argument was concrete. A global company already contains different perspectives. The organizational task is to let those perspectives meet and do useful work.

He had made a related point at a European insurance conference in 2018. Preparing the next innovation, he argued, required a commitment to research and development, dependable data, specialist talent and collaboration. He also spoke about being willing to fail. The ingredients extended well beyond a clever proposal.

By May 2023, as RGA’s new president, he was describing a companywide effort to articulate its values and competencies. Input came from across the organization, including senior executives, as the business worked on a five-year enterprise strategy.

Read together, these remarks give substance to his interest in learning. Questions matter at the level of the individual. Debate matters at the level of the team. Listening across a company can inform the way it organizes itself. The scale changes, while the obligation to hear another person remains.

Twenty-seven years to the top job

By the time RGA announced its succession plan in January 2023, Cheng was Executive Vice President, Head of EMEA, Asia, and Australia. He had accumulated responsibility across a substantial part of the group’s international business. The board appointed him president and a director effective January 4.

Anna Manning remained chief executive through the end of that year. Cheng took over on January 1, 2024. The announced transition gave the two leaders a year in their respective roles before the handover.

In accepting the appointment, Cheng acknowledged both Manning and her predecessor, Greig Woodring. His comments emphasized the culture and business they had helped build. Manning, in turn, pointed to his client focus and the regard in which colleagues held him.

The sequence matters to the story. After roughly twenty-seven years inside RGA, Cheng was taking charge of an institution he had experienced at several levels. He knew it as an actuary, an office leader and a regional executive. The new title gathered those earlier jobs into a much larger responsibility.

What $32 billion actually describes

One measure of that responsibility arrived on July 31, 2025, when RGA completed a transaction with Equitable Holdings to reinsure a diversified block of life insurance products. The announced amount was $32 billion. It described the block being reinsured, and should be read with that definition attached.

The agreement also widened the companies’ partnership across underwriting, product development, distribution and investment management. Those details help explain why a reinsurance announcement can reach into several parts of a client’s business. Transferring risk is accompanied by decisions about products, capital and the relationships needed to support them.

Cheng presented the closing as an example of working with a client on a transaction intended to support growth and longer-term value. The language belongs to a business whose work often happens behind another insurer’s name. Most readers will recognize the insurer that sold a policy before they recognize its reinsurer.

His 2025 annual-review message gave credit to the operations and support teams behind RGA’s progress. That acknowledgment fits the collaboration he has discussed for years. A transaction headline has room for a company name and a number. Completing the work involves many more people.

The financial reporting continued into his third year as CEO. On August 6, 2026, RGA reported second-quarter net income available to shareholders of $462 million, or $7.01 per diluted share. It is a dated result, one entry in the continuing record of a business that must keep delivering after an appointment or a deal has left the news.

Keep giving

When Cheng returned to Olin to speak with students, he later shared three themes: “Keep Going,” “Keep Growing” and “Keep Giving.” His account connected persistence with learning, then connected leadership with responsibility for other people. A promotion, in that view, increases the number of people whose development you can help.

The final theme adds something to the familiar advice to stay curious. Learning can be personally rewarding; giving asks what someone else receives from it. The mentor who encouraged his move to Hong Kong offers a small, practical example of that exchange.

There is another possible career in Cheng’s imagination. Asked what he might do outside his profession, he chose food and restaurant criticism. He likes discovering food from around the world and would enjoy sharing those discoveries.

It is a cheerful alternative ending for a career that began in a sandwich shop. For now, the work remains reinsurance, with its long commitments and large numbers. But the register, the classroom and the conversation with a helpful colleague still belong in the picture. They explain how Cheng got here, and why he keeps talking about what there is to learn.