Kevin Strain went east. His ambitions grew.

In 2012, Kevin Strain moved to Hong Kong to run Sun Life’s Asian business. He had trained as an accountant, worked in investor relations and led an insurance and investments division in Canada. Now the job involved countries with different languages, different regulations and different expectations of a financial institution. Knowing the numbers would get him only part of the way.

His response included a decision about who should lead. He sought local chief executives and senior managers, supported by people from the wider company. The arrangement gave Sun Life knowledge that could not be packed in a suitcase in Toronto. It also required the regional president to accept that the useful answer might already be in the room.

Strain became Sun Life’s president and CEO in August 2021. His route there suggests an interesting qualification for the corner office: experience of being a long way from it.

The help that came before the title

Before Hong Kong, before the executive appointments, there was the question of paying for university. Strain relied on student assistance and help from his grandmother. He completed a Master of Accounting at the University of Waterloo in 1990, having worked co-op terms in accounting along the way.

Years later, when discussing the scholarships he had established, he returned to that experience. He wanted support to reach students who needed it, including students from diverse backgrounds. The connection was practical. Someone had helped make his education possible; he could help make another person’s possible.

That history gives his advice to students some weight. He tells them to succeed at the work in front of them, to seek guidance from mentors and to choose a next role that opens several possible routes. There is room for ambition in that approach, but also room for a career to surprise its owner.

It is advice with an accountant’s appreciation of options. A promotion with only one possible sequel can be a rather expensive narrowing of the imagination.

A wider view from Hong Kong

In his own account of the move east, Strain says Asia changed his appreciation of diverse and inclusive teams. He also writes about mentors who offered opportunities he might otherwise have missed. The career he describes has people opening doors at several points, rather than one determined executive marching through a prearranged corridor.

His five years leading the Asian business put that idea to work across borders. Local leadership helped him understand local conditions. The company could share capabilities without assuming that every market needed an identical version of the Canadian business.

One relationship illustrates the time involved. Sun Life began discussing a bank distribution partnership with Hong Kong’s Dah Sing in 2016. Strain recalled seeing a cultural fit before there was a deal to do. The discussions eventually produced a 15-year partnership, announced in 2023, giving Sun Life access to the bank’s retail customers.

Seven years is a patient courtship by most corporate standards. In Strain’s telling, waiting and moving quickly belonged to the same process: build the relationship, then act when the pieces fit.

The partnership has a street address

There is a less abstract version of that strategy in Jakarta. On January 15, 2025, Sun Life Indonesia and CIMB Niaga formally launched an expanded bank distribution partnership running through 2039. Strain attended alongside regional executives and the bank’s leadership.

The arrangement joined Sun Life’s products with a banking network spanning 102 Indonesian cities. It included plans for digital capabilities, a more personalized customer experience and financial literacy programs. For an international insurer, a local banking relationship supplies something an overseas headquarters cannot manufacture: an established route to customers.

The photograph captures the ceremony, with the executives gathered onstage. The work behind the occasion is less photogenic. Contracts, distribution, training and the daily business of serving customers have to follow the announcement. A long agreement gives both parties time to do that work. It also gives them plenty of time to be judged on it.

The accountant returns with a bigger brief

Strain became chief financial officer in 2017. The remit covered worldwide finance, taxation, capital and investor relations, along with enterprise services and corporate development. It was a return to finance after running a regional business, with a considerably wider view of what the figures represented.

The sequence matters. He had worked both on the financial explanation of a business and on the business itself. A sales channel was something to operate as well as something to describe to investors. A country’s performance came with people, partners and a history.

When he succeeded Dean Connor as CEO in 2021, that combination went with him. The official chronology is tidy: Asia, finance, chief executive. The useful experience lies in the crossings between those jobs. Each changed the questions he could ask in the next one.

One promotion, several new bosses

A year into the top job, Strain wrote about a consequence of becoming CEO that rarely appears in the celebratory announcement. He had gone from reporting to one executive to answering to a board. He described the change as moving from one boss to ten.

He also admitted that listening had required practice. He enjoys talking with people and gets energy from those conversations. Yet people may tell a chief executive what they think the chief executive wants to hear. The title can make a room more agreeable and less useful.

During his transition, he began meeting virtually with small groups of employees across levels, businesses and regions. He continued those conversations after taking office. The purpose was to hear what worked and what needed improvement.

There is a pleasing complication here. An executive can spend years earning the right to speak for a company, then discover that part of the new job is leaving more space for other people to speak.

“Culture is our superpower.”

Kevin Strain · Leadership Reimagined, 2023

Technology needs a seat at the table

His thinking about digital work follows a similar concern with who gets heard. In a 2024 interview, Strain described three ingredients: modern technology, a different way of working and better use of customer data. He regarded upgrading the technology stack as the easiest part.

The harder work involved bringing technology into business decisions. He wanted IT staff to understand the business and business staff to understand technology, with smaller deliverables and more opportunities to test and learn. Customer feedback should reach the people building the service.

This is a revealing priority for an accountant turned CEO. Buying new software creates an invoice. Changing how colleagues make decisions is harder to put on a purchase order.

He saw generative AI offering faster coding, more efficient operations and better customer understanding. Those were expectations about its potential. The organizational task was already clear: give people enough shared knowledge to use the tools together.

The map keeps getting larger

In May 2025, the Canadian Chamber of Commerce named Strain its International Business Leader of the Year. The recognition cited Sun Life’s local relationships and international expansion, including Asia and asset management. The ceremony followed in Toronto that October.

By then, he was talking publicly about the company’s identity as an asset manager as well as an insurer. His 2025 conversation with Amber Kanwar explored capabilities in public markets, private credit, infrastructure and real estate. The range matters because the familiar insurance name can obscure how many kinds of investment work sit inside the business.

It also changes the scale of the decisions on his desk. In September 2026, Sun Life announced an initiative seeking to deploy C$5 billion into Canadian infrastructure over five years. Target areas included digital technology, energy, transportation and logistics.

The distinction between an intention and an investment matters. The infrastructure equity portion depended on changes to the Insurance Companies Act. These were plans with conditions, rather than completed projects. For someone trained to read accounts, the future tense deserves its own careful reading.

Back home, with somewhere to go

In an October 2026 essay following the Canada Investment Summit, Strain argued that the country needed to turn its resources, talent and institutions into completed projects. His emphasis was on execution: predictable conditions, coordination, skills and the ability to build on time. A global career had brought him back to a domestic question. What makes an opportunity ready for investment?

Later that month, his message introducing Sun Life’s refreshed brand and “Making life brighter” tagline returned to the customer: important decisions, retirement savings and financial security. The institutional scale still has to connect with an individual trying to make a choice.

Away from those announcements, he has described a small habit that suits a travelling executive. He likes to explore the streets around his hotel on an early run. He estimates he has done it in at least 50 cities. He is also an Arsenal supporter and enjoys visiting Japan for its food, parks and art.

There is something fitting about the hotel-door departure. A company can put the world on a presentation slide. Strain still likes to go outside and see a little of it for himself.