ARE finance functions evolving quickly enough to support where Caribbean businesses are headed?

Veteran Jamaican finance executive Gavin Jordan believes it is a question more CEOs and boards need to ask as Caribbean companies expand into new markets, pursue acquisitions, embrace artificial intelligence (AI), and navigate increasingly complex regulatory environments.

While businesses are becoming larger and more sophisticated, Jordan says the finance functions supporting them are not always evolving at the same pace.

Companies that were once primarily domestic are becoming regional. Acquisitions are bringing together different systems, teams, and processes, while technology, increased regulation, and greater demands from boards and investors are adding new layers of complexity.

Yet, in many organisations, the finance infrastructure at the centre of the business was designed for a smaller, simpler operation. Jordan believes the resulting gap could eventually constrain the very growth Caribbean companies are pursuing. “The company grew. The function did not. The team compensated with effort. The effort became the operating model,” said Jordan, as he described a pattern he’s observed over his career.

The signs are not always immediately visible on the balance sheet. Instead, they may show up in finance teams working increasingly long hours, difficult month-end closes, fragmented systems, processes heavily dependent on individuals, and chief financial officers (CFOs) consumed by reactive work.

Talented finance professionals can find themselves spending more time keeping the machinery running than providing the insight needed to help the organisation determine where it should go next.

For Jordan, that is when a finance problem becomes a growth problem.

He sees the finance function as one of the critical platforms on which a business scales. When properly structured, it can support expansion across jurisdictions, integrate acquisitions, attract capital, manage risk, and enable better decision-making. When it is not, growth can create complexity that teams absorb through greater effort rather than structural change.

This perspective is shaped by 25 years in senior finance leadership in Jamaica, the Caribbean, and the United States.

A certified public accountant, Jordan has held six CFO and finance director appointments, including divisional CFO of GraceKennedy Foods, divisional CFO of GraceKennedy Financial Group, CFO of GraceKennedy Foods USA, CFO of First Global Bank, and finance director of Carreras Limited.

He later served as group CFO and group chief operating officer of Cornerstone Financial Holdings and deputy CEO of its US subsidiary, with executive responsibility for Group Finance, Group HR, Group Internal Audit, Group IT, the Project Management Office, the group’s fintech venture, and group-wide transformation initiatives.

Jordan has also led transformation and restructuring initiatives and managed regulatory engagements across Caribbean and international markets. His board experience includes Jamaica’s National Water Commission, Dairy Industries Limited, and the Barita Foundation. He currently serves as a director of Barita Merchant Bank Limited.

A graduate of The University of the West Indies, Mona, Jordan also holds an MSc in Financial Management from the University of London and has completed executive education at Stanford Graduate School of Business.

For Jordan, the finance function has always been more than reporting and controls. It is the platform that connects every part of the business. It touches every transaction, every entity, every jurisdiction, every decision that involves capital. When it works well, the business can see clearly, move confidently and grow deliberately. When it does not, every other function feels the weight, even if no one can identify the source. That conviction, that finance is the infrastructure everything else is built on, is what has kept him in the discipline for 25 years and what drives the practice today.

That experience has also convinced him that strengthening finance functions is only part of the challenge. The region must also prepare the people who will lead them.

According to Jordan, the modern CFO has moved well beyond reporting, controls, and overseeing the numbers. Increasingly, CFOs are expected to advise CEOs and boards, support acquisitions, manage regulatory and banking relationships, evaluate technology, guide capital allocation, and lead transformation.

Jordan believes the Caribbean has strong technical finance talent, but lacks some of the advisory and leadership development infrastructure available to finance executives in larger markets.

For him, the opportunity is to help develop finance professionals into enterprise leaders, people capable not only of understanding the numbers, but of leading teams, influencing strategy, managing complexity, and operating effectively at CEO and board level.

It was this experience, seeing the same structural problems repeat across every seat he held, that led Jordan to establish FrontCFO, a finance transformation and leadership advisory practice based in South Florida, serving the Caribbean market.

The practice works with CEOs and CFOs whose finance functions have outgrown their original design. Its approach brings together two areas Jordan believes should not be separated: transforming the finance function and developing the leader responsible for it.

There is an assumption that an overwhelmed finance function simply needs more people or more technology. Jordan disagrees.

Additional resources may be necessary, but adding people and systems to an inefficient structure can increase cost without addressing the underlying problem. The same, he argues, applies to AI.

As Caribbean companies accelerate their adoption of AI and automation, Jordan believes they must first determine whether the processes being automated are properly designed. AI applied to a structurally weak process does not automatically fix it; it can simply allow the organisation to execute the same flawed process faster.

For Jordan, the bigger issue is whether the infrastructure inside Caribbean companies is keeping pace with their ambitions.

As businesses look beyond their home markets, finance must support multiple jurisdictions, acquisitions, greater regulatory demands, and increasingly sophisticated capital requirements. Boards may also need to look beyond accurate reporting and compliance and consider whether the finance function is designed for the company’s next stage of growth.

Jordan is now taking that conversation beyond his advisory work. He publishes The Tech-Forward CFO, a weekly LinkedIn newsletter focused on finance transformation and leadership and is writing
Buried by Competence: Why the Best Finance Functions Fail, scheduled for publication in 2027.

The book’s title reflects one of the central ideas behind his thinking: Highly competent people can sometimes keep an inadequate structure functioning for so long that the organisation fails to recognise the need for change.

Good people find ways to make things work. They stay later, create workarounds, bridge disconnected systems, and absorb additional demands. Because the work gets done, extraordinary effort can gradually become accepted as an effective operating model.

Until the business grows again.

After 25 years in finance leadership, Jordan is now focused on helping Caribbean businesses build finance functions and finance leaders capable not simply of supporting the companies they are today, but the companies they are trying to become.