In this edition of our Finance Leader interview series, we sit down with David Pratt, Group Financial Controller at financial technology company Checkout.com.
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With a diverse career as a senior finance executive spanning industries, geographies, and roles, David offers a unique perspective on the transferability of finance skills, the evolution of finance teams, leading transformation, and more.

Thank you for joining us, David. Can you walk us through your career journey to date?

I've had a broad career in finance – from a commercial role at Mars, to a range of financial positions at Vodafone across several regions, to joining Wise Ltd., where I was the 23rd member of their finance team and left four years later when the team had grown to around 120 members.

I’m the Group Financial Controller at Checkout.com, looking after financial operations, financial reporting, revenue management and finance systems - with a team of around 100 people in different locations around the world, from Tokyo to São Paulo and everywhere in between. 

Working across industries and in nearly every type of finance role has given me a unique perspective. I understand the diverse priorities of different teams, the reasons behind the questions they ask, and how to align people around the right outcomes – whether that means just translating between functions or bringing people together to move forward.

Have you found it challenging to transition between such a broad range of roles, or have the skills been more transferable than people might expect?

I’ve found them to be very transferable. If you can see the bigger picture and think inventively and analytically, you will be able to apply your numerical expertise across different areas of finance. Being surrounded by inquisitive people who can help you to see different perspectives will help with that transition into a more commercial role.

Over the course of your career, what are some of the most significant changes you’ve seen in the way finance teams operate?

One of the most notable changes over the last decade has been around data – not just ensuring that the data is accurate but also being able to interpret and communicate data effectively. 

Understanding your financials is important, but what really matters is what those numbers are telling you. For example: Are we pricing correctly for a certain customer segment? What trends are we seeing in merchant behaviour? There’s more of a focus on understanding and interpreting data more than ever, so that data can drive decision making. 

By extension, we’re seeing fewer finance professionals from purely financial accounting backgrounds, because there is just as much value placed on those data analytical skills. This is particularly the case in technology firms, where understanding and making decisions based on the data is so important. 

Another big shift has been ways of working. While there was already a growing emphasis on culture before 2020, the widespread adoption of flexible and hybrid working models since then has accelerated that focus. We’re looking to actively track this through engagement surveys and other tools.

How are you building a finance team equipped with those analytical skills?

Our finance team is in a scaling phase, so our focus is on hiring experienced people with the right skills. With a global shortage of accountants, that includes growing our teams in countries with strong accounting talent to ensure we can access all the expertise we need.

We’re also looking to develop the talent we have. Given the complexity of the payments industry, we provide a lot of industry-specific training through our learning and development platform, and we're looking to develop programmes to support career growth – whether that means deepening data analytics expertise, specialising in tax, or pursuing ACCA qualifications.

We’re also proactively encouraging more movement between teams to help the transfer of knowledge and experience and develop our team members. 

Digital transformation is high on the agenda for most businesses, with our latest survey of finance leaders finding that 'driving and managing change initiatives' is the most time-intensive aspect of the CFO role currently. 

From your experience, having held a ‘Head of Finance Transformation’ role yourself, could you share any lessons on how finance leaders can navigate change initiatives?

In my experience, if you fail to plan, you plan to fail. It’s a cliché, but it's accurate. 

A big part of making any transformation successful is making sure the system you’re putting in place can do what you need it to.  You don’t want to try to reshape the system to fit your processes; you should be selecting a system that aligns with your business from the outset or be willing to fit into the systems operating processes.  Otherwise, you’re adding extra complexity into your business and will never fully realise the benefits.

I would also say that a common piece of advice is to ‘start by securing buy-in from senior leadership’. That is important, but it’s equally critical to engage everyone who will be affected by the transformation, at all levels, and to do so as quickly as possible. 

That means more than just informing them about the change; it means understanding their needs – from the training they will need to how much notice they’ll need to adjust their plans and processes.

According to our latest survey of 500 finance leaders, fewer than half say they have strong working relationships with their C-suite peers. Of course, driving any change project will be difficult without that alignment.

What do you think are likely to be the root causes of this disconnect, and what strategies have you found effective in building stronger, more collaborative relationships?

That’s definitely not the case in every business, but it’s interesting to hear.

In my experience, it can be because finance teams are still perceived as a bottleneck – slowing things down or adding to the workload – because we need to ensure proper controls are in place and the additional work needed for external audits. That can strain relationships.

I think it’s important to help non finance people understand how finance teams operate and why we can’t be viewed as a siloed function. Nearly everything in the business will come through finance at some stage, from payroll to lease agreements to new products. Finance need to be brought on the journey, involved in conversations and to have the right resources in place. 

It goes both ways, and finance professionals don't always understand how everything connects outside their function either. Siloed thinking and limited communication can lead to misunderstandings on all sides. And that’s not something you can fix overnight; it takes time and effort to build strong relationships over time.

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