What's on the CFO agenda? First-hand insights with finance leaders

With extensive experience as a finance leader in several high-growth technology companies, including Skyscanner and Trip.com Group, Barry offers a unique perspective on the role finance teams play in shaping their business’ digital agenda, achieving alignment on digital initiatives, and more.

Digital transformation is high on the agenda for most businesses, with our latest survey of finance leaders showing 'driving and managing change initiatives' is the most time-intensive aspect of the CFO role currently. From your perspective, what role should finance teams play in shaping digital priorities across the company?

Of course, it will vary a lot from business to business. But for Snappy Shopper, we’re a technology business – so the most important decisions we make are about what we're going to build, what we're not going to build, and where we deploy our valuable engineering resources.

The role finance plays in that is in bringing data and insight to the table to help the company make the right decisions consistently – and in holding the business accountable for the quality of those decisions in hindsight. We need to help ascertain what the key value driver is for any piece of technology work, and to ensure that the financial narrative makes sense and plays a role in how it’s prioritised.

But nothing is ever as simple as that; there’s always a strategic overlay. We need to be thinking five years ahead, and often that means taking a leap of faith on something we believe in, even if there isn’t a clear payback in the next 12 months.

Creating space for those things is important, because there have been times where if we’d been too focused on the data or the financial case alone, we might have deprioritised some very successful initiatives that moved the company forward.

It’s important to be able to knit together those two perspectives - bringing the financial context to the decision, while also leaning into the hard trade-offs that are guided by the company’s overarching, long-term strategy.

And when it comes to digital strategy and emerging technologies, how can finance leaders build the confidence to take a real seat at the table in those conversations?

I think its important to spend the time learning about what good looks like. I’ve been fortunate that I’ve spent most of my career immersed in technology companies where digital strategy IS the strategy.

That’s not covered in accountancy exams – but it is absolutely something you can learn as a finance leader.

Find books about some of the best technology companies in the world – the standouts, the ones leading the S&P 500 – that offer insight into how they got to where they are. They’re packed with lessons on how they built their products and made decisions about digital strategy.

There are also more framework-based books that are helpful – ones like The Lean Startup by Eric Ries, which is one we reference and read often in our business. That's not just in our finance team, but across the company – so we’re all talking a common language when it comes to important conversations about digital strategy.

AI is obviously one of the biggest trends within businesses now. How do you see it reshaping the finance function over the next few years, and how are you engaging with it today as a team?

It’s tough to predict exactly when or how the shift will happen, but I think AI will fundamentally reshape our profession over the next 10 years in a way we haven’t seen before.

More manual, routine tasks will be handled by AI, and I expect Finance's role will shift to focus more on adding value in areas of material judgement and building human relationships with people around the business – whether that’s customers, shareholders, or Board members.

We’re already seeing the start of this transformation in some other sectors, but in finance, the disruption is yet to come. There aren’t really any definitive leaders in the AI for finance space yet and we’re still figuring out as a profession how to train AI for finance in ways that truly drive value. Our focus as a team while this remains true is to stay as close to those developments as we can.

Taking ChatGPT as an example... of course, we’re not feeding it sensitive information…but for general advice, like understanding where the risks might lie in a particular decision, every member of our finance team is using it. We aren’t reliant on it, but it is a helpful aid to speed us up – like having an advisor on your shoulder. And it's a great gateway into the potential of this kind of technology and what it could mean for us in the longer term.

We’re also building a strong network of AI startups in the finance and accounting space – that’s where the innovation is happening. Staying close to that startup community is important so that we can be among the first to test new solutions, in a controlled way, and later be one of the first to adopt them when they’re ready to scale within a finance context.

The closer we stay to these developments, the better positioned we’ll be to benefit once the technology is ready for full deployment in our sector.

When it comes to driving digital initiatives, there’s often a significant change component involved. How do you build the right level of alignment and buy-in across the business – particularly at the leadership and Board level – to support that kind of transformation?

In my experience, it starts at the top – with clear alignment among all stakeholders around what you’re trying to do, why you’re doing it, and what the opportunity will be if you get it right.

Establishing that alignment needs to happen before any specific investment discussion, and it isn’t a ‘one and done’ exercise. You need it throughout everything you do - whether it's when you’re raising capital, so you attract investors who share your vision, or when assembling your board or management team. And you need to revisit this consistently, so it stays embedded in the way decisions are made.

When everyone is aligned around the same objectives, it will make those long-term investment conversations easier. External narratives shouldn’t dominate decision making if the company’s goals are clearly defined and aligned at the top.  

That being said, healthy tension should exist – large strategic investment decisions should be difficult decisions. There's no one view that's prevalent or should win in every scenario, it’s always dependent on the individual investment case and business context.

What's important is that the decision-making process is grounded in what's true - guided by logic, data, and a shared view of where the business is headed.

And more broadly, when it comes to building influence across the executive team, how do you approach those relationships to ensure alignment and trust?

I've found that one of the most important parts of establishing trust is being very transparent about the financial context of the company. Providing your peers in the executive team with that ‘why’ will help them to understand the company’s story through a financial lens, which can really help with alignment and also make it easier to disagree and commit.

It’s about getting them familiar with, and empathetic to, your point of view – and importantly, you also taking the time to understand theirs as well.

Then you can go a step further. It's like a staged process: if you jump to the final step without building that foundation, it’s unlikely to go down well. But once that trust and context are in place, you can start to layer in financial guardrails and reporting that aligns with the financial ‘why’ so that the business is all working toward the same financial and operational outcomes.

In your leadership journey, how important has it been to have a wide breadth of experience? Would you recommend this to others looking to step into a CFO role?

Throughout my career, I’ve been fortunate enough to have the opportunity to make sideways shifts – to step outside of my comfort zone and learn new things.

If you break the CFO role into four or five different competencies, most natural finance career trajectories will go deeply into just one. In my case, my depth was in financial reporting and audit – but if I’d just stayed in that box, there aren’t too many CFO roles where that’s the number one thing the CEO is looking for.

If someone is aiming to become a CFO, broadening one’s experience into other competencies will open more doors in the future.

Not every move will be the right one, so it’s important to be mindful about it, but if there’s an opportunity that will expose you to something new that you think is likely to be relevant and valuable to a CEO or Board down the line – then it’s worth gaining that additional experience.

I’ve always seen people show interest in this kind of cross-functional or sideways move. People are curious, and I’ve always seen that as a healthy sign I’ve tried to encourage. But there's a difference between being interested and taking action. I don't often see people go beyond interest to actively pursue it... I think that’s still relatively rare. Those who do make that leap, in my experience, can really benefit from it over the long term.