Scaling at speed – lessons from Booking.com's former CFO

In this series, we're speaking to business leaders who've created a real step-change in their industries. These individuals have not only forged remarkable careers but have also made significant impacts that resonate across their fields.

In each interview, we delve into their journeys, uncovering the insights, strategies, and pivotal moments that have defined their paths to success. Join us as we explore the minds of these Step Changers, celebrating their achievements and learning from their experiences to inspire the next generation of leaders.

Olivier Bisserier spent almost a decade at one of the world’s largest online travel platforms until 2019. Here, Olivier speaks to Airwallex about scaling a business at speed, how we are thinking about work-life balance wrongly, and why modern CFOs must be tech-savvy and think like Olympians.

Q: You spent nine years as CFO at Booking.com. What are some of your key memories and takeaways from that time?

A: My time at Booking.com was characterised by rapid growth. The company was already very successful when I joined, benefitting from a favourable economic and technological environment. The internet enabled the unbundling of travel, there were few major online players, and Booking.com had figured out a scalable business model leveraging Google advertising. 

One of my key focuses was identifying potential friction points that could hamper our growth and proactively addressing them. This meant constantly evaluating if our processes, systems, and teams were equipped to handle huge increases in volume. It required a visionary mindset, always thinking several steps ahead.

I also vividly remember our global expansion. We were entering around 20 new countries per year at one point, which meant rapidly setting up local entities, bank accounts, payment flows, and teams. Navigating diverse regulatory environments and ensuring our platform was localised for each market was challenging but crucial for sustaining our growth trajectory.

As technology reshapes industries, how important is it for modern CFOs to be tech-savvy?

It's absolutely essential. Finance has always been a heavy technology user, which only accelerates with advancements in machine learning and artificial intelligence. During my time at Booking.com, we used these technologies to automate many manual processes, like invoice-payment matching, which allowed us to scale efficiently. 

I believe AI's impact will be massive and hard to predict in the future. As a CFO, you need a firm grasp of emerging technologies to envision how they could transform finance and the wider business. This doesn't mean becoming a technical expert, but understanding enough to set the right priorities, lead conversations with other executives, and ensure your finance systems and processes are future-proofed.

Building this knowledge has to be an active, continuous process. CFOs must dedicate a significant portion of their time to staying on the cutting edge of enterprise technology. It's a substantial challenge critical for success in a fast-changing environment.

How can “tunnel vision” be dangerous in a fast-moving business?

Tunnel vision is a common pitfall, especially for finance teams. When you're deep in the trenches of a process, it's easy to lose sight of the bigger picture. You become so focused on executing your piece of the puzzle that you don't step back to ask if the puzzle itself still makes sense.

This can be risky in a high-growth environment, because the business context is constantly shifting. The process that worked perfectly last quarter may be obsolete this quarter. The assumptions that held true last year may be irrelevant this year. As a CFO, part of my job was to constantly scan for these blind spots and challenge my team to do the same.

I always told my team, "The only thing we need to be concerned about is what's going to come next." That meant proactively identifying processes that might not scale, partnerships that could turn sour, or market shifts that could invalidate our strategy. It meant constantly pressure-testing our operating model and asking, "What if?"

The antidote to tunnel vision is a combination of curiosity, collaboration, and adaptability. You have to be intellectually curious, always seeking out new information and perspectives. You have to collaborate closely with other parts of the business, so you can see how your work fits into the larger whole. And you have to be nimble enough to change course quickly when the data tells you to.

At Booking.com, we fostered this mindset through regular cross-functional dialogues, frequent process reviews, and a culture that celebrated smart pivots. The goal was to catch potential problems early, before they had a chance to slow us down. Because in a fast-moving business, even a small bit of tunnel vision can have huge ripple effects.

You've emphasised the importance of scenario planning, preparation, and visualisation for CFOs. Could you elaborate on that?

The role of the CFO is becoming more sophisticated and challenging, primarily driven by the acceleration of change. The faster a business moves, the harder it is to predict the future. That's why CFOs need to become adept at scenario planning, envisioning multiple potential futures for the business and playing out how each would impact finance.

This type of multidimensional thinking doesn't come naturally to everyone. Some people on my team at Booking.com excelled at holding competing visions in their mind, while others struggled when our direction shifted. But it's a skill that can and must be cultivated.

Once you've mapped out the scenarios, the next step is preparedness. You need to prioritise the most likely paths and proactively put the people, processes, and systems in place to capitalise on them. But you must also build agility into your operations to recalibrate resources if the situation changes quickly. 

Underpinning this all is a clear and adaptable vision. As a CFO, your job is to look far beyond the hood of the car, so to speak, scan for hairpin turns, and determine the smartest way to navigate them. Then, you must communicate that vision to your team and the wider organisation, so everyone is aligned. It's a constant process of envisioning, preparing, and adapting that will only get harder as the pace of business accelerates.

What are the key ingredients needed to scale a business successfully?

I like to distil it down to four key elements: customers, cash, business model, and people. To sustain rapid growth, you need to be consistently expanding your customer base. You need sufficient money to invest in that growth. Your business model and processes need to be scalable, usually through automation. And critically, you need people who can evolve their skills and leadership as the company grows from 100 to 1,000 to 10,000 people.  

Scaling is about relentlessly identifying and eliminating any friction in those four areas. It's about building an organisational culture that embraces change and constantly looks for ways to optimise. And it demands a leadership team always asking, "What's around the corner that could slow us down, and how do we get ahead of it?"

At Booking.com, we embedded this mindset into every part of the business. In finance, we were focused on localising our platform for global expansion, automating manual work, and upgrading our systems and processes to be future-proof. The goal was a friction-free experience for our customers and partners, because we knew that even small inefficiencies could be major speed bumps as we scaled.

How important is having a good payments partner when expanding into new markets?

It's vital, particularly for businesses like Booking.com, which deal with a high volume of multi-currency transactions. In our early days of expansion, the fintech ecosystem wasn't nearly as sophisticated as it is today. We had to manually stitch together local banking relationships, payment gateways, and reconciliation processes for each new country, which was incredibly time- and resource-intensive.  

If we'd had access to a turnkey global payments solution like Airwallex, it would have saved us countless hours and unlocked significant growth. The ability to seamlessly collect payments, hold funds, and pay out to local partners in their native currency without worrying about the backend banking infrastructure is a game-changer.

I distinctly remember it took us more than a couple of years to set up a local bank account in one particular country, despite our best efforts. With a partner like Airwallex, that friction would have been completely eliminated, allowing us to scale faster and redirect our energy to higher-value priorities.

I'd say a robust payment partner is table stakes for any business eyeing international expansion today. It's one of those areas where you shouldn't try to reinvent the wheel in-house. Find an ally who can give you maximum speed and flexibility as you navigate new markets.

What's your perspective on work-life balance for CFOs and their teams?

Honestly, I think the term "work-life balance" is a bit of a misnomer, especially for executives. One of my mentors put it this way: your life comprises work, family, and "me" time. When you take on a leadership role, the "me" time essentially evaporates. Your goal is to carve out sufficient family time, because work will expand to fill all available space.

That was certainly my experience at Booking.com. For nine years, I was thinking about the job constantly, even when I wasn't in the office. The weight of responsibility and drive for success were all-encompassing. I deliberately sacrificed "me" time during that period, almost like an athlete training for the Olympics. And I had to be very intentional about protecting family time.

For my team, I tried to be transparent about this reality. We talked frequently about stress management and the need for boundaries around family commitments. I emphasised that long hours were sometimes inevitable but shouldn't be the norm. And I worked hard to create a supportive, empathetic environment where people could raise issues before they snowballed.

Ultimately, CFOs have to lead by example in this area. Be honest about the job's demands, but also show that it's possible to be fully engaged while still present for your family. Build a culture where downtime is respected and mental health is prioritised. And pay attention to your limits, because you can't pour from an empty cup.

Work-life harmony may look different for everyone, but it has to start with self-awareness, intentionality, and open communication. Every leader needs to cultivate those skills, just as much as technical finance expertise.

Finally, you compared the demands of a CFO role to training for the Olympics. Could you say more about that analogy and how it shaped your approach to the job?

Being a CFO at a high-growth company is like being a professional athlete. You're operating at the highest level of your field, under intense pressure and scrutiny. The stakes are high, and the margin for error is slim.

Like an athlete training for the Olympics, you have to be incredibly disciplined and focused. You have to put in long hours, make personal sacrifices, and push yourself beyond your perceived limits. You're not just trying to be good - you're striving to be world-class.

At Booking.com, I adopted many of the same habits and mindsets as an elite athlete. I was religious about my routines from the time I woke up to the structure of my workday. I prioritised sleep, nutrition, and exercise, because I knew physical health was foundational to mental performance. And I was constantly looking for ways to gain an edge, whether that was through new technologies, innovative partnerships, or unconventional thinking.

Just like an athlete has a four-year training cycle leading up to the Olympics, I approached my CFO role with a long-term view. I wasn't just focused on this quarter's numbers, but on building sustainable systems and teams that could power the business for years to come.

This athlete mentality was crucial to my endurance in the role. It gave me a framework for managing the intense demands and pressures of the job. And it kept me motivated to keep growing and evolving, even when the finish line was far from sight.

I'd encourage any aspiring or current CFO to think about their role through this lens. How can you train like an athlete, both physically and mentally? How can you build a world-class finance organisation that supports the business and helps drive it forward? These are the questions that separate the good from the great.