On paper, the transition from VP to CFO might seem linear. In reality, it’s a shift in identity, responsibility, influence, and mindset. It’s unlikely you’ll wake up on the first day of the job knowing everything, or feeling fully ready to lead.
In the second in our ‘Confessions of a CFO’ series, Pleo spoke with Jothan Webb, Chief Financial Officer at Censuswide. He’s lived this transition himself, and his experiences reveal a truth that many finance leaders can relate to: the CFO role is less about accounting, and more about shaping meaning, confidence, and direction for the entire business.
Read the first article in the series here.
One myth Jothan doesn’t buy into is the idea that confidence arrives with the title. Everyone suffers from imposter syndrome. “You’re never going to feel like you’ve arrived and suddenly know everything.” Instead, he said that understanding and knowledge arrive incrementally.
He added that new CFOs need to accept they might not know everything, and if you do, something has probably gone wrong. The role will always be challenging and might feel uncomfortable, especially in a growth business. Rather than avoid that discomfort, Jothan recommended leaning into it. “It’s something you have to manage as opposed to something that just disappears.”
The CFO role is about more than just finance. It expands into risk, strategy, narrative, and cross-functional influence. But it can also feel lonelier at the top than people expect. “No one’s really there for you, and that’s just the nature of the game,” explained Jothan.
That isolation can also come with stress from every direction, without anywhere to offload it. CFOs might feel like the whole company is their responsibility, but Jothan noted that it’s important to learn that’s not the case.
The key is understanding the difference between what you’re responsible for and what you have no control over: “What you see is the output of everybody’s work, and if the results aren’t where you’d like them to be, that’s not your fault,” explained Jothan. It also means recognising that you can influence a decision without being responsible for one made against your advice.
He explained that a new CFO might see their role as presenting facts, when it’s actually about giving people confidence that you understand what’s happening. And the way to achieve that is to break it down into ways they can understand:
“Nobody cares whether this is the right accounting policy... What does it mean [for them]?”
A crucial element of the CFO role is having the confidence and credibility to challenge CFOs and boards. Jothan explained this isn’t about killing every ambitious idea; instead, it’s about making the financial reality behind them clear.
The CFO role is often about creating order when everything else feels chaotic. Most finance leaders will face a moment where it feels like everything is collapsing around you. In these moments, the CFO becomes the person who steadies the business.
“You’ve got to focus on one step forward, which is staying focused on your cash, and solving the biggest problem first,” said Jothan. He added that the work becomes methodical: addressing problems one at a time while still maintaining controls and the integrity of the business.
Jothan has seen the same pattern across different growth-stage companies. Finance is under-invested during early stages, and the consequences show up later. Teams inherit potentially messy processes, which leaders may try to solve by adding headcount or new tools.
But for Jothan, this approach rarely works. Instead, he recommended focusing on data, processes, controls, and trust in the numbers first. Only once these layers are in place does it make sense to scale, whether that’s people, processes, or new tools. When it comes to AI, Jothan noted that it’s worth bringing in when useful, but only if your underlying data is sound:
“The systems are only as good as the people who are putting the information into the system.”
One tool Jothan has found particularly useful is Pleo. He highlighted how its spend controls and responsive spend management features helped him effectively manage cash flow during difficult times.
The jump from VP to CFO isn't about suddenly knowing more. The shift is learning to operate with uncertainty while helping everyone else make sense of it.
Modern CFOs don’t just report the numbers, but have to interpret them, explain them, challenge decisions, and help everyone else understand what comes next. That combination means the best CFOs aren’t just technically strong; they also need to be calm under pressure and able to steer the business through uncertainty. As Jothan said, “It’s breaking down what you’re responsible for and what you’re not… you can only do the best you can and not let the rest become a burden.”
Looking for more insights from finance leaders? Visit the Pleo blog, and keep an eye out for the next article in this series.