“There is an art form to managing the CEO-CFO relationship” – Jonathan Dent

Sydney-based CFO Jonathan Dent reflects on five years in the role at high-growth start-up DesignCrowd.

Jonathan Dent has an inquiring mind, and thus he began his Arts Degree with an eclectic choice of subjects: Chinese language, philosophy, psychology and physics. However, after completing his first semester, he realised he needed a total rethink. What did he actually want to do when he finished university, and what kind of a degree would help him get there?

Dent took some time out to mull over his career goals and worked at a couple of different organisations, including a full-time job in accounts payable at payments solutions company Cuscal.

“Doing data entry was not the most fulfilling role, but I loved the organization,” he says. “Team morale was strong and everybody got along and hung out together outside of work. The team always pitched in and there was a lot of internal movement with promotions and people moving across departments.”

He also came to realise that what interested him most was running a business – whether it was owning that business or being part of a management team. With a renewed sense of purpose, Dent began a commerce degree at the University of Sydney. He kept in touch with his former colleagues at Cuscal and when he graduated in 2004, he was offered an entry level management accounting role.

Disrupting bricks and mortar

Within a few years, Dent was managing FP&A and ultimately went on to become the company’s financial controller and head of finance. He remained at Cuscal for another six years before he was snapped up by DesignCrowd as its CFO in 2017. Dent was eager to work at a start-up that was disrupting traditional bricks and mortar business models.

“It was also an opportunity to really roll my sleeves up and get involved in a company at a much earlier stage,” he says.

DesignCrowd is a crowdsourced logo, freelance graphic and web design business. It helps small businesses in particular access design skills in a way that is more affordable and accessible. Its newer DIY design subscription business, BrandCrowd, was launched three years ago, and business has doubled in the past 12 months.

“We’re expecting high double-digit growth for the next few years at least,” says Dent.

There are certain challenges that come with being the CFO at a high-growth business. For one, it requires an adaptive mindset.

“As we scale up, it is important to switch from defensive thinking into growth thinking,” he explains. “They are very different mind frames. As you get into that growth phase, you really need to think about the impact of the decisions you’re making early on, and understand their impact in three months, six month and two years. When everything’s going well, it is easy to start spending huge amounts on team and marketing. You can create problems down the track.”

“You are always at the table”

Dent has been in the role for five years and he see the functions of a CFO continuing to evolve.

“Twenty years ago, a CFO was someone who was planted alongside the business. I think the boundaries have become fairly fluid and the CFO is highly integrated with leadership colleagues. The modern CFO is part of the decision-making process: you are always at the table and always part of the conversation.”

However, he believes that the traditional role of stewardship remains as crucial as ever, and this is particularly true in current volatile market conditions. “For the last few years, things have been so up and down that being the trusted person who focuses on what’s best for the business is really critical.”

One of the aspects of the CFO role that Dent loves is the multi-discipline responsibilities, such as liaising with finance, HR and legal. Dent frequently deals with lawyers to discuss aspects of intellectual property, fundraising, copyright and trademarks as it relates to DesignCrowd and BrandCrowd. He is comfortable in the cross-over with these legal disciplines because he completed a part-time postgraduate law degree in 2019.

“I’d been working in finance and accounting for a long time and I wanted to use another part of my brain. I started it not thinking that I would necessarily finish it. Then at some point, I started enjoying it. It developed a momentum of its own.”

“It was probably a very long and expensive way to exercise a different part of my brain,” he adds with a laugh.

The hunger to learn has never left Dent and he may return to do further study at some point in the future. For now though, he has a full plate at work and with two small children at home.

“Being a dad has taught me to put boundaries around work. It’s easy for work to creep into every spare second that you have. However, kids have a wonderful way of forcing boundaries on you because there is a period during the evening when there’s absolutely no chance of getting a minute of work done!”

Navigating the CEO-CFO relationship

In a high growth environment, the CFO may potentially need to disagree with the CEO for what they believe is the good of the business. Dent acknowledges that there are inherent challenges and that maintaining a positive dynamic takes a certain skill and maturity.

“A CEO is often more product focused, more visionary, and more optimistic than a CFO. There is an art form to managing that relationship. First of all, the ability to say no is important. Some people just don’t have it, because they don’t want to get into a disagreement.”

But even more important is choosing the right battles, he says.

“If you disagree on every single point, it just becomes noise and your views are ignored. And if you argue all the time and don’t do it in a way that’s respectful to your colleagues, then you’ll never get anywhere and the relationship with the CEO can break down. I’ve seen that happen to colleagues over the years.”

When an idea is pitched to Dent, his first instinct is to say no. Over time, he has learned to “park” that voice while trying to understand all the potential benefits.

“I don’t like to admit it, but my natural mindset is to see all the problems. For me, learning to overcome that has been critical to my success in the role.”