Three facets of the CFO mindset

CFOs need to be gritty, according to insightsoftware’s David Woodworth.
article cover

David Woodworth

· 4 min read

Coworking is a weekly segment where we talk to CFOs and other leaders in the finance space about their experiences, their companies, and the larger economy. Let us know if you are – or you know – a CFO we should interview.

David Woodworth is CFO at insightsoftware, a provider of financial reporting, FP&A, equity management, and other business software headquartered in Raleigh, North Carolina.

This interview has been lightly edited for length and clarity.

You’re CFO of a company that makes software that’s geared to CFOs. How has your experience helped you in this role?

I joined insightsoftware because we sold [software] into the office of the CFO, and the tools that CFOs have are just so ripe for improvement.

Working at insightsoftware forces me and my team to be…working with product management on improving our products for customers…We’re not the voice of the market, but we are a reference point for product. We get to engage with sales and talk with peers about their challenges, what they’re trying to solve, how insightsoftware’s products can be used. It’s…rewarding in terms of our impact on the company.

What’s one skill that you think a CFO absolutely needs to have to be successful?

Grit is such an overused word. But if you’re going to choose one word, to me, it has to be grit, which encompasses everything from finding a way to solve a problem and power through challenges to thinking about how to get bigger, faster, stronger, in terms of a company. And it’s a cornerstone culturally for how a leader can and should think within companies that are going to pursue growth while also mitigating risks. That’s probably the one core competency I look for in every hire, but also look for in other CFOs.

What’s one of your career achievements that you’re most proud of?

I think my greatest achievements…are still ahead of me. But to date, it’s when I was taking a company through a Chapter 11 bankruptcy with a CEO who resigned. I had an offer on the table to go join another company that was not going through those troubles. And I said no, and just kind of buckled down and pushed through the storm.

News built for finance pros

CFO Brew helps finance pros navigate their roles with insights into risk management, compliance, and strategy through our newsletter, virtual events, and digital guides.

We were in and out of bankruptcy in about three and a half months, which is as fast as you can do it. And the new CEO sold off the tech stack for over a billion dollars on low cost and investors were very happy with the outcome. We didn’t lose customers or employees during the bankruptcy process, which is incredibly hard to do. And so it was a positive outcome through a ridiculously challenging process and time.

What advice would you give someone who aspires to the CFO role?

There’s three things in terms of the mindset a CFO needs to have, in my point of view, to really be effective. One is tied to grit, which is to always be willing and never give up until you find a way to do better. So [the] “find a way” mentality would be No. 1.

Second is knowing how to tell the story. We work with nonfinancial leaders every day. How do you tell…a financially driven story to people who may have differing levels of understanding, let alone interest?

And then third would be looking forward. You can’t look forward enough. It’s not just the current quarter, current year…It’s not just a three-year plan. It’s not just modeling something out. It’s thinking through it end to end, from product development to how you’re engaging with customers as a business to hiring ahead for the skills that are going to be needed 12 months from now.

If you weren’t a CFO, what would you be?

I love being outside. I cannot be outside enough…I’d love to be a ski instructor in the winter, and then [an adventure guide] in the rainforest in the summer and spring—something still with people because I love the human interactions and relationships.

News built for finance pros

CFO Brew helps finance pros navigate their roles with insights into risk management, compliance, and strategy through our newsletter, virtual events, and digital guides.