From investor to entrepreneur to CFO

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.

Nick DeLeonardis is CFO at Dutchie, an e-commerce platform for cannabis dispensaries.

This interview has been lightly edited for length and clarity.

What would you say is the most challenging aspect of a CFO’s job?

You’re constantly weighing where you want to deploy resources. For better or worse, resources are not infinite. And so you have to work within certain bounds while allowing a company to drive towards innovation and push the envelope of what’s possible. It’s a very complex set of considerations as it relates to taking risks and having room to fail, but also being able to maintain your objectives from an operational and organizational sense.

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

Build and broaden your experience across different parts of the organization. Gain a few cycles of experience in an operating role; get that firsthand experience of a customer-facing role, whether it be sales or marketing; gain that experience of working on a technical team—with systems, with product R&D. As you get closer to the customer and the actual execution of the business, your appreciation for that complexity grows. And your credibility in helping shape the strategy of the business while holding those same teams accountable that you’ve worked shoulder-to-shoulder with in the past, just grows in magnitude.

What was a pivotal point in your career?

The first few decades after school I worked in finance, both as a banker and eventually as an investor across a handful of different funds.

What really changed for me, though, was when I moved from being an investor to being an operator and I tried my hand at my own startup. I tried to build a company that was designed to bring hourly workers immediate access to earned wages. And it brought together technology and financial engineering. As I worked with a handful of folks to try to do that, I really began to appreciate what it meant to get close to a customer and the technology side of building that sort of experience.

That ended up as the on-ramp to working for [restaurant management software company] Toast, where I had a number of different roles. I was very fortunate to have the opportunity to build businesses from scratch through acquisition and also at scale. Once I took the CFO role here at Dutchie, I had a much more holistic appreciation for what it meant to run the business at a level of excellence and scale that I wouldn’t have otherwise.

What do you see happening in the cannabis industry in the next couple of years?

Cannabis is fascinating. It’s an incredibly rapidly growing business—one where the business is growing in parallel with tremendous momentum and broad public support, but it also has complex and constantly changing regulations at both the state and federal level. I would characterize it as having very strong tailwinds, the pace and timing of which are very difficult to predict, but directionally, it’s very energizing. We’ll see an increasingly healthy industry through some of that [growth], an industry that gets increasing access to financial services and capital.

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

The thing I always grew up wanting to be was an architect. And for me, at least, that role is super fascinating because it’s the intersection of engineering and building and design. And the opportunity to build is so energizing to me. It was the driving force for what made me switch careers. Ultimately, the ability to help form and to shape an outcome and then see that in a very tangible format is really energizing.