CFOs

Coworking John McCauley

CFO of Calendly
article cover

· 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. To be considered, answer a few quick questions for us here and we’ll be in touch if we want to feature you in the newsletter.

John McCauley is CFO of Calendly, a software company that provides a scheduling platform for individuals and teams to align external meeting times with users’ calendars.

This interview has been lightly edited for length and clarity.

How do you think the CFO role has changed over the past five to 10 years, both for you, and in general?

In tech, we are operating with higher levels of transparency than they did 10 years ago. As a result, a big chunk of the CFO’s day is spent in cross-functional situations and telling the financial story of the company.

What’s something we can’t guess about your job from your LinkedIn profile?

I am quite into photography as a hobby. It kind of crosses over to technical and creative. When you work with a camera, you have three fundamental things: ISO, aperture, and shutter speed, and so that’s highly technical in nature. But then there’s also composition and lighting. And there’s so much creativity involved there.

I’ve spent the majority of my career in software startups. And it’s very well known that within a startup, you’re working with imperfect data. We have to make decisions, we try to encompass data in our decision making, we really try to understand things from a pattern recognition perspective, but the reality is we hit situations all the time where there just is no data on that decision point to be made, or there is no way to pattern-recognize. And, in fact, I think you can fall into a trap; if you try to compare prior situations too much to a current situation—I call them false analogs—where you’re looking at a scenario and you’re saying, “Hey, this company I was at prior did it this way.”

News built for finance pros

The latest news and insights corporate finance professionals need to know to keep up with their constantly evolving industry.

The reality is there’s probably nuance in that decision that you’re trying to make. That’s where I think creativity kicks in; you’ve got to be able to think on your toes.

Oftentimes, I think there’s a little bit of a misunderstanding of a finance professional [in] that it is 100% rule-based. We absolutely have to be technical and understand those rules—there’s no way around that. But, in the application of them, there’s a lot of decision-making to be had.

Where I see finance professionals differentiate themselves is the ability to work in that ambiguity. I think that’s the difference between great leadership, and you’re just maybe a great individual contributor.

What advice do you have for future CFOs?

Refine your storytelling. Technical skills are table stakes—the ability to tell your company’s financial story in an understandable and compelling way is a great differentiator.

First and foremost is just getting out there, getting over your fear of public speaking, and being able to hone your craft as a storyteller by just doing it over and over.

Secondly, I put in an exorbitant amount of time in preparation for a presentation, whether it’s in written form, or verbal, you can be assured that prior to me presenting it, I spent tens if not hundreds of hours in preparation, such that by the time you’re ready to publish that thing, or get in front of a group and present it, you know it like the back of your hand, and it almost looks like it’s effortless.

If you weren’t a CFO you would be...?

Photographer or cinematographer. Photography is such a great crossover for me because it encompasses both the technical and creative aspect.—KT

News built for finance pros

The latest news and insights corporate finance professionals need to know to keep up with their constantly evolving industry.