View from the Top: CFO-turned-CEO Shares His Wisdom

Errol Olsen leverages years of experience as a finance chief to gain an edge in his new, higher role.
Errol OlsenMarch 10, 2014

The past few months have been a bit of a whirlwind. Three years in as CFO at a publicly traded company, Absolute Software, I was working hard, meeting with shareholders and financial analysts, and shepherding the growth that will take our company past the $100-million-mark.

Today – after some leadership changes – I find myself sitting in the CEO chair.

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It’s an interesting perspective and, admittedly, I’ve had to make some adjustments since my December appointment in order to focus on a broader view of the business.

My Top Three Takeaways
1. Financial insight.
As CFO, I had a broad view of the financial environment that provided unique insight to the business. Coming into the CEO role, I knew which

Picture of Errol Olsen

Olsen: Talking to people is the best part of being CEO.

product lines were healthy and which were operating at a loss, where we were growing quickly and where we’d stalled or rarely succeeded, and the current and potential profitability behind each initiative. I also spent a great deal of time with financial analysts and shareholders, so I had a solid understanding of what the market expected from the company as well.

Having all of that information as background and context has been a significant strategic advantage for me in my new role.

2. Decision-making. CEOs often focus on whether a decision makes good sense from a strategic or market perspective. However, as a CFO, the ability to drive a direct linkage to shareholder value was always in the back of my mind. That has allowed me to add an aspect of financial consideration within the CEO decision-making process. For example, acquiring market share does not lead to shareholder value unless there is a defined path to long-term profitability.

The flip side is trying not to be too financially focused, or too literal or numbers-driven about things. As a CEO, so much is subjective and intuitive, and that’s the part of my brain that I’ve enjoyed turning on. I’ve come to realize that not everything is binary. I’m learning to accept that and take some leaps of faith as well as make more decisions on an intuitive level.

3. Personal interactions. With the benefit of hindsight, I now realize that you become what people expect of you. As a CFO you adjust to fit the expectations of the role — that is, you are conservative and pragmatic. You are definitely not the marketing guy. You say no a lot, and others may perceive you as the bad guy when tough decisions need to be made.

Transitioning to CEO means expanding beyond that persona and being the person you really are. I love talking to people, but as the CFO I couldn’t do that a lot because I was stuck in front of a computer, cranking numbers. Even when I did talk to people, I’d be thinking about numbers. Now I can spend an entire day doing it. For me it’s the best part of being CEO, because every time I talk to someone I learn something.

If there was one thing I wish I’d done as a CFO to prepare me for this role, it would be spending more time with the sales force. A better understanding of what salespeople go through and the challenges encountered by our customers would be incredibly valuable.

CFO / CEO Relationships
From a CFO’s perspective.
Take the lesson from me and get out there building an understanding of not only what the trenches are like for the sales folks, but of all areas of the business. CEOs are involved across the entire organization, and if you want to understand their perspective and ultimately own the role in the future, that’s where you need to be. Pick up the phone, and travel to other offices. It will let you see eye to eye with the CEO and understand what’s driving his or her priority list.

From a CEO’s perspective. Remember that the CFO is not trying to be difficult but rather is acting a certain way because that’s the expectation of the role.

A majority of CFOs come through the public-accounting environment — they’re auditors, trained to find things that are wrong. It’s no surprise that they have a bias toward that versus finding things that are right. That bias is generally the biggest area of clash between a CEO and a CFO. Also remember that CFOs bear more responsibility from a regulatory and legal perspective than anyone else in the organization. They’re expected to toe the line and ensure everyone else does the same. CEOs that keep this in mind and apply a little empathy may build a more positive and productive relationship with their CFOs.

What Hasn’t Changed?
My Type A personality remains. I’ve been a risk taker all my life. Outside of work I regularly ski double-black runs and mountain bike on extremely rough terrain, and I’ve had some pretty wild surfing adventures. But I tended to cover that up in my CFO persona, instead being the one to provide sober second thought to the exuberance of the CEO.

Today I can leverage this part of my personality more so than when I was CFO. I’m making decisions that are larger in scope. And although I would never take unnecessary risks with the business (my background as a CFO would never permit this), the ability to quickly assess and consider in the moment will definitely serve me well in the role of CEO.

Errol Olsen is the CEO of Absolute Software, a provider of technology and services for the management and security of desktop and mobile devices. He joined the company in 2011 as CFO, before which he ran finance for two other software companies. He continues to keep a close eye on financial matters, overseeing Absolute’s director of finance.