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What I’ve learned as a CEO working for a CIO

I’ve spent most of my career as a CEO and entrepreneur.  I founded, built and ran as CEO a $40M/year venture-backed digital media company for 9 years, from the time I was 27 until I was 36.  In the 5 years since, I’ve been an SVP of a $300M/year digital media company, briefly was CEO again of an eCommerce company, and for the last two years have been a VP at a Fortune 250 company.   But in my heart, no matter what my title, I’ve never stopped thinking, and trying to act, like a CEO/entrepreneur.

In my current role as VP/GM of a business unit, I work for the CIO.  That’s pretty unusual – for a business unit GM to report into the CIO.  But this isn’t your ordinary CIO or situation.  We worked together previously as colleagues; where I was SVP and he was SVP/CIO.  We realized then that we shared the same view towards innovation and strategy, and the same passion and approach towards leadership.  We agreed back then that we wanted to work together for quite a while, and either of us would work for the other, it didn’t matter.  When he left that company to become the youngest C-level executive of a Fortune 500 company, he was the one that suggested to our current company that we create a digital business unit under his leadership, and then he recruited me in to lead that unit.  He would be my boss and partner, not in his role as CIO per se, but as a senior leader of the company.

But his “day job” is still as CIO, and much of the way he approaches his work is shaped by his years of working his way up through the technology ranks at various publicly traded Silicon Valley tech companies.  CEOs and CIOs approach their work very differently, and I’ve become a better “CEO” by letting my CIO boss rub off on me.

A CIO runs a function, not a business unit.  A CIO must understand the latest in technology trends, be able to build products on time and on budget, scale up economically to support the needs of the business, problem-solve how to build new solutions in a world where he/she has inherited a number of legacy systems, and be able to hire tech talent in labor markets where such talent is almost always in high demand.  A good CIO will develop a mental framework around “optimizing” for scale, whether that be through organizational design, where to place talent, and how to best support the business’ needs and priorities.  Especially at a multi-billion dollar, multi-national Fortune 250 company, the CIO has to do all of this at a scale and pace, and under a level of scrutiny and pressure, that is nothing short of world class.

By contrast, a CEO builds and runs an entire business.  Generally a good CEO is focused on articulating a vision, and inspiring a leadership team (and the entire company) to accomplish that vision.  A CEO usually is good at viscerally understanding how their vision should be experienced by the customer and seen by the world, and how it is differentiated from the current landscape and the competition’s offerings.  Vision, passion, leadership, and tenacity are the skills and mental framework for the effective CEO.

Rarely does a CEO get the chance to work for a CIO.  Something interesting happened to me when I did.  I was forced to learn new skill sets; not in lieu of those that I developed or brought to the table as CEO, but in addition to those skills.  And I feel that it has made me a much better “CEO”.  Now, when thinking of how to build an organization or bring a product to market, there are new “synapses” firing in my brain that never used to be there.  I start thinking right from the get-go about the market landscape, speed to market, scale and organizational roles around building and supporting that product in a way that just wouldn’t have entered my mind so early in the visioning process.

And, surprisingly, the initial vision and passion I bring to the table as “CEO” for these initiatives doesn’t get watered down by adding this “CIO-like” framework to the equation.  In fact, it’s the opposite.  Now, built into my vision for an innovative product, platform or customer experience, I am more apt to layer into that vision a point of view around how to implement, scale and maintain a competitive differentiation.  Usually CEOs have to confront these realities around implementation and scale a bit down the road after they have used their sheer passion, vision and leadership to get investors and employees to invest money, time and effort in their initial vision.  And many would say that if the CEO wasn’t a little “naïve”, the original idea may never have been presented quite as passionately.  Many times that’s true.  But after working for a CIO for two years, I’m here to tell you that when you can combine the CEO-like raw vision and passion with CIO-like detailed planning around implementation, scale and design, it’s a much more powerful initial vision and one that’s even more likely to succeed.  I know it has forever improved my abilities going forward.


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