That Time I Accidentally Became the CIO

This my friends is a story of terror, trauma and technology. Read at your own risk. I will not be held responsible for nightmares. You have been warned.

In the later part of 2018, our long-time head of IT made the tough decision to move on to a new adventure. While we were thrilled for him and for his family, reality soon set in…until we figured out how we wanted to manage our IT needs, someone needed to step into the breech.

That someone was me.

Having written numerous reports and papers on the criticality of the CMO-CIO dynamic, the irony of being thrown into the day-to-day of an IT operation, albeit one within a small business, was not lost on me. I was prepared to have to race up a learning curve. I was even prepared to take advantage of the opportunity and see if new areas of innovation and transformation that I so often advocate for and sometimes tear to shreds were a path we should be taking. I wasn’t prepared for the totally un-sexy, not even close to transformative grind that the world of IT operations had in store for me.

What has it been like? Let’s start with the sheer complexity of stacks, sites and servers that needed to be mapped and understood. When you have had one person building your house for 15 years, it is understandable that he knew every inch, inside and out. But when he goes…so goes all that knowledge and wisdom. From cataloging service subscriptions to uncovering sites developed some 14 years ago aging on a long-forgotten server under the stairs (not kidding), it was astounding to dive into everything from URL management and email accounts to server and device details.

For those of you who know me personally, you can attest that I "might" be considered a fairly "type-A personality" – I like order and have a certain definition of what order means to me. (Your honor, for the record, I said MIGHT BE...) Nothing about our IT operations fell into my definition of order.

Job number one was bringing some order to a land of chaos. I needed tabs…legacy, new and future…just to even wrap my head around our stack let alone start to outline where that stack should and could evolve. I needed inventories, lists and spreadsheets…lots and lots of spreadsheets. I also needed policies that were updated and not hanging out somewhere in 2004 wondering how we should manage a Palm Pilot to connected to our systems.

Oh…and I still needed to do my full-time marketing job.

Then there were the “help desk” calls. OH, MY LORD the help calls. I have heard more people offer to “google options” if I “can’t figure it out” as if visiting Google for IT support is as wise as visiting WebMD for a medical diagnosis. I have spent more time unravelling “Googled best intentions” when the original solution would have taken 5 minutes to resolve.

The absolute WORST part of this new gig HAS to be the sales/marketing emails and calls…every one of them sounding exactly like the last and filled with the dire warnings of dark days, cataclysm and catastrophe. From stern warnings security to the crippling doom of failing to embrace AI and Blockchain to manage the massive influx of data and rabid prosecution of regulatory misdeeds, every pitch had one message: Adopt or DIE a MISERABLE, PAINFUL DEATH.

To be sure, this was a stark lesson in fear and loathing in the state of marketing. It was clear that everyone from security solutions to device management platforms had opted for the “without us you will be a sad, lonely, broken wreck of a business” narrative.

The warning-as-messaging content was probably most clear when a martech solution was being sold to the IT team. While some highlighted why marketing would love the platform because it was so simple to use even a child could utilize it…the message to IT was always “Don’t worry, we got your back when those moron marketers start to mess everything up.” One company’s marketing strategy was to literally pit marketing and IT teams against each other.

• To IT: Use AI to eliminate the burden of making sure Marketing doesn’t incorrectly use data and bring on fines and lawsuits.
• To Marketing: Use AI to identify new and exciting ways to use data without worry and without IT refusing to help.

Same Product! TRUE. STORY.

There was another yarn artfully woven into the messaging: Dear IT, we get how under-appreciated and unloved you are…so bring it on in buddy…let us give you an ego-boosting hug because YOU are awesome and THEY will be dead soon thanks to the aforementioned burning inferno of doom heading the company’s way. This…THIS is where I actually felt most embarrassed by the marketing messaging my own tribe had unwittingly unleashed upon me.

Thanks to this adventure, I have learned a new truth about the world of IT: the job can 100% completely and totally SUCK and nobody seems to worry that the people who bravely FILL these IT roles don’t deserve a single bit of it. It is a minefield of active ordinance just waiting to be set off by one incorrect password input or one misplaced cell phone.

As I have started to push away from my accidental foray into IT  and we start to establish a “team” of internal, cloud and managed services to assist, I also have new questions to ask of each of those new resources, team members and partners that I hope are more intelligent than what I would have asked before.

I want strategic answers to HOW: How can we achieve our business goals not how can they fix an immediate mess that I likely had a hand in making. How are we looking at the stack as an enabler instead of how are we managing the cost of technology. How are we drinking our own champagne and actually utilizing the tools at our disposal instead of how can we buy the next cool toy. I need to commit to a more elevated conversation if I expect elevated strategic help!

I will ALWAYS need IT “help” as a function of being a connected, tech and internet dependent executive. But I hope to be far more connected to the opportunities and roadmaps IT sees ahead of our business than the train wreck of help tickets our operations can leave in its wake. I can only hope that this commitment to IT as partner not peon is adopted by those of us messaging to both marketing and IT leaders.

It doesn’t help the ecosystem when a sales pitch raises flags around what one team may or may not do or how fast the business will burn to the ground without a specific solution. What is helpful is being the voice of innovation and reason that helps ensure that all boats rise with the IT and Marketing tide.