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The Story of My Career – So Far...

I started in IT in the mid-late nineties. It was a crazy time in the industry. I’d answer the level one support line and the person on the phone would say something like, “I don’t care what you get paid, I’ll offer you twenty grand more and throw in a four thousand dollar signing bonus if you come work for me.” They didn’t know me from Adam – never saw my resume – but they didn’t even care. Of course, I’d always reply, “See you on Monday!”

So, I decided the best way to take advantage of this fat-rich environment was to start taking temp work. It could be anything from two weeks to six months – it didn’t really matter. There was far more work than talent available, so I could be as discerning as I wanted to be. I had just two non-negotiable requirements: it had to be something I’d never done before; and it had to pay at least $10,000 more than my previous assignment.

After several years of this, there wasn’t much in the WinTel and networking world I didn’t have some experience with. Those jobs I had not done, I at least knew enough about to manage others doing the work. This is when I started taking longer-term temp-to-perm roles and, eventually, full-time jobs. I wanted to get the experience of working in and managing larger projects and learning more about how businesses operate. I was also young, single, making great money, and trying to figure out what I wanted my life to be. I moved around the country a bit and tried my hand at many different things. So, I really saw even the full-time jobs as semi-permanent – at best.

In 2000, I found myself working at a tiny dot com startup. You could feel energy crackling in the air. We had fewer than fifty employees, and every one of us was expected to participate in every staff meeting. We were all not only expected to contribute our expertise and perspectives, we were actively encouraged to do so on every subject. We all genuinely felt that we were running the company together. This was the best job I’d ever had – so far…
I was on a first name basis with the CIO and the CEO. I’d sit and talk relationship woes with the CFO. The Chairman of the Board took it as a personal challenge to try and make me flinch, so he would throw punches at me in the hallway.

Pretty much everyone who lived through the dot com bubble, knew there was something else everyone could feel at the beginning of 2001. If you were inside the bubble and didn’t feel the foundations straining to hold up the weight of it all, you just weren’t allowing yourself to believe it. I knew the end was coming and the market would feel the pain of the collapse, so I looked for the most stable institution I could find. I wanted to beat the bubble’s pop and get myself onto a rock-solid foundation that would survive the coming market disruption.

I decided Citibank would be a safe place to spend a few years weathering the storm. As a bonus, that experience on my resume would serve as a life raft when I was ready to head back out into the market. When I did leave my Citi cloister and head back out into the open market, ELEVEN AND A HALF YEARS LATER, it would be with a career.

It would be impossible to overstate the culture shock that struck me when I went from the electric, startup environment to a company that had over three hundred thousand employees in over one hundred countries and an IT budget that would make dozens of national leaders blush. I went from being a critical engineer of a beautiful machine we were building together to feeling like a cog on a wheel in an insignificant mechanism of an impossibly large, complex locomotive – driven by an equally large man I would never meet.

But I learned. A lot!

Until Citi, I still had no career. I was in an endless string of jobs. There were some jobs I found extraordinarily rewarding. There were many jobs that were truly challenging and satisfying. Still, it was becoming increasingly clear that Jack-Of-All-Trades wasn’t a career I could hang my hat on in IT.

I didn’t remain an insignificant cog for terribly long. Citi is where I started to craft my successful (so far) career in IT Service Management, in general – and Knowledge Management, specifically. I was part of a relatively small team that would completely reorganize the structure of a business unit of over sixty thousand people, overhaul all the operations processes, and redefine Citi’s customer engagement model. We made a difference and people took notice.

People were taking notice of me in the industry as well. I was highly active in the burgeoning ITSM community of professionals. I had a fairly popular blog, a noticeable presence on Twitter, and was a frequent guest on industry podcasts.

It took me a few years to accomplish, but I finally drove my small team to convince executive leadership that we need a standing ITSM program office. After a few months, once my new Senior Director had his bearings, we discussed my future. He wanted me to use the Incident Management processes I built for the Americas as a model for a global rollout. He offered me a promotion to Senior Vice President, a big raise, a greatly expanded staff and a budget to meet my goals. He also said, “Or… You can do that Knowledge Management thing you’ve been riding me about for two years… You won’t get the promotion. No raise. No staff at all. And you’ll have to do it all with no budget. You’ll have to find stakeholders and convince them to fund your work.”

“I’ll take it!!” I started on the path of successfully convincing nineteen executive leaders to each fund a portion of my budget, while I searched for a vendor who could deliver what I was looking for. It took me several months to find a platform vendor who even understood what I was trying to accomplish – let alone deliver against my requirements.

When I found the right vendor, I flew out to Boston to have lunch with the CTO and tell him why the platform was the greatest breakthrough I’d seen in linguistic analysis, but their ITSM product was awful. He asked me to come work for him to show him how to do it right. At right around the same time, Citi was moving their operations center to Texas, so I was told to relocate or take an early retirement package.

I took the job at Attivio – as a contractor, to start – despite having zero experience in Product Management, because I believed in the platform and my vision for it. The risk seemed to be paying off. My redesign of the product earned me an ‘Innovation of the Year’ award from Pink Elephant, and I started working with vendors to build partnerships through embedding knowledge delivery components in their ITSM platforms.
However, as often happens with startups, there was a complete restructuring. They got rid of most of the leadership and asked me to return to contract work. By this point, I had moved across the country, bought a house and had twins. I needed the stability (and affordable medical insurance) of full-time work, so I took a drastic pay reduction to redesign and rebuild the internal IT Knowledge Management practice at EMC.

After about a year into that role, I’d heard about a position opening in EMC’s Services Division. They decided to redesign their entire customer engagement model, digital experience and internal operations processes – and the approach was to build it all with Knowledge Management at the core. It was an opportunity to play a leadership role, as the Senior Knowledge Architect of a small team building a truly knowledge-centered support model. I couldn’t pass it up.
As the Senior Knowledge Architect at EMC Services (and, eventually Dell EMC Services) I was given the opportunity to implement all I had learned, and apply all my theoretical approaches to using Natural Language Processing, Dynamic Profiling, taxonomical management through ontological integration, and so many other things, to bring about the convergence of Knowledge Management, Customer Service and Customer Experience Management. It was exactly the role I had been crafting my career toward.

Back around 2009, I decided I wanted to eventually be a “Director of Knowledge” – even though I’d never met anyone with that title. In fact, I’d never even heard of that role existing anywhere – but I decided it SHOULD exist, so I decided to make it my mission to convince someone, somewhere, to create such a role for me.

Every single professional decision I made from that point forward was with that astoundingly unlikely future role of Director of Knowledge as my North Star.

In the ten years since I set this goal for myself, I’d had six jobs across three companies. In that decade there had also been some tough decisions, rough paths, and challenging financial difficulties. Quite a few times over those years, I found myself wondering if it was a grave mistake for a high school dropout to turn down what would very likely be my only opportunity to land an extremely well-paid executive leadership role anywhere.

But I don’t believe in regret – and I didn’t have the tools or wherewithal to start over – so I just kept pushing. I didn’t really see myself having any other valid options, because I put all my professional eggs into this one makeshift – rapidly becoming threadbare – basket. I was also unwilling to relinquish hope, however, because four of the five jobs I had taken since making this decision were roles that were created specifically for me, or reimagined to match my unique skills, experience and perspectives. I took it upon myself to entirely redefine the fifth. I had no idea if my efforts would pay off the way I’d hoped, but it certainly felt like I was doing something right.

At the beginning of February 2019, I found a small (but stable and growing) company I could respect, who was looking to hire a “KCS Lead” to establish a new Knowledge Management practice in their Customer Success organization. The role, as written, was well below the stage I considered myself in my career, but I applied for it anyway. I didn’t apply because I wanted to take a step backward in my career – but because I wanted the opportunity to meet with the hiring manager.

I wanted to convince them they were wrong.

They had no Knowledge Management practices or infrastructure whatsoever in place yet. It was a truly greenfield environment. They thought they wanted a “KCS Lead” to start them down the Knowledge Management path. I wanted to convince them what they really needed was a Director of Knowledge.

After two and a half months of negotiation, I left Dell EMC and started as Zerto’s Director of Knowledge. (Technically, it was “Director of Knowledge Management” but I had plans to change that.)
What excited me the most was that the role, along with the entire Customer Service organization, reported to their VP of Customer Success. This was a structure I had been arguing for in the industry for years, and Zerto was the first company I found that understood the value of that.
This was my dream job!
There was simply no “up” for me from there. It was, quite literally, the pinnacle of my career. This was the last job I planned on having in my field, and I wanted it to be a crowning achievement I could be proud of. My next step was to bring my career to a graceful, painless end.
I absolutely love the career I’ve crafted for myself in Knowledge Management – but it’s not my vocation. It was time to decide what I wanted the next stage of my life to look like.

In my year at Zerto (before COVID-19 forced the staff reduction) I built and managed a bootstrap KCS practice, completely redesigned the internal customer support process for improved efficiency and augmented/automated knowledge capture, and led the design effort to migrate the organization to SalesForce Lightning.
I established and led a cross-functional Customer Success Council to align the end-to-end customer care processes across the enterprise.
I developed a plan to guide the enterprise from foundation laying to progressive implementation of a long-term vision of a redesigned customer digital journey. The roadmap included strategic use of linguistic analytics, unified search, simplified UI design, and other approaches, to allow Customer Success to scale with the growth of the enterprise.
I had spent a year laying all the groundwork, and the first solid foundational structures were set to be put in place at the end of April. I was laid off a month before I could see my plan put into action.

My work in this career is not done. I want the opportunity to build my legacy.

If you got this far, I truly appreciate you granting me this time from your day.

Regards,
Craig Wilkey

April 08, 2020, 05:16:46 am

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