The Hocus Pocus of Virtualization: Reflections on 9 years of IT Sales

Shortly after my head hitting the pillow one spring evening in 2011, I fell into a dream where I was in a new construction neighborhood, looking at homes. I made my way into the subdivision’s model home, and found myself in front of the builder himself. After a few seconds of describing his workmanship, and providing some construction detail, he begin to go on about how one of his floor plans had two other houses inside of it. Looking at him with a brow raised, I grinned and chuckled; no such thing of course, 2 houses inside another. But he insisted, saying that was his Standard plan, and what’s more, he had an Enterprise plan, that had 4 houses inside of it. My chuckle turned to incredulity at this point, as I let the builder know that I had a background in construction and that despite his despite his best efforts, he wasn’t going to sell me on this nonsense. But he didn’t stop there! No, no, better yet, he had a Datacenter plan at the end of the street that allowed him to build as many houses inside of it that he wanted! What. The. Heck. Tired of this guy’s routine, I told him to have a nice day, and made my way out.

It was right at this point where I woke, nearly laughing out loud at the absurdity of it all! I was a fairly new Microsoft Licensing Specialist at Dell, and just swimming in Microsoft technology. I was treading water of Windows Server, Hyper-V, SharePoint, Lync, System Center, Enterprise Agreements, Select Plus, all other things Microsoft related, and they were beginning to manifest themselves even in my sleep!

Flash back to somewhere around 2008, less than a full year into being a software & peripherals rep at Dell, and I found myself in a team meeting with my manager, and a product specialist he had brought in to tell us about this new solution we were going to start selling, called VMware. I sat in disbelief as this specialist told us how the technology allowed something called ‘virtual machines’ run on top of an existing operating system. Again, what the heck. I wasn’t sure if this guy realized the year was only 2008, not 2016, but no such thing was possible. Hocus pocus. No way was any of our customers going to believe this campfire tale, let alone give us actual money for it!

Well, flash forward to 2016, and wouldn’t you know, our company closes on one of the largest technology deals in the history of history, and VMware, with it’s so called ‘virtual machines,’ is a big piece of the equation. Talk about irony. Fortunately by this time, I had managed to master the Microsoft Licensing Specialist role, become a sales coach and sales leader who taught others those technologies, served as a Microsoft mentor to sales reps moving to the field as account executives, served as a reliable & trusted resource throughout our organization, driving strategy on licensing opportunities that eclipsed over $30M on a single deal at one point (even had our company consultant call me for advice, lol), ultimately all things Microsoft related, and then even became a Dell-Microsoft Account Executive myself; the biggest of all the ironies! And now I find myself mentoring with VMware resources, taking as many VMware courses as I can get my hands on from VMware direct, Linkedin, Skillsoft, anywhere, to keep my skill set crisp, and have a balanced perspective. I’d probably prefer not to have virtualization dreams, but at least at this stage, I can recognize it as a sign of good things to come.

But beyond the witchcraft of virtualization, Microsoft and VMware, my 9 years at Dell have been chalk full of lessons in sales, personal & professional relationships, work-life balance, corporate culture, entrepreneurship, and many others. These 9 years have gone by faster than I’d ever imagine; they’ve seen me accidentally IM a manger that I basically thought he was an idiot, work peer’s weekend shifts for cash, sell technologies I had no clue about (WAN optimization, srsly??), travel across the states, jump off a really tall building in Vegas, travel to Canada, see a Cubs game from the rooftops, met Dog the Bounty Hunter (!!!!), had customers tell me more intimate details about their life than I’d ever care to know, make lifelong friends, all in the name of Corporate America. I’ve determined that I’m going to begin a semi-regular original content cadence on Linkedin, covering some of these topics & stories, and preemptively using my own advise from a future post, ‘Linkedin & your company approved news article: how to look exactly like every other person and never offer your own perspective (3 likes though!).’ It’s something that I imagine will be therapeutic, help me re-learn the craft of writing (used to be a literature major, once upon a time), provide some chuckles even if only to myself, and perhaps get noticed by someone who will recognize their organization simply cannot run another day without my leadership. See, chuckles?

With all that said, check back in soon for my next post, ‘Corporate America & Work-Life Balance: the single parent’s nightmare.’ I’ll be detailing a precise plan that will allow single parents everywhere the ability to feel like they’re never fully accomplishing anything, always running late, always forgetting at least one thing, and never able to get a sitter for that evening event. Guaranteed to be a page-turner!

***I originally shared this story on Linkedin, on 12/13/2016. You can find my profile here: www.linkedin.com/in/matthewcourtwright

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