Winners Fail, Losers Hide.

A Reflection on my Time in the WWT Associate Academy

I spent the last week in St Louis at WWT GHQ with Cohorts 6 and 7 celebrating our graduations from the Associate Academy and it was such an incredible experience. It's led to much reflection within me on the academy, and how special it, and WWT, are as a whole. To best paint the storm of emotions currently crackling within the walls of my brain I feel it best to start at the beginning. Well, – not the complete beginning, let's start at the widely accepted beginning of adult life. I graduated from college and moved to Austin to start at an OEM, who is now one of WWT's largest partners. Within their sales academy, they built a strong foundation for us as sales professionals in the IT industry. We were quickly brought up to speed on the sales process, best practices in call structure, the basics of IT infrastructure, and the past, present, and future of technology. It was a great framework to pair my passion for technology with an inside look at the industry, what professionals were experiencing, and how to pair them with technologies that enabled the achievement of their goals.   

Life famously has a pattern of not going the way we plan, fast forward a few years and I found myself in Seattle. I started at WWT this spring, and had a great foundation for the industry but found some pretty significant gaps in my understanding of what WWT was capable of. Sure, I understood the technology, but hearing the stories being told of the innovation and capabilities World Wide is famous for made it clear I needed more. In order for me to best speak to the challenges my customers were experiencing, I needed something to pair my industry knowledge with the tribal knowledge and value propositions we were best at to best tailor it to my customers.   

That's where I found the WWT Associate Academy, or more accurately, where they found me.  

From the onset Cohort 7 was to be a unique type of cohort, one that would be accelerated to a 12-week timeline giving us a crash course on WWT, our capabilities, industry certifications around the technology, and some sales framework to help us quickly mesh with the account teams we'd be joining in the very near future.  

All at different points in our careers, different backgrounds and specializations, the person on my left took an entirely different path to the academy than I did, both entirely different paths than the person on my right, and so on.  

How could we balance this dynamic? Would social norms and cultural differences affect our ability to build relationships, band together, and learn quickly? Fitting in, nonchalance, and uniformity dominate culture today, would we have the courage to see our differences as strengths and have confidence to mess up? Or shrink, stay quiet, and make the "safe" decision to not take risks and mirror yourself to fit everyone's expectations.  

Starting Over

When I was a kid, I wanted to learn how to play an instrument. 4th grade rolled around and we got to go around to the orchestra, band, and choir classes to try everything out and pick which one we liked best. I chose viola! I liked the way it sounded, that it was comedically larger than the violin my best friend chose, and I quickly became obsessed with the soothing low, dark, mysterious notes that escaped it as I waxed and waned across its strings.    

Again, life doesn't always go as we plan! A family move from Colorado to Kansas meant a new city, a new school, new friends, and most importantly: a new orchestra teacher. The idea of starting over or proving myself candidly was not a fear entering that new school or classroom, I like people! The things that excited me about the world as a 5th grader like traveling new places, meeting new faces, and seeing what motivates and excites them are still things very near to who I am as an adult. 

There was, however, one problem I could've never foreseen. In Kansas, Orchestra classes started in 2nd grade. Which meant I, a lowly second year violist, would be forced to sit with the fellow second years. A classroom full of 3rd graders, children, and I, a 5th grader who had the world figured out. A borderline adult!  

So I made a perfectly reasonable decision for a 5th grader scared of being perceived negatively or childish by others. I quit orchestra. And joined choir with my similarly aged classmates.  

I think about that decision regularly to this day. I don't blame myself for it, nor do I wish I made the opposite decision. Choir ended up working out quite nicely for me, I made State choir in high school and presently serve on the board of a community choir in my neighborhood in Seattle. But the decision to not learn or do something solely because of fear of perception of others is one I hope to never make again.

Which brings me to the most meaningful part of the WWT Associate Academy.  

My favorite part of the academy (other than fellow cohort members giving me funny words to slip unnoticed into my corporate overview presentation each week) has been the people and the wide breadth of personalities within our ranks. We're all at different ages, different points in careers, working shoulder-to-shoulder, learning about technology and the story of World Wide. 

Everyone in my cohort (and Cohort 6, I'll claim them too) is a BEAST at something. Whether it be partner knowledge, organizational skills from a project management role, a deep understanding of the technology, or a first hand experience working in the NAIC and ATC and a mastery explaining it others -- each person in my cohort had something vital to our team's success to bring to the table. 

The final capstone of the associate academy is a mock Account Planning Session. You get randomly assigned teammates and try and to implement everything you've learned in the academy in one big project. Researching a customer, assessing their business, goals, and roadmap. How WWT can partner with specific OEMs to tell a story and meet a customer exactly where they are. It's the perfect stadium for a team full of unique experiences to mesh and create something meaningful, together. A presentation that feels like a classically orchestrated ballroom dance between each team member, each new section a tempo change with different corresponding moves and rhythyms.  

A Mantra Worth Stealing

There's been a reoccurring theme throughout Cohort 7's academy experience. It is often attributed to be a "Cooperism" of my own creation, but this feels like a good time to finally come clean regarding the origins of my favorite phrase. A couple of months ago, watching the press conference following Game 3 of the second round of the NBA playoffs, I heard something so profound it sent a chill through my bones.  

Winners fail, losers hide.  

My beloved Oklahoma City Thunder experienced some injury woes during the postseason, and it forced them to start Ajay Mitchell, a 23-year-old point guard in his second season from Belgium, freshly recovered from injury with almost zero playoff experience. He went 5-20 from the field, a paltry 25%, significantly lower than the league-average of just over 47%. It would be completely reasonable to be frustrated with your young player after a performance like that and yet, Thunder Head Coach Mark Daigneault did the exact opposite in his media availability immediately following the game.  

Mark complimented his ability to have confidence in what got him there, taking a career high 20 shots in such an important moment. He said that the coaching staff can help him develop as a player in the future, but they can't make him play quickly and decisively. They can't coach him into action. But they can show him his mistakes and advise him to learn from them in the future.  

Winners fail, losers hide.   

This is the goal of the associate academy! Sure, there were things that were more important than others, a presentation in front of management or a partner OEM, but the goal the entire time remained crystal clear. Jump in, try your hardest at something you may not fully understand, be a great teammate, and learn from doing. You might mess up, and that's okay! This is the time in the place to do it. There will be plenty of stressful customer-calls, high-leverage presentations or demos, and important manager 1x1's in all our futures that will certainly feel too important to mess up. Leave them in the future. Our goal throughout the entire academy was to soak up information, do our best to put ourselves out there and try new things implementing our new knowledge, and to mess up. A lot. So that the mistakes created a memory and a framework of best practices when presenting to a customer, working within a team, and simply being a good person.  

Winners fail, losers hide.   

Although my time in the academy has come to a close, it is not a chapter I soon will forget. The laughter throughout sessions with our facilitators. An unannounced forced computer reboot in the middle of a presentation. The "oops" and "my bad's" met with a small tweak and immediate progress forward.  

Sure, there was technology learned and books read and news dissected and presentations given and OEM's met, but the relationships created and the emphasis on having the confidence to try and mess up and try again, and on giving others the freedom to do that too, is what will stick with me the longest and what I hope to bring to my specific team in the future.  

There's always going to be someone older or smarter or more experienced in the room, have the confidence to do something outside of your comfort zone, make a mess, and start all over. The confidence to be the dumbest or oldest or weirdest person in the room.   

Matthew Whitaker, a TSA in Arizona with WWT said it best during a culture session in my second week in the academy  – 

That bounced around my head for a few months. Then I heard it again, differently and a little more concisely.  

Winners fail, losers hide.  

About the Author

Howdy! My name is Cooper. I joined WWT in February 2026 as an Associate Client Manager. I am based in Seattle, WA, but grew up as a Midwest kid in Topeka, KS. 

Professionally, my time as an Enterprise Account Manager at Dell EMC and Smartsheet sparked a passion for technology and for leveraging it to create unique solutions for the customers and companies I work with. 

Academically, I hold a bachelor's degree from Kansas State University, dual-majoring in Marketing and Professional Strategic Selling, with a minor in Spanish, and an emphasis and certificate in Data Analytics. My goal at WWT is to intertwine creativity with intentionality and to deliver unique insights and meaningful solutions to my clients and coworkers early and often.

Outside of work, you can find me playing rec basketball, singing in my local community choir, attending sporting events and finding live music every chance I get. I love any excuse to try a new restaurant, listening to an album front-to-back, and treasure time with my family and my friends.