I initially wrote this blog entry as I was winding down my time at WE. At the time, I started to reflect on my four-year journey there. Overall, it's been an incredible part of my career, where I got to meet and work with some wonderful people along the way. I also got to do and experience some amazing things as well.

The Role

As WE headed into its 20th anniversary, one of their donors, Lane Merrifield, encouraged WE to take a different approach to technology, which led to the role of the Chief Technology Officer at WE. As its first CTO, my job was to help scale the organization through technology. My initial job description included the creation of a new Technology Division. The job entailed determining the new organizational structure, processes, and rebuilding our entire technology infrastructure. The rebuild would range from how we support our internal staff globally to how would we create technology products to integrate with our myriad of partners globally.

While the job started as a role focusing on engineering, it quickly expanded to cover digital products as engineering was extremely dependent on how we would bring products to live. As part of the Executive Team, I was able to influence how we would operate as an organization and drive us to become more customer-driven.

The People

Without a doubt, the thing I will cherish most from my time with WE is the friendships I gained on this journey. Most of my strongest bonds have always been born from work. For most of my career, I spent the bulk of my waking moments at work and given the high intensity of roles and jobs I have always taken, which results in intense friendships.

Among the friendships I've much appreciated at WE, it's hard not to start with Russ McLeod. Russ is the person who hired me, and over time we developed a bond of friendship that transcended our jobs. There are many things I admire about Russ. Among them, Russ has a knack for operations, and he understands the need to drive decisions through numbers and discipline. The most substantial testament of his brilliance is represented in the Trips Division that he spearheaded for many years. His team is always the first to be willing to try out new ideas that might make them better and doesn't shy away from constructive feedback. The thing I loved most about Russ though, is that he is humble. He's always willing to be challenged even if he doesn't accept it at first glance (which in my mind, no one should). Russ also trusted me to make the changes and recommendations that I needed to drive the things I thought were essential to the organization. In my journey at WE, the one certainty I always held was that Russ cared about me and would have my back. Russ often describes me as one of his best friends at work. I describe Russ as my brother - someone I admire but can also disagree with like little kids.

I consider myself incredibly lucky to have been surrounded by a fantastic team. A large part of my journey started with an accidental meeting when I joined the team creating our WE Day app on the first week that I was there. Little did I know that meeting would form the foundation of my journey going forward. In that meeting, I met three people - Ok Ikejiani, Hugh Nettar and Sonja Marcan - who would enable me to drive my strategy for the Technology Division. Jero Sutlovic joined us from Kinetic Café, a place I had previously worked, and Dan Kuzmicki, a WE veteran of 13 years, to ground the team on the history and culture of WE. Along the way, Emily Keane joined us to round out the core team. With this team, we would help transform WE to become a more customer-focused and business-driven organization. We were able to introduce methodologies like Agile Delivery and Design Thinking and introduce the idea of Digital Product Management as a discipline to bring this to life. I'm not only immensely proud of this team but also one that I've truly learned to care about.

The testament of the team can be seen in this photo as you have members of my full leadership team from the past and present. I took this photo at my home at Christmas. This photo comprises of members of the team that have left the organization as well as people who were travelling at the time. They were dialling it remotely to be part of the festivities.

Heather Harkness has been my very best friend and peer. With Heather, I found a friend who I could partner to move the organization forward strategically. Heather and I spent many hours in front of whiteboards designing the future of WE together. There were also many hours of laughter and some tears along the way. We always confided in one another, and I could always count on Heather to have my back no matter what.

The biggest differentiators for me are the co-founders and the executive team. I have always put together strong teams and found a group of peers whom I could count on. However, this is the first time I've worked with co-founders which are brilliant and kind. Marc, Roxanne and Craig spend a lot of time figuring out what is the most compassionate course of action the organization can take without jeopardizing its mission and its fiscal responsibilities.

The Struggles

The core of WE's struggle is that it is a 25-year-old organization traditionally staffed by young and inexperienced staff. As a result, the organization has grown very organically and has incurred operational debt as most organizations would along the journey. However, this is something that the organization has recognized and has been actively remediating for a few years. They continue to bring on more seasoned staff to mentor talented young teams while starting to invest in paying down some of their operational debt along the way. As an experienced professional veteran, it is easy to recognize that the operational debt incurred is on par for the organization of its age. However, given that the staff has traditionally been quite young, this often causes much angst and sometimes unrealistic assumptions of how fast change can occur given the size and age of the organization.

Reflections

The journey at WE is something that I truly cherished. It has been a fantastic journey here at WE. I got to meet some incredible people who have become friends and family. I was allowed to do some tremendous things to drive change for the organization. WE is not without its flaws, but despite the shortcomings, it is an organization that has both the desire and willingness to continue to improve itself. It's been three months since I left WE and I still miss my team and the people I worked with.

While I am sad to go, I believe that I have left WE in a better place. As I begin the next section of my professional journey, I'm excited to be starting a new journey at ThoughtWorks.