Wiselike Question: Lessons Learned What are some lessons learned during your transition from a startup to Fortune 40?

This was a tough question to answer in a short-form context. I am sure I am missing massive details you are looking for, specifics you are craving and situations and people that I can point to for reference. It is the reason that I started to actually write this all down to hopefully, someday publish a book about my experiences.

Transitioning from running starts-ups and working with larger corporations to actually working for and inside a Fortune 40 like Target was an enlightening experience. To say there were lessons would be an understatement, to me it was more of an education in business: listening, learning, teaching, understanding, politics and strategy that I think would be difficult to impossible to find in higher education. The journey for me was fortunate, as I was able to come into Target with the help and support of senior executive leaders to help drive a transformative change in their digital products – not having to work my way up through the ranks.

In the first days, I was positioned as a consultant and thought leader for helping shape product ideas into minimum viable products (MVP’s) and focus on user experiences to help teams understand the way a startup would look at solutions to problems that their guests were facing. What happened next was a sea change within the teams I was a part of, even up to the executives that were sponsoring my efforts. People were realizing there was a better, refreshing way to test, iterate and deliver solutions that was so outside of what they were working on that it made their jobs exciting again.

This excitement became quite contagious, however there were some downsides because of the size of the company and how quickly things were now moving with the products I was helping. Many people that weren’t close to the work didn’t understand it, questioned the decisions and planning and more importantly felt it was dangerous for the enterprise and its established practices. Although I know now that I could have done a much better job at communicating what was happening and why, I still didn’t understand some of the hesitation and flat out resistance I was running into because I have never felt or seen that before at a start up. With a small team fighting to stay alive, attacking issues that they hinge their future on, a start up can’t waste time with politics, over-communication or long-term roadmaps. For an enterprise, things can get territorial quickly and “ownership” or “decision rights” can become a weapon against change that is needed to transform processes and deliverables for the future. When Cartwheel was in its infancy, there were massive amounts of territorial issues, from the C-Level suite down to the partner teams that we worked with internally. We lost budgets, conference rooms and even support because we started to challenge the basic structures and jobs of many. Before it got really ugly, we were able to work closely with senior leaders to make sure they understood why things were seemingly going south. The scrappy behavior and lean nature that I was used to and what I was teaching helped us through this period.

It took weeks and a well composed PowerPoint deck to show these leaders and teams what we were up to, why we were moving fast, why we weren’t doing things “like we always do”. Slowly the support returned and we were able to really drive change and the product. During this time, I shielded many of the product teams away from this internal fight because I felt things could quickly get personal since many came from the teams that were part of the challenges.

When Cartwheel initially launched, the press and attention was something I wasn’t used to. For a startup to get a few mentions in the press or even on the front page of TechCrunch, you either have to make some waves or know someone. On launch day we had over 100 media outlets cover us and luckily, most were positive. What that did for the moral of the team and the work we were doing was paramount to people understanding what we were actually working on in a sequestered conference room with a lock on the door. The problem however was that many internally wanted to use the model without understanding it. The term “Cartwheel it” quickly became the nomenclature used to describe how we were going to do the next project or fix what might have not been going well. It spread faster than I thought anything could within a company; the next step was to obviously address that.

My position started to shift into more of a communicator, presenter and educator on what things were working in Cartwheel and how that would be used across the company. I also started mentoring a few other product leaders to “take over” after I was going to end my consulting arrangement. I am a very action / goal orientated leader. I have been described as a “war time” general that needs a mission, a mission that will get done. The communication, socialization and work that was needed to instill change was difficult because I wasn’t directly leading the teams that I was teaching – I couldn’t instruct them to take the hill I could only show them the map. This actually became the largest lesson of them all, I am at my best when large-scale change is needed, direct and attainable goals are set and a clear strategy can be communicated out to teams to run after; pretty much exactly how a start up founder needs to operate. Over a few months, that work turned into more of the future planning and strategy of what was possible across the digital products of the company and ultimately into the first VP of Product job to make it all happen. I had a hill to take and it was a big one.

When the job became official, things changed even more. There was a mutual respect from peers, a greater ability to push change with teams and access to even more of the company and its resources that were needed. The downside was that I was now part of a much larger organization, I had direct reports (16 to be exact), and a boss with a boss and so much process around that it was daunting. I traditionally focus my work on my team and product(s) about 80% of my time, reserving the remaining 20% for other management needs. What happened was the flip side of that ratio – I was swarmed with committee meetings, reviews, and weekly statuses with my direct reports and more that just ate up my time. I did my best to change what I could, to instill a true agile mindset with stand-up meetings, working sessions to help. Although I was able to still drive the overall strategy and work that was needed to define the future of Target.com and the mobile applications, the application strategy for the company and how we needed to change our architecture and infrastructure for that strategy, most of that work had to be done away from the teams and after hours. My schedule didn’t allow any other possibility. Add in the fact that I was only on-site with the teams every other week and the problem was compounded.

At the end of the day, I learned more than I could possibly imagine from my team, my product managers, my peers and my leaders. I was able to work with some of the smartest people I have ever worked with, people with the experience that I have been striving for all my life and I soaked it all in. Being a founder, you try to build teams around you that are better at what you do to create a great company. I was able to slip into one of the best companies in the US and learn from true leaders. From Jason Goldberger, my immediate boss, to Casey Carl, Jeff Jones, Laysha Ward, Todd Waterbury and even Brian Cornell – I watched how they worked, navigated complex political situations and ultimately took the action needed to drive the company forward. I worked and learned from hundreds of the best and brightest, some that left while I was there, some that are still there and some that will run companies themselves one day. I consider them my professors of business, in the school of the enterprise.

If you use today’s successful startup descriptions for what I was able to accomplish; I created a unicorn-level mobile application and was responsible for several multi-billion dollar products – not something you can really pull off with a startup in a short amount of time. I think the ultimate lesson here is that when I have the resources, capital and room that an enterprise can provide I can create what I have always wanted to create in the startups that I founded, massively successful products built by amazing teams.

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