You won’t believe what happened next… A new chapter in my career that I almost missed

To say the last three years were life-changing, stressful and incredibly difficult would be the understatement of the century. In late 2012, when I exited my startup to find something new, I was burnt out and tired. I just invested everything I had, from money to time to focus for 6 straight years. I needed some time off and something different to focus on. The problem is, I didn’t have much time and I didn’t know what I wanted to do next. Those two things don’t work well together, especially in the mind of a recovering serial entrepreneur like myself. Within weeks I was worried, driving my wife insane and diverting my personal attention to projects that lingered from my inability to concentrate on anything else before. I didn’t do what I should have done, refocus and meditate on what I wanted, set the goals to get me there and then get to it.

About a month later, I received an email that was about to change everything. A client contact from Target wanted my help. If you have followed me for the past couple of years, you know what happened next. I went into Target, helped them build a product organization, launched Cartwheel, relaunched all their mobile applications and rebuilt from the ground up into a fully adaptive platform. I then left in August of 2015. That time taught me more about myself, what I wanted to do and more importantly, how I wanted to do it than anything I have ever experienced. It was a personal, professional and business school all wrapped into a grueling quest to make my mark on an enterprise. It wasn’t, however, personally fulfilling. I was spending massive amounts of time away from my family and the work began to get bogged down with issues out of my control. When I made the decision to leave, I knew what I had to do next. Absolutely nothing.

And so, for the last several months, I did exactly that… I did take calls, read emails, do phone consultations and talked to everyone I could to see what was out there. I made sure that everyone knew that I wasn’t specifically looking, but was leaving my options open, spending needed time with my family and focusing on figuring out what the best next step is. A trusted advisor of mine, someone that I hope I could even call a mentor, gave me some of the best career advice I have ever received – “if you act like you don’t need a job, you will get offers for all of them”.  Although I couldn’t believe it at the time, she was right. The truth of the matter is, I planned to take a year off, making sure I had some income and some savings to pull it off without causing too much pain and suffering for my family. What I found from that is a freedom and flexibility that I never really had before and it has resulted into an exciting next step. One that, interestingly enough, I almost passed up.

Now I wasn’t ever in a position where I was looking at a ton of offers on my desk like a unicorn startup looking at term sheets, but I was very far along with several companies, several times, looking at the specific brands, cultures, locations and impact that I could have on their operations and that they would have on my life and family. I was able to build up quite a check-list of what we wanted and didn’t want, what we needed and most importantly, what we didn’t. I brought my wife and daughter into every potential step and decision, making sure that we all felt the same, were comfortable with things moving forward and that we would be proud to talk about where I landed. Was I overthinking it? Probably, but I can honestly tell you that it really helped. I didn’t want to repeat the mistakes I made with startups, and I really didn’t want to repeat the issues I created with my work and travel for Target.

One of the largest issues for us is location. We love Portland. It’s home and we have built an amazing network here, both professionally and personally. It was the top check box on our list – we didn’t want to move. Unfortunately, for my career, that meant trying to find a VP or better job with a handful of companies that are based there. I spoke to the usual suspects (there are only a few enterprise level companies there) and others on a potential fit and role only to either find out that it was a culture I didn’t want to work in or a position wasn’t available. I was offered several executive gigs with startups that were very intriguing, but would require significant time for me to invest and honestly, I am not sure I want to do that again. So, we started looking around at roles and opportunities elsewhere. There was a Global Head of Product role in Massachusettes and a similar one in San Francisco that I explored only to turn both down. There was a CTO of Innovation in Texas that looked promising enough to fly down to Austin with my family for a week to investigate. Long story short, we hated Austin. There was an amazing opportunity to build a company backed by a massive hedge fund in Europe, with the ability to live in some pretty cool cities like Amsterdam. Since I’m a dual citizen, with both a US and EU passport, it was also a real possibility. The idea of living abroad was exciting, especially because my daughter was young and not in school yet. We felt that she would also benefit from being exposed to more cultures and languages so we planned a “living” European vacation, checking out a few cities – especially Amsterdam. Long story short, we loved Amsterdam (and will live there someday) but the travel was tough, being away from Portland with what we have there would have been nearly impossible and ultimately, the position wouldn’t allow us the financial freedom to keep our life going in two countries.

All in all, I spoke to over 10 different companies where I got deep into the process. My wife jokingly commented that I was the busiest unemployed person she’s ever seen. Somewhere in the middle of this exploration, I received an email from a recruiter that sounded interesting but didn’t check off a bulk of the items on our list so I simply replied with a “not interested, relocation isn’t an option at this time” and moved on.

Who would have thought that a month later, I would be thanking that same recruiter. What I didn’t know at the time was that this particular company was open to location strategies and that they knew what I did at Target and were specifically looking for someone to build out their new product organization. When I started to dig into the company, who I would be working for, and the opportunity to build teams in a field that I have been living and breathing for years (eCommerce / Retail) it started to look like a good fit. I then spoke to the company directly, first to my new boss and then to a few of my potential peers. Not only did I like each and every part of the conversations, each person embodied an energy and excitement that was familiar to me. It was entrepreneurial, it was the spark behind someone’s voice and eyes when they know there is a long and arduous journey for a treasure ahead of them, but they can see the destination and how to get there before anyone else. They were also, happy. This was by far the most peculiar thing that I noticed and it caught me off guard. It wasn’t because they were happy, it was because they made me realize that practically everyone else I spoke to at other companies wasn’t’. They also seemed to move fast, something I innately appreciate.

I jumped on a plane the day before Thanksgiving to Vancouver BC to meet the team in person, interview and get a feel for the place. Now my wife and I have been to Vancouver before and loved it, so the location issue wouldn’t have been a big deal if we had to move, but that wasn’t even an issue – this position that I was discussing would be based in Portland. Within minutes of walking in the door to their headquarters, I could feel the energy I heard on the phone, the company culture was palpable and ever-present. It was also contagious. That night, I was back on a plane thinking that I might have found the perfect fit. Speaking to my wife, we both talked through scenarios and plans of what it would look like, the usual Q&A that we were now used to, only to dismiss the finer details because we were under the assumption that we wouldn’t hear from them until after the holidays. The next day was Thanksgiving, and it was one of the first times in my immediate history that I wasn’t in a war room watching monitors and real-time sales data.

What we didn’t expect was the call on the next day, offering me the position of Vice President of Product for all their digital properties including what was fairly elusive for me at Target – in-store digital. This somewhat difficult but important piece was vital for me because I believe that the future of retail is the convergence of digital and physical, unified by a mobile device (you can see this message in my keynotes for MobCon in 2015 and more recently, my keynote at the Nordic eCommerce Summit). All the parts were there. A boss that I respected and admired and had the same traits that I valued in my boss at Target (someone who I will probably remain friends with for many years). The right domain of expertise where I was comfortable. A brand that is respected and a product that leads an industry. A culture that respects the work/life balance, mindfulness, happiness and health of their employees and backs it up with action. Finally, the ability to build teams where the talent is, including where I will be based, Portland Oregon. It even has the international appeal thrown in, completing the checklist and nice-to-haves.

Although I didn’t complete my year off, everything that led me to this role felt organic and has sparked my desire to work again. In the last few weeks, I have already started sketching ideas and notes on what I want to do and how I think we can do it. I am looking forward to working with everyone there, building some of the best digital products in retail. I am even looking forward to learning yoga and getting in better shape.

Let’s build amazing together, Lululemon.
I’m proud to call myself your new Vice President of Guest Experience and Digital Product Management.


One comment

  • Congratulations Alan, a thoughtful process bears fruit.

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