Consulting Track to Fortune 500 Chief Strategy Officer

From Dartmouth to I-banking to law school to law firm to consulting (BCG) to Dollar Tree… certainly not the most direct route to becoming Chief Strategy Officer of the 111th largest company in the country, but here I am.

When I joined Dollar Tree 15 years ago, we had one business and 3,200 stores. Now, we have over 15,000 stores across two banners (Dollar Tree and Family Dollar) in two countries (US and Canada) and approximately $26B in sales. I’m responsible for strategy and vision and the key initiatives each year to achieve the vision. I’ve also headed up digital for the last two years, which covers omni-channel, e-commerce and digital marketing. I also drive many business development and consumer research opportunities.

Describing my “day in the life” is hard. One of the cool things about my job and team is that it is NOT repetitive. In a given day, week or month, the initiatives we are working on touch every single aspect of the company – from store operations to merchandise to real estate to supply chain etc. And we work on many different types of work and analysis. On any given day we could be in stores talking to associates or customers, diving deep into complex analytics, assessing competition or finding new growth avenues. And of course, there are always ad hoc items from the CEO or executive team.

My work is like an internal consulting firm but not detached from the decision – I work here! It’s great feeling ownership for the performance of the company and the results of our projects. We also implement and track to make it better. It’s the implementation where much of the value is created.

Another part of the “day in the life” is Digital. When I “adopted” the digital business, I ran the group directly, rolling up my sleeves and trying to figure out where we needed to go and what kind of leader we needed to run it on an everyday basis. I now have a strong SVP running the team. We use digital to support Family Dollar marketing and Dollar Tree marketing as well as drive sales, and I spend lots of time with this emerging group.

So how did I get here? Most people don’t leave consulting when I did – just two years after making partner. But I had an itch to become part of a management team and with long hours and being out of town most every week (and two young daughters), I found myself ready for a change. Standing in a parking lot in Maine one February and my wife called with the latest milestone I just missed with our 1-year-old pushed me over the edge. Did I want to see so much of clients or see my kids grow up? And on the professional side, I wanted to be more than an advisor. I wanted to help a company as an owner from the inside.

After nine years at BCG I let them know I was looking – it happens a lot. I started networking with other BCG clients who need strategy. A headhunter actually called one of my friends, and they connected me. That’s how it happened.

My time at BCG was excellent experience and the time at Dollar Tree has been amazing as well.

Advice? Life is too short to not love what you are doing. You need to talk to a lot of people and ask meaningful questions to get a real sense of the job. But also you need to be willing to make a change if you aren’t happy.  I also strongly recommend being selective. Too many of my friends have jumped at opportunities that were only ok in order to run away from a jump that they didn’t like rather than towards something that they might love and, not surprisingly, they didn’t last.