Meet the Managing Director of our new Minneapolis office

August 22, 2019

Tom Wollan is a man on the move. After building a successful career at Best Buy corporate and taking on leadership roles at Amazon, Tom joined Stackline to help solve the hardest problems in modern retail. Now he's striking out on his next adventure as the Managing Director of Stackline's first expansion office, where he'll build a team that applies ingenuity and deep analytical skill to help accelerate the online growth of some of the world's most recognizable brands. The best part? This huge step for Stackline takes Tom back to his hometown of Minneapolis, Minnesota, where his high-octane career began...

What was your experience before Stackline?

My first role was in the buying group at Best Buy corporate in Minneapolis. I studied finance and operations in school, but I wasn't yet equipped to say, ‘You have to make all decisions based on data.’ I still felt that strong interpersonal relationships were the foundation of sound business decisions, and buying in the 2000s very much prioritized a mix of relationship-building and data analysis. It was a great first foray for me into the corporate world because I was able to flex both my quantitative and qualitative proclivities at once.

When my Best Buy director left for Amazon to take a similar merchandising role, I decided to make the same move. The message I heard from Amazon was that the approach to vendor management turned the traditional ratio of 80% relationship-building and 20% data analysis on its head. The role also included more operations and tool-building than traditional assortment management. We were responsible for optimizing our business across a handful of metrics, primarily by influencing decisions with data. The remaining part of the charter was essentially to find ways to work with vendor partners in positive ways. 

I moved through a bunch of different Amazon categories quickly, which gave me exposure to legacy categories, emerging categories, things that had automation, things that didn’t. But every step of the way I chose the next category based on the hard problem that team was working to solve. I wanted to lead teams solving hard problems. The last role I took as the leader of the footwear organization at Amazon presented the biggest challenge I had faced up to that point because everything was still bought via spreadsheets and emails -- very un-Amazonian. In other categories, we had tools that would tell a vendor how much to buy. But the apparel industry hadn’t evolved how manufacturers and retailers negotiated goods much beyond the process described in Shoe Dog. 

When I first stepped in as footwear category lead, I was still being asked to pay vendors nine months in advance for product, and there was no reprieve if my buys were wrong. We basically had to lead a process revolution in that category. We needed to make sound decisions based on data, and we needed to be protected if those decisions were wrong. When I joined that group, the mission was to get that 200-person organization buying through a machine and through logic. And the hard part there is that you had a lot of people on that team who liked traditional buying. We had to find a motivating, empowering way to communicate that we weren’t going to do it the same way anymore.

Through all of my Amazon experience, hard problems continually arose. And after a while, I realized that in corporate America, there are only so many fundamental problems to solve no matter how high up you go. That’s when I realized I needed to find my way to a smaller company where I would have an opportunity to test my ability to make something and really help build and shape something from the ground up.

What was the hard problem you felt Stackline was serving up for you?

Being at Amazon allowed me to see that almost every major brand was struggling to figure out how to run a modern e-commerce business. Some of the biggest consumer-centric brands in the world move their businesses and product lines entirely on the back of trends. I saw some of these giants slow their growth by as much as 20% simply because they couldn’t move inventory fast enough. I attribute that in part to the fact that in some of these organizations, many different people control many small pieces of the total e-commerce puzzle. I saw so much leakage of efficiency and opportunity because any given person in the company's e-commerce ecosystem didn’t have a full grasp of the data that impacted their part of the business, or the resources they needed, or the pacing of the market, or the difference between what a sales person does in e-commerce versus a salesperson in bricks. 

I spent six years watching every product category and every industry get completely destabilized. That’s when I saw Stackline in action for some of the big Amazon vendors. Stackline was harnessing the data to solve the big problems of understanding, and it was clarifying the direction these companies needed to move. Not only did Stackline have a powerful new approach to aggregating and serving up invaluable data, the company also had an executional arm to help organizations that did not yet have the internal resources to expend on mastering new platforms and marketing technologies, or perhaps not yet the expertise to dynamically analyze channel-specific metrics to improve returns. So I looked at Stackline’s data platform as the main reason to join, but I also liked the fact that we had the ability to help companies execute, which in turn could help us fund innovative solutions to the hard problems.

What are the primary differences between the brick-and-mortar ecosystem many brands have grown up in and the e-commerce ecosystem in which they’re now trying to find their next era of growth? 

A ton more information and infinite aisle space. If you go walk into a store, whether you like it or not, your mind will consciously or subconsciously say, 'These are my choices. These are the products I have to decide between.' Simply getting on the shelf in a brick-and-mortar environment immediately unlocked a book of business that didn’t require you to keep selling. With e-commerce, consumers have infinite choice all the time, and information is boundless. So it’s not just about convincing a buyer to put a product on a shelf. You have to constantly create processes for ingesting and making use of the data to change a product -- or think about pricing in real time, etcetera -- to continue attracting the customer. You’re not just going to gain hundreds of millions of dollars by achieving store placement. Companies that built a lot of their business on the back of winning the retailer instead of winning the customer had a lot of catching up to do. 

E-commerce demands a 24-hour-a-day, seven-days-a-week strategy. Traditional retailers are still great for people who want to narrow their search and get some in-person expertise, but the appeal of e-commerce is different, and often so is the customer. That requires a very different sales approach. 

Does Amazon have any existential crises about the paralysis that infinite choice creates for its customers, or do they see infinite choice as one of the great unalloyed benefits?

Because the Amazon search algorithm is primarily focused on serving up things that people are looking at and buying, it almost creates a very similar psychological behavior to an in-store model. The online shopper is often seeing the same thing other people are seeing. 

Apparel is a really good example. Search and discovery was Amazon’s single-biggest challenge, because in fashion and footwear, the SKU count is by the millions. Imagine what happens when someone types 'black t-shirt' into the search bar. In the background, Amazon is trying to find the optimal balance between showing them the latest and greatest and showing them what everybody else is buying. If you want to get behind ‘newness’ in a meaningful way, you’re actually doing that with less data, because you don’t yet have the data from clicks, conversions, and reviews. That’s the challenge e-commerce has: do we want to stay fresh by always prioritizing new, or do we want to build a business that says, 'We may not help you find new, but if you can find it for yourself, we’re going to have it'? That is the tango that Amazon and any major SKU-count intensive retailer is going to have. Because if you type in ‘black t-shirt’ right now on Amazon, I guarantee you're going to see something that’s been selling well on Amazon for years. It’s not likely to be something with a trend-forward cut or material. But that’s really the crux of Amazon’s biggest challenge in any category. How do you feature ‘new’ without losing the sale of something that’s likely more highly convertible? 

You built an amazing career at Amazon and could have spent the rest of your professional life there. What is it that you found so appealing about a company of Stackline’s stage?

I think the undefined element of a company this size is actually very peaceful for me. I was unsatisfied with the pattern of being given a problem and in almost the same sentence being told the desired design output. I love the fact that here we have problem statements floating around us consciously or subconsciously all the time, and we don’t have people telling us, 'Please go solve that problem, and when you do, make it look like this.'

I love being at a company where even the smallest projects start with, 'What are we trying to achieve as a business?' To be part of conversations where we are driving that clarity and challenging each other to think critically about the nearly infinite paths we could pursue is thought-provoking and intellectually enriching. 

What are we doing best for our clients right now?

One thing we do really, really well for clients is simplify. We take the many data points that surround and describe our clients’ e-commerce performance and distill them to a point where they can concretely explain the state of the business and the go-forward recommendations to the rest of their organization. 

The best signal of success for a Stackline deliverable is the number of emails exchanged in the aftermath. The more emails that swirl over something we deliver, the less intrinsically useful and insightful it was. The fewer clarifying emails we field, the more straightforward and helpful we were. 

We aren’t trying to solve problems in a way that proves we have oceans of data (though we do, and that’s critically important); we want to offer our clients answers that draw on the data and assimilate it fully, but ultimately simplify a course of action that allows them to quickly move the needle for their business. Our ability to do that stems from the fact that collectively, we’ve done so many different types of work for our clients and have a huge body of case studies to draw on. Our clients know the power of our software and see the caliber of brands we work with, so when we simplify hard problems, we don’t have to debate about whether or not we fully assembled and assimilated all the relevant inputs. That’s a given, which leaves us room and energy to debate the really important thing: what is the very best way to move forward?

How would you distill the problems we’re solving for brands in this digital ecosystem?

Every day we face a vast array of questions, but I think the single problem we’re all trying to solve right now is how to anticipate and accommodate the delta between what’s happening today in e-commerce and what’s going to happen tomorrow. Today and tomorrow will behave very differently, so we need to have access to the data that both retrospectively and predictively explains the nature of change. That’s why our software is so powerful. All of that relevant data is at our fingertips. 

I think we’re uniquely set up to help brands understand if they’re ‘doing it right’ today and if they’ve set themselves up operationally to be ‘doing it right’ two years from now from a channel, process, and product perspective. 

We’ve been talking a lot about the critical importance of data-backed decision-making. I’m curious if you think we’re putting a ceiling on the revolutionary capacity of capitalist innovation if we’re saying it always needs to be attached to the data.

I don’t think so. In my opinion, the best inventors still invent by working against the grain of data. But having access to the data that explains the status quo is what helps them size the risk. I guarantee that anyone making anything of seismic value today used the data to understand if their efforts will bear fruit. They may not have made a product because of what a data point told them, but they’re going to assess risk based on the data. And they will put whatever they create into the marketplace to gather feedback that helps them shape and maximize the potential. 

To those who would say there’s no artistry or creativity in modern business because of the onslaught of data, I would argue every act of creation begins with a reason. And that reason is almost invariably based on some collection of data points about the nature of reality. The artistry and creativity still exists -- and very much exists in the business world -- through the process of deciding which collection of data points should inspire innovation.

Stackline very consciously merges data and human ingenuity to solve problems in new ways. What kinds of people thrive in an environment like ours?

On the consulting and agency side, people who thrive at Stackline are comfortable urgently and creatively navigating ambiguity to find useful outcomes. They also have the capacity to build a high degree of client and team trust very quickly.

One of the primary ways we see people build that trust is by demonstrating my favorite Amazon leadership principle: learn and be curious. You have to want to work hard. You have to want to ask questions and be pushed to continually expand your areas of expertise. You can’t be someone who wants a job that’s handed to you, blueprint and all. You have to expect that you’re going to have more challenges in your week than successes. But the people who thrive here know that’s what makes the wins so much sweeter. We’re a bunch of like-minded people, so you instantly have that collaborative element, and we rally together around the shared understanding that things will be hard, and that’s okay, because we’re here to plow down walls and then build things that are better. If you have that mentality, you’re going to be an effective contributor. 

Tell me about the genesis of this first expansion office in Minneapolis.

Michael and I share the same vision about relationship-building. It can be aided by technology, but it has to be grounded in personal trust. The manufacturing community is small, and we want to be a trusted partner in that community. As we continue building important relationships with Target, Best Buy, and Walmart, we want the brands that sell to them to be able to get to know us and have access to us right in their backyard.

Of course, we also recognize that building a company culture remotely is a huge challenge. We wanted to give ourselves every opportunity to tackle that challenge in the right way. Minneapolis is an exciting market that in some ways feels similar to Seattle, but it also offers a high density of manufacturers and established retailers. It was a great fit for us. We have the right cultural development plan in place to really inculcate this new office with an intrinsically Stackline ethic while allowing it the freedom to pick up its own distinct Minneapolis and Midwest vibe. I’m from Minnesota, and I have a tremendous love for my home state and for the potential of Stackline, so all the pieces really fell into place.

Read more about the Minneapolis office and the new initatives Tom's team will take on in our latest press release.

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