How organizational culture supports digital transformation: Insights from Moosejaw’s CTO
Insights · 11 min read

How organizational culture supports digital transformation: Insights from Moosejaw’s CTO

Natasha Wahid
Posted October 22, 2020

Article summary: In part II of our series on digital transformation, we hear from Michael Moore, CIO / CTO at Moosejaw—a leading U.S. retailer of outdoor goods and apparel that continues to evolve and transform to adapt to a digital-first world. In this post, Michael discusses digital strategy, how Moosejaw fosters innovation, and the importance of C-level support to facilitate digital transformation success.

ICYMI, check out the first post in our series: Margaret Wise, Chief Revenue Officer at Arke, a digital consultancy, discusses how to lay a foundation for strategic digital transformation.


Company culture is a key piece of the digital transformation puzzle

The terms “customer-centricity” and “digital transformation” are often used in the same breath. Most business leaders understand that a stellar customer experience is essential in today’s world, but many struggle to operationalize customer-centricity. It quickly becomes just another buzzword.

One method to make sure your company maintains focus on what your customers actually need and want is experimentation—that is, continuous testing, learning, and iterating.

According to original research from FullStory, more mature digital experience organizations are more likely to encourage testing and learning than their less mature counterparts. And they are 47% more likely to report that they actually iterate on a digital experience once it has been shipped.

"To provide a digital experience that actually meets customer needs, digital leaders must be willing to put their ideas to the test. Because—most of the time—the experience that companies design is not the experience customers are seeking. — FullStory’s "State of Digital Experience 2020 report

A test-and-learn approach is critical to achieve customer-centricity. It asks an organization to have a constant pulse on customer feedback, pain, and behavior—and to propose and deliver customer-motivated changes quickly. Every test should get you one step closer to a more perfect customer experience.

That said, company culture must support experimentation—and for many organizations, this is a stumbling  block. A test-and-learn culture means everyone, at every level in the organization, checks their ego at the door. It means that ideas can (and should) come from anywhere, as long as they are rooted in evidence. It means transparency is celebrated and encouraged, whether an idea is a winner or a loser. It means that good ideas actually get put to the test and then implemented.

It is this test-and-learn energy that separates innovative companies from those that find themselves stuck and often left behind. In the following conversation, Michael Moore, CIO / CTO at Moosejaw shares the cultural norms and practices that help the almost 30-year-old retailer stay on the cutting edge.

"Innovation is at our core. Top to bottom. People come to Moosejaw for it. It’s a part of the fabric. — Michael Moore, CIO / CTO, Moosejaw"

The innovator’s perspective: Michael Moore, CIO / CTO at Moosejaw on culture and innovation

Q: Moosejaw began as a physical retailer back in 1992—would you say you’ve gone through a digital transformation?

Michael: “Digital transformation” is a never-ending chase, right? We’ve certainly been ahead—we were doing ‘responsive design’ before there was a concept for it, for example. But we’ll never be done. We’ve always tried to be cutting edge in terms of how we leverage technology at Moosejaw, and that hasn’t changed. There are so many competitors in our space, so it’s something we have to do to continue to differentiate ourselves.

Agility and innovation is key for us. We have a fairly small tech team, but we’re fast. When the business has ideas, we can usually implement them fairly quickly. We have several projects earmarked for 2021 that I can’t give too much detail on yet, but we’ll be the first in the industry to introduce some pretty neat features. So stay tuned.

Q: Do you think that ‘cutting-edge’ culture is unique to Moosejaw in your space?

Michael: I don’t think it’s unique anymore but it certainly was. Our marketing teams and our technology teams have always worked hand in hand—even before the CTO / CMO revolution happened 5, 10 years ago. We have naturally conflicting interests, but we’re also natural partners. They’re our biggest customer; they’re trying to come up with the craziest ideas and unique things to differentiate us in the market and it’s always been up to IT to accept that challenge and figure out how to bring those big ideas to life.

Q: Is digital innovation a consistent conversation at the C-level?

Michael: Yes. We live it. The CEO lives it. I live it. One of our core company values is ‘only do cool stuff’, which is one that feels particularly applicable in IT. We’re constantly thinking of ways to innovate and stay cutting edge.

Of course, it’s getting more challenging. Most companies today—including many of our competitors and other players in the space—understand the importance of digital innovation and are investing in it. But innovation is at our core. Top to bottom. People come to Moosejaw for it. It’s a part of the fabric.

I’ve worked at companies where the culture is a roadblock to innovation. Some cultures can’t be saved. But if you’re in a company where people are open to something new, to a shift, you can be a change-agent. You just have to prove it. You have to walk the walk. For any change you want to create, you just have to prove it.

"If you’re in a company where people are open to something new, to a shift, you can be a change-agent. You just have to prove it. You have to walk the walk."

I still have to do that constantly at Moosejaw—and that’s how it should be. But I’ve had enough victories because I work to prove an idea and then I often get to see it implemented company-wide. And you just build on those successes.

Q: So many organizations struggle to create that agility you mentioned. How do you foster and maintain a quick-moving, agile team?

Michael: Our people are critical to helping us stay agile and efficient. So the obvious challenge is keeping an all-star team engaged and in place. Getting folks to buy into what we’re doing is priority number one for me.

Great culture comes from the top, but technology is also a different beast. We’re nerds. We like to write code, we like to dig into the nuts and bolts of things—and sometimes business priorities don’t make a ton of sense to us. When the team is excited and motivated by the work, that’s when projects are successful. And we’ve done a pretty good job of fostering that excitement over the years.

"The team likes to see projects through to completion, see their work on the website, and see their efforts move the needle. That’s the fun part. That’s the payoff."

It’s a mix of showing business impact and creating space for innovation. The team likes to see projects through to completion, see their work on the website, and see their efforts move the needle. That’s the fun part. That’s the payoff.

Q: What are the most important components of an effective digital strategy?

Michael: "Digital strategy" is kind of a buzzword. Really, it just comes down to a few questions: Do you have what customers want, do you make it easy to find, do you make it easy to purchase, and then do you follow through? Is your customer service top-notch? (I believe ours is.) That’s how you win loyal customers.

How many times have you gone to a site and you just didn’t have a good experience? It doesn’t even take a horrible experience, it just takes a couple of questionable interactions.

It’s my job to make sure that our great outdoor products are easy to find. That the customer’s experience is error-free. That people are able to add things to their cart and check out seamlessly with whatever payment method they want to use. Then it’s on our operations department to make sure they get their stuff as soon as possible.

You’ve got to nail that. If you can nail that, then you can build on that trust with marketing and branding and whimsical flavor and really solidify those customer relationships.

Q: For many companies, ‘digital’ is off to the side. How does Moosejaw view digital?

Michael: Ecommerce is our primary sales avenue. We love our stores and continue to invest in our stores—there will always be folks who like to come in and have that in-person experience. But 80 to 90 percent of our business is done online. Our company founders were passionate about technology. People migrate towards what they love and our founders loved technology, they liked to be on the cutting edge, first-to-market, early adopters and that culture is what Moosejaw was built on, and it continues now.

Q: Are there specific digital objectives that are top-of-mind for you right now?

Michael: We want to get back to innovating. The last few years, we’ve been entrenched in a necessary platform migration, and now the focus is on how to best leverage it. We’re on this latest, greatest engine but now we’re thinking about how to increase our top speed, how to navigate the racetrack. In 2021 and beyond, we want to get back to innovating, being cutting edge, and we have a few very cool projects that are going to be fun to work on in the next year.

Q: What does innovation look like at Moosejaw? Is there a process?

Michael: You know, there isn’t a process per se. I think you have to be inspired. From our CEO to our marketing leads, to our warehouse and customer service folks, there’s a hunger for innovation. You’re reminded of it everyday. Innovation and ways to innovate is always a top-level objective. No idea is too outrageous. We welcome them.

"There’s a culture here that encourages people to ask, to suggest. We inspire each other to come up with different ideas and concepts—and we implement some of them."

For example, our CEO hosts a company-wide weekly meeting. He does a Q&A and no question is too silly or absurd. We do get some silly questions, of course, but we also get a lot of serious questions. There’s a culture here that encourages people to ask, to suggest. We inspire each other to come up with different ideas and concepts—and we implement some of them. And that’s the payoff.

Q: Is it fairly common then for ideas that are bubbling up to actually be implemented?

Michael: It’s common. It happens frequently. If somebody has an idea that feels worthwhile, no matter their department, it goes into our standard vetting process. Usually it would fall to IT to create a LOE (Level of Effort) to understand the level of effort to implement the idea. And if it makes sense, we’ll try it!

Our CEO is willing to gamble, which is a gift. He’ll let people take calculated risks. Sometimes they pay off, sometimes they don’t. And that’s ok. We’ve had some projects fail but we’ve had a number be really successful. Until they all start to fail, we’ll keep doing it this way.

We value learning. We do post-mortems on projects whether they fail or succeed—there’s so much to be learned in either case. If a project was successful, the question is often: How can we replicate this success in other areas, compound it in other ways? When a project fails, we try to look at it objectively and a few questions like: Did we just do it wrong? Is this something we can try again in a different way? Does this concept just not work for us? Is it misaligned with our brand, our culture?

Failures and successes are equally important.


In the final post in our series, we’ll hear the disruptor’s perspective. We spoke to Bjorn Borstelmann, affectionately known as “Cap’n Bjorn”, CEO of Pirate Ship, a company that makes shipping packages fun and cheap for small businesses. Cap’n Bjorn shares his thoughts on “digital as the future” as the leader of a digital-first company. Coming soon!

Did you miss the first post in our digital transformation series? Click here to read “How to do digital transformation” and get insights from Margaret Wise, Chief Revenue Officer at Arke, a leading digital consultancy.

Curious about how FullStory facilitates a culture of customer-centricity? Read Julian’s story and discover how his team at Thomasnet used FullStory to pivot in the early days of the pandemic and how the platform has become a part of their customer-first company culture.

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