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The influential women in Gap’s head office talk transformation, tech and leadership

Teri List-Stoll keeps a colorful sign in her office that captures her approach to her life, business and career. She was at a street art fair with her daughters when she stumbled upon the bright pink, green and orange sign that reads: Laugh. Believe. Take Chances. Trust Yourself.

That philosophy has carried List-Stoll’s career from Deloitte to leadership roles at companies with household names, including Procter and Gamble and Kraft Foods. Now she is the executive vice president and chief financial officer of Gap Inc., the much-loved $16 billion global clothing and accessories retailer, where she is reimagining the company’s relationship with customers – a transformation enabled by the Microsoft cloud.

We caught up with List-Stoll at a Professional Business Women of California event, where she was being honored as a retail industry leader and innovator. List-Stoll and her colleague, Gap CIO Sally Gilligan, shared their vision for the Gap, tips for up-and-coming young leaders, and the best career advice they ever received.

A photo of Teri List-Stoll.
Teri List-Stoll.

TRANSFORM: Teri, a lot of people know what a CFO does, in general. What is your specific focus?

LIST-STOLL: I think some CFO roles can be artificially narrow, focused just on the finance side of the business. What makes my role at Gap interesting to me – and hopefully valuable to the company – is that I approach it with a broader business mind: I focus on the strategy, then the execution of the strategy, which leads to financial results we can be proud of. That makes it intellectually challenging and fun.

TRANSFORM: Did the two of you have mentors along the way?

LIST-STOLL: I’ve had lots of mentors over the course of my career: People who have encouraged me, advocated for me, told me when I messed up – which sometimes you need to hear. The person who had the most impact came along when I was at Deloitte, just out of undergraduate school. There was an assignment in the firm’s national office that required me to move to New York, and to compete with the firm’s best and brightest.

I had the naivete to tell this mentor that I was terrified.

He looked at me and said, “Teri, what are you saying? If you don’t have confidence in yourself, how can you expect me – or anyone else – to have confidence in you? Go do it!” It was life changing. I moved to New York from the small town where I was working, and it totally changed my career trajectory.

GILLIGAN: I had a good mentor who told me: “Go slow to go fast.” This has brought a lot of wisdom in my career [laughter].

TRANSFORM: What does “transformation” mean to you at the Gap?

LIST-STOLL: From my perspective, transformation is the combination of having a true business vision for value creation combined with an execution plan that gets you there. Many of us have been guilty of being swept up in activity – which is all interesting, and fun, and challenging. However, without a real focus on where you’re trying to go and what you’re willing to do – and not do – to get there, you’ll never arrive. For me, transformation all hinges on quality execution, and quality execution is hard. It takes planning. It takes patience. It takes funding. It takes collaboration – all things that allow you to achieve the results you want when you use the word “transformation.”

A photo of Sally Gilligan.
Sally Gilligan.

GILLIGAN: Often there is a vision and a strategy, then a jump straight into tactics. What’s missing is the hard, operational planning required to build a roadmap to the desired capabilities. Once this operational planning becomes part of your culture, it also becomes how you execute and do business. And that’s how you get real transformation rather than a one-time, episodic event that doesn’t deliver impact.

TRANSFORM: What is the No. 1 capability you want to put in the hands of your employees?

LIST-STOLL: For me, no question, it’s simplification. It’s frustrating to spend eight hours trying to get clean data out of a system instead of analyzing the data, leveraging the data and doing something with the data. To the extent we can simplify the work and focus on what really matters to the business, people are happier, and the business performs better.

Productivity is a major pillar in our new strategy. We’ll deliver that productivity by re-engineering processes to eliminate old legacy work, and by leveraging technology – including AI and machine learning – that takes human error out of the process and provides that productivity we’re looking for.

TRANSFORM: Is there a big, technology-focused business initiative you can share?

GILLIGAN: There’s a whole suite of capabilities that didn’t exist for us 10 years ago, even five years ago. It’s one thing to be responsive on a small scale. But when you’re our size and going all the way from supply chain to customer and back again, you must bring the right technology to bear.

For instance, we’ve transformed our operations to drive a demand-based operating model. While that’s been around for a while in industries like technology, most retailers still push out their products on a seasonal basis. At Gap, about 50 percent of our assortment is now demand-based. We can deliver this at scale because we’ve built distributed computing into our inventory management systems. We’re using some elements of machine learning, and different algorithms to help us test and learn.

 TRANSFORM: What role do you see Microsoft playing in retail?

GILLIGAN: It begins and ends with the customer. Where is she going? Where does she want to go? How does she live her life? Data and insights are part of it. There is also a cultural shift to become more data driven. Retailers can create capacity to do greater things that have greater impact by not just looking at new things they can do, but at what they can stop doing. What kinds of opportunities can machine learning and automation open up?

LIST-STOLL: Retailers have a real opportunity to partner with Microsoft in a strategic way to find solutions, grounded in technology, to their business problems. There is real power in bringing all of Microsoft’s capabilities to bear on all of a retailer’s business needs – as opposed to bit by bit by bit. When we made the decision to partner with Microsoft, we knew we would have access to Microsoft resources and that they would all be brought to bear on our specific business issues.

TRANSFORM: How have Gap and Microsoft grown together?

LIST-STOLL: In the last few years, we have noticed a real pivot in how Microsoft engages with us. In the past, Microsoft seemed like a transactional product company. Now, when we interact with Microsoft, we see a powerful mindset at work. Microsoft wants to partner with their customers in a strategic way, really understand their business problems, and bring a suite of capabilities to bear that solve those problems.

TRANSFORM: What advice do you have for emerging women leaders? What advice would you have given to your younger self?

LIST-STOLL: Work hard. Be confident. Find your voice. And use it to get a seat at the table. Those are things you hear all the time, but they really are important to be able to gain influence. Laugh, because you have to. Believe in what you are doing and who you are. Take some chances – some things will go well, and some things won’t, but you must have the courage to try. And trust yourself – you can do it!

GILLIGAN: The best advice I ever got is, find your true voice. Don’t execute someone else’s voice. Find your own voice and find your place. It’s incredibly empowering.

Photos courtesy of Gap Inc.