Making Strategic Career Moves With Mindy Grossman
July 29, 2021
In 2017 Mindy Grossman became the president of WW, formerly Weight Watchers, and has been driving transformational change ever since. Prior to that she transformed the Home Shopping Network (HSN), launched Polo Jeans Company for Ralph Lauren, and accelerated the growth of Nike’s Global Apparel business.

Mindy joins our founder Dee Poku-Spalding in a conversation about making strategic moves and how those moves affected the trajectory of her career.

Dee: Prior to WW you were the CEO of HSN and before that you were the Global Vice President at Nike. What were the top-level tactics that went into attaining these major roles?

Mindy: My career has been anything but linear. However, what looks like a lot of zigzagging has actually been very strategic. I spent the first 15 years of my career in the menswear industry, working for designers such as Jeffrey Banks, Willie Smith, Tommy Hilfiger, and Ralph Lauren at a time when there weren't very many women in the men's wear industry. At one point, there were changes that I had to make because I knew that I wasn't going to be given opportunities to move ahead.

When I finally did get an opportunity to start Polo Jeans Company, it was after spending a year as Head of New Business Development at Ralph Lauren. That year was very pivotal for me because it was really the first year that I had more of a corporate role and less of a people leadership role. It also gave me the opportunity to work across so many industries and look at so many things, which also made me realize that no matter what industry you're in, you can't just stay in your lane, you have to have the purview of what's happening everywhere.

Dee: Your decision-making process is so fascinating. You approach each role with a four-page pitch deck where you really lay out your vision. You write things down, not the role, not the company, but the things that you want out of a new role, then you proactively give that list to people that come your way. That is a great way to pivot in your career. Can you expand upon that?

Mindy: Sometimes we forget, we're not defined by the industry that we come out of, we're defined by the attributes of our leadership qualities, and what we bring to the table. One example of me manifesting a position came when I gave my list to recruiters. A couple of months later, I got a call saying I needed to have lunch with Barry Diller and I needed to go run IAC retail. I had never even heard of it. They said, well, it's a home shopping network and a portfolio of catalog brands in need of transformation. I said, give me two weeks. Let me formulate a thesis of if I were to do this, what would I do - I think that's really important in any conversation.

So with that, I had lunch with Barry, I pitched to him my thesis like you'd pitch a VC. This is a man whose mantra is 'risk-taking and boldness is the essence of transformation'. He told me to go for it. I'll never forget that conversation with Barry. I had no television experience, no media experience, and only a little digital experience. However, I literally listed what I did have, and what I could add value to.

I pitched to Barry just like the many entrepreneurs who have made pitches to VCs about businesses that don't exist. It's not very different.

Dee: Do you consider yourself an entrepreneur or an executive? Or kind of a hybrid? You seem to have a lot of empathy for entrepreneurship.

Mindy: I think it's less about a model and more about a philosophy. I relate very much to the entrepreneurial world because in most cases, entrepreneurs see an opportunity and they see something out there that isn't being served. What they have to do is be able to create - whether it's the product, or the environment, or whatever the business is - in order to provide that service. That's how I think of things as well, which is probably why I have such an affinity.

Dee: So obviously, every time you change roles, you go into an organization where you're inheriting a culture and a team. I'm interested to know how you approach that every time and how you think about building loyalty and respect amongst a new team?

Mindy: I talk a lot about the qualities of leadership, which are genderless, right? It's the ability to set a vision and a strategy and align the organization against it, it's the ability to create a culture of humanity. You know, I started talking about vulnerability and empathy as strengths, way before COVID, when people actually defined it more as a weakness. Everyone realizes now that, ultimately, it is a strength.

Dee: Because we are a community of women helping other women succeed, who are your three go to's?

Mindy: I am innately a curious person. And if I see people doing things that are interesting, or having an impact, I reach out all the time. My whole focus has been, I will be successful if I help make other people successful. Because of that, I have a network of women. I always ask, who are you going to call it in the morning when you're having a meltdown? If you can't think of someone, you haven't built the right authentic relationships. Building authentic networks of support is just so important. And I'm blessed to have that.



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