My Career Path: Interview with Jenifer DeSofi, Global C-Suite Executive & EVP

This month, we had the pleasure of speaking with Jenifer DeSofi, Global C-Suite Executive & EVP, about her career path and the decisions that have contributed to her success. Here at Stage 4 Solutions, we are committed to supporting professionals’ career growth, and we believe that one way to enable success is by learning from leaders.

Jenifer is a multifaceted enterprise leader who operates with a consistent blend of art and science. Throughout her career, Jenifer has led all aspects of Product, Brand, and Experience creation from design through delivery for some of the world’s most beloved and iconic brands. She has a proven track record for creating and launching new brands from identified whitespace, repositioning and reintroducing legacy brands at critical pivot points, and maximizing and building continued relevance for mature brands. Jenifer is a strategic, values-based leader with 25 years of experience in complex, multinational, publicly traded companies.

Most recently, Jenifer held the role of EVP, Head of Global Product Creation for the consumer products division at The Walt Disney Company. There, she had the honor of leading a global team of over 2,000 employees across creative, design, merchandising, retail strategy, and supply chain, and bringing the most beloved products in the world to fans around the globe. Her scope spanned 130+ categories, representing over $60B in market share, and was accomplished through a strategic, multi-channel, multi-brand approach.

Prior to Disney, Jenifer spent 15 years with Levi Strauss and Company, leading merchandising, product design, and marketing. During her tenure, she drove significant business value by maximizing the portfolio and segmenting the marketplace through market-leading product innovation, new brand strategies, and new consumer acquisition.

Feel free to connect with Jenifer: LinkedIn

When you were at San Francisco State University, what were your career inspirations?

Jenifer: When I first started college, my plan was to get a business degree and then go to law school. I had big aspirations to be a sports attorney for myriad reasons. To support myself during college, I started working at Nordstrom. I always say, “The career that I have been in for 25 years, I fell into it by accident.” While working at Nordstrom, I realized that I had this love of “Product.” I never really knew what Merchandising, Design, and Product were. It was not really in my vernacular, but when I started working at Nordstrom, I realized that I was truly born to do this, and it became a love of mine.

I love matching people with brands and products that bring them joy. I credit Nordstrom for helping me develop many of the leadership skills and retail management strategies I possess. It was a great place to learn about the industry, lead people, and drive results through different strategies. At Nordstrom, I had the chance to learn how to build a true competitive advantage, employ honest sales tactics, drive great results, and excel in customer service. While in college, thinking I was going to be a lawyer, I fell into it, an industry that I had no idea I was destined for. I credit a lot of where I am today to the job I took while I was in school. It was by accident, but I think the universe had a plan for me.

How did you decide on your first professional job?   

Jenifer: You could say that Nordstrom was my first professional job, but it was happening concurrently with school. After spending five years at Nordstrom, when I was 23, I realized that I wanted to get closer to the source on product. At Nordstrom, I worked with the buying office, where I had the opportunity to assist in selecting and purchasing product lines. However, I wasn’t in the place where I was making the product, and I wanted to seek that out. I started looking for roles that would allow me to make the product. That is what brought me to Levi’s, which I would say is my true first professional job.

It was really interesting how I chose the job at Levi’s. I have these pivot points in my life, and the job at Levi’s is a pivot point for me. I was offered two jobs in the company at the same time. One of them was with the established Levi’s brand, and the other one was with an up-and-coming set of brands that they were building to reach a different part of the marketplace. It was more of the entrepreneurial side of the company. I decided to join the new brands to leverage the equity of Levi’s to build something new. What appealed to me was the opportunity to be an entrepreneur with the support of a company that had been around for 160 years.

Starting something from scratch allowed me to build out the brand value proposition, consumer strategy, and how we wanted to show up in the marketplace. Looking back, I credit that decision for where I am today because it was such an entrepreneurial role where I was doing it all. Not only was I utilizing my core competency in merchandising, but the role provided me the opportunities to leaf in marketing, design, and act as a general manager. I could leverage my merchandising skills to understand the rest, which, if you fast forward to today, is where I am now. Making the decision at 23 to pursue the more entrepreneurial path was a good one, and I believe it set me up for where I am today.

Can you tell us about your engagement with WE ARE THE BOARD as a member?

Jenifer: After 25 years of moving at a hundred miles an hour and reaching the C-suite level, I left Disney at the end of 2022 and decided to take a full year off and pause. Having reached that milestone after 25 years, I felt it was important to understand how to solidify myself as a whole person. The way my life was running, I had two perpetual to-do lists: work to-do and personal to-do. The work list always took priority, receiving 150% of my energy, while the personal list got left to the wayside and became nice-to-have. I took this moment to say, “How do I take a year off to focus on what used to be nice-to-haves and make them must-haves to complete myself as a whole human being?” I needed to figure out what I wanted the next 20 years of my career to look like.

It is a privilege and such an amazing growth moment. You can take everything that you have done in 25 years of your career and combine it with all the things that you put off or did not focus when you were so busy in your job.

Fast forward, it has been a year since then. I finished that year at the end of 2023, and with that, it was time to start thinking about the next chapter of my career. I have been actively looking at what I want the next 20 years to look like. Through this, I have done some great consulting and have met WE ARE THE BOARD, which is an amazing community. I could not be happier to be part of this group of like-minded people, high-level executives who have taken career pivots and gone into consulting or gone fractional, focusing on the future of work. We are exploring a new way of work – how we think about the recent shifts in the zeitgeist and how we can be better together as a community. We call it creative salon meets business consultancy, which I think is a new way of working where it is not just about driving results, but also about being a creative entity that comes up with the way that we do things in the future. We share best practices that support each other and come together to brainstorm while running our businesses, being entrepreneurs and consultants. It is a great community that I have found in this next phase of my career, and I am pleased to be attached to it.

As you progressed through your career, how did you assess new opportunities?

Jenifer: I came up with three key factors to assist me in how I progressed and looked at the opportunities. First, it starts with the brand-building opportunity. I have always been a person who seeks out the opportunity to build brands. There is nothing greater than creating products and brands that connect with consumers and bring them joy. I always look for opportunities to build and develop brands, create products, and connect with people through them.

The second factor for me has been the leadership opportunity, meaning my ability in those leadership seats to invest in people and build teams. I love nothing more than seeing people develop and reach their full potential. Witnessing the power that comes from a highly functional group of people that is dedicated to driving business success and to each other’s success is an amazing feeling. When I assess opportunities, I make sure that I have the opportunity to truly invest in building teams in a way that offers advancement opportunities for the teams and supports how they can work together.

The third factor is the potential of the role, the business opportunity, and the untapped potential of the brand or product. I love seeing how, when the flywheel gets going, you start spinning and realize that you have uncovered some diamonds. You have been able to build the team, a brand, and a product in a way that is now addressing the marketplace, bringing joy to consumers, and helping that brand reach its full potential. It is about how I can bring my leadership skills and my talent to the table to reach the potential of whatever that business is.

What factors led you to join Disney after spending over 15 years at Levi Strauss & Co.?

Jenifer: Back in 2018, I declined the first outreach from Disney because I was so happy in my role at Levi’s and dedicated to the mission I had signed up to lead, and I was not interested in relocating or leaving Levi’s. Disney reached out again a month later, and I decided to take the call as an exploratory. I wanted to understand what was going on in the marketplace, and what the role was. I honestly believe it was one of the best decisions I have ever made to take that call and explore the job opportunity.

I fell in love with the vision that Disney laid out for the pivotal role that I would play in that new chapter of growth for the company. By taking the job at Disney, I moved to Los Angeles, which is a city I have fallen in love with and where I am meant to be. This opportunity gave me the honor of stewarding some of the world’s most beloved brands and leading an insanely talented team of global talent. I credit taking the second call and engaging in that exploratory process as one of the best decisions I have ever made because it led me to where I am today and helped shape me as a person.

That decision also challenged me to step out of my comfort zone. I had been at Levi’s for 16 years. It was one of those moments that led me to leave Levi’s, which might seem crazy, but it also pushed me out of my comfort zone and helped me grow and level up to a new spot. That is how I made that decision.

What has surprised you the most in your career?

Jenifer: The thing that has surprised me the most in my career, which is probably more a realization than a surprise, is the impact of leadership and how that powerful ripple effect makes its way through an organization and into the culture, whether it is good or bad.

I have seen instances where you have fantastic leadership; how they run a company ripples through to build the culture and leads to amazing results and sustained teams. I have seen other instances where leadership has faltered. If you think about a stone in a pond and how it ripples, it starts small, but it ripples out pretty large, especially when you have big organizations. It has been a surprise to me how small decisions, good or bad, can affect the culture of a team and the work that the leadership team needs to do to lead those teams to success and deliver business results.

This is something that I have reflected on a lot over the last year; I want to understand how we can put more meaning and more strategy behind this as we think about the future of work, how we build culture, and how businesses succeed or do not succeed. I do not know if surprise is the right word, but I think understanding the true power of leadership and how that ripples through culture has been one of my most significant realizations throughout my career.

Can you tell us about an important career risk you took?

Jenifer: I think I am sitting in it as we speak. This career pause that I chose to take a year ago is probably one of the biggest risks. To step away from a 25-year career with the trajectory that I was on and intentionally take time to reevaluate what I want the next 20 years to look like and how I want to show up as a complete individual is one of the bigger risks I have taken.

It is to be seen if this risk will be successful – I think it is going to be. I do hope that I will look back at this decision as a defining moment in my career, laying the proper foundation for the next 20 years of not only what I can do in my career but also what I can do for the industry, for people I mentor, and for shaping the future of work.

What is one of the biggest challenges you have faced in your career, and how did you overcome it?

Jenifer:  I climbed the ranks in my career pretty quickly. I started my career early when I was in college, and I almost had a 5-year head start because of it. I was almost always the youngest person at the table and most of the time, I was the only millennial on the leadership team. That, coupled with the fact that I am a woman and half Cuban, meant that I had significant hurdles to overcome when it came to garnering respect and advancement. Like many people, including women, people of color, and those from more marginalized backgrounds, you often feel like you have to work twice as hard and over-deliver compared to your peers to garner the same accolades and respect. Unfortunately, there is probably not a formula for overcoming that yet, but I think we are working on that as a society. I did have quite a few fantastic female mentors who I still lean on today. I talk to them regularly, and I am forever grateful for those people in my life.

When I reflect on overcoming this challenge, whether it is being the youngest or being of a different race, ethnicity, or any other obstacle, I think the way I have looked at it is, “How can I be part of the change? How can I help the next generation not face the things that I faced?” Overcoming this challenge has involved making it different for those who follow me.  When it comes to my leadership style I am deeply committed to empowerment, mentorship, and information sharing versus hiding and keeping things close to the vest, and promoting diversity in all forms. I cannot say that I necessarily overcame this challenge, I struggled and felt like I had to work a lot harder to advance. I believe that how I empower that not to be the case for others going forward has been a real North Star for how I lead and how I act as a leader.

How do you balance your professional and personal goals?

Jenifer: I am probably not a great role model with this if I am being honest. As I mentioned earlier, I had two perpetual to-do lists, and the work one tended to get all of the energy. I say that with a caveat, though: I love the work I do, and I feel like it is a part of me. Work has been so much of who I am as a person that I do not feel like I have missed a lot on the personal side because so much of my work involved what I wanted to do as a person – whether it be the making of the products, connecting with the consumers, or traveling around the world. It was truly what I wanted to do personally.

I do not know if I am the best role model in balancing everything between work and personal life. However, the pause I took has provided a valuable opportunity for reflection. It has helped me identify areas where I may have overcommitted to work and need to establish better boundaries and focus on the personal side, whether it is education, spending more quality time with the people I love, or reprioritizing mental and physical health to achieve a better balance. I believe I am learning how to balance things better now. Falling into a profession I love and putting 150% into my career was also investing in my personal life because they were so interconnected for me.

What advice would you give to your younger self? Younger professionals?

Jenifer: This question takes a lot of reflection. I will narrow it down to three things. Firstly, I think it is really important to define your values and be very clear about not capitulating on those values. When you are making money or being successful, it can be so easy to give in on your values. What I found is that when I was true to my values, success came with it. When I capitulated on my values, even if success came with it, it did not feel good. So, I always say, “define your values.” What are your non-negotiables? What are the things that you personally stand for, and why? And do not compromise on them.

Similar to what we talked about in the last question, I would say, “If you have the opportunity to do it, do what you love.” When you think about strength-based leadership, it is all about how much more you can get out of a person when they are doing something that they are good at or that they love. When you are doing what you love, your 100% becomes 150% because you are so involved in it, and it is so much of what you want to do and who you are. It is super important to do the things you love if you can.

Lastly, one thing I always would tell my teams, and sometimes remind myself, is to be willing to break that mold. I always say, “Get comfortable being uncomfortable,” and I believe this is crucial when you think about how you are going to set your life on a path. If you are constantly comfortable, you are probably not reaching your potential. So, in order to truly get to that potential, get comfortable being uncomfortable because when you are uncomfortable, you know you are building new muscles, learning new things, and stretching yourself. Be willing to do that and be willing to break the mold.