From Nike to Urban Outfitters — Cyntia Leo’s 7 Tips for Rising the Ranks as a Brand Marketer

May 22, 2024

On the newest episode of "How The F**k Did You Get That Job", I sat down with Cyntia Leo, Head of Brand Marketing at Urban Outfitters. With a super impressive career spanning stints at Disney, Nike, and now Urban Outfitters, Cyntia has an insane amount of insights on what it takes to thrive as a leader in brand marketing.

Throughout our conversation, Cyntia opens up about her journey from a theater-loving kid in New York City to a marketing executive at some of the world's most iconic brands. She shares the lessons she's learned along the way about pursuing your passions, defining your leadership style, and creating more inclusive workplaces.

This episode is full of wisdom and inspiration for anyone looking to make their mark as a leader in their field. Be sure to catch the full conversation with Cyntia right here:

In the meantime, here are 7 tips from Cyntia to chew on.

1. Pursue your passions, even if they don't align with family expectations

Growing up, Cyntia's family expected her to follow in her father's footsteps and become an accountant. But from a young age, she knew her heart was in the arts.

"I kept telling my mom, at our school, we were the cool kids. It was a lot of fun, but from there I was doing a lot of creative writing as well, and I thought that I was going to work in magazines."

Cyntia pursued her passions for theater, music, and writing despite the pressure to take a more traditional career path. Her story drives home how important it is to stay true to yourself and follow your own dreams, not your parents’.

2. Align your work with your personal values and purpose

After a decade at Nike, Cyntia found herself being courted by numerous companies. But before jumping into a new role, she made sure the brand aligned with her personal values.

"While I was thinking about the next job, I'm fortunate enough that I had a lot of folks reach out to me via LinkedIn because of my tenure at Nike. And for a second, I started taking interviews for places that, I won't even say where, but I just wouldn't consume their product, right?”

Cyntia walked away from an opportunity at a company whose products she wouldn't use herself, even after getting deep into the interview process. She believes that to get to that next level in your work, you must genuinely stand behind what you're selling.

3. Be true to yourself and use your voice in the workplace

As a woman of color moving up the ranks, Cyntia has learned the power of staying true to herself while making her voice heard. Her advice to others:

"Hold on to your voice. Your voice, your point of view is super important. Make sure you're holding on to your voice, but also backing that up with strategy and data."

Cyntia encourages people from underrepresented groups to speak up and share their perspectives while also making sure their ideas are steeped in facts to make them hit home. The key is to bring your full, authentic self to the table.

4. Seek out mentorship and networking opportunities, especially with those who have broken barriers before you

Cyntia credits much of her success to the mentorship of other women of color who helped open doors for her throughout her career.

"Keep networking - it is half of the job. The doors that I've gotten into have been through other women of color. I would say 80% of the opportunities that I've had were other women of color who were either mentoring me, introducing me to the right person, or opening the right door for me."

Her story highlights just how important it is to proactively build relationships and seek guidance from people who have faced similar barriers and challenges. Their support can be game-changing.

5. Define your leadership style and expectations

As Cynthia has stepped into executive roles, she's gotten intentional about defining her unique leadership style and setting clear expectations with her teams.

"For me, I'm empathetic, but I'm also a hard worker. I expect a lot from the team. But I also want to have fun, and I want this to be a collaborative environment. I'm a big, big believer in collaboration."

Cynthia's approach aims to balance compassion and collaboration with a drive for excellence. She argues that the key is being upfront about what you value and how you'll measure success.

6. Take risks and be open to testing and learning

In her role at Urban Outfitters, Cyntia encourages her team to take chances and embrace experimentation, even if everything isn’t a runaway success.

"We want to be unexpected. We're going to test and learn a few things - some things are going to pop off and some things might fail. And that's okay."

To stay ahead of the curve, Cyntia argues that brands and individuals have to be willing to try new things, gather data, and iterate quickly. Getting comfortable with failure is a requirement to pushing innovation.

7. Recognize your career path may evolve over time as you discover new passions

Cyntia began her career in theater, working on Broadway shows for Disney, but she eventually realized she missed the world of sports that also shaped her as a kid.

"I grew up playing. I grew up in theater, but I also grew up playing basketball, and was an athlete. I was playing basketball at the time in New York City in an all boys league."

After her stint at Disney, Cyntia pivoted into a role at Nike where she could marry her love of storytelling with her passion for sports. Her story shows us how our interests can change over time, and our career paths won't always follow a straight line.

Untold stories from the world's most influential marketers. New episodes every Wednesday.  
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