How a “Figure-It-Out” Job Launched Issy Cohen’s Advertising Career

Like many fresh college graduates, Issy Cohen didn’t have a neatly mapped-out plan when she walked across the stage to receive her diploma. What she did have was a willingness to explore. While she figured out her next move, she took a job managing social media for a local gym—and that seemingly small decision set everything else in motion.

Within a year, Issy landed a role as a social media coordinator at a boutique agency, kicking off a decade-long career in advertising defined by curiosity, adaptability, and innovation. Over the years, she’s moved through strategy, operations, and leadership roles, developing a nuanced point of view on how brands communicate, how teams actually work, and what it takes to build more human, effective systems in the industry.

Today, Issy is the Director of Operations for Advertising at healthtech company PurpleLab. Her career is a reminder that paths don’t have to be linear to be intentional—and that sometimes, the most meaningful momentum starts with a single, unexpected step.

What leadership skills are you most proud of having honed?

Empathy and compassion. These are the skills I’ve worked the hardest to build and the ones I rely on most. In advertising and in business, it’s easy to get caught up in performance and deadlines, but people don’t leave their lives at the door when they come to work. I lead with the mindset that my team members are humans first. I want to be the kind of leader people can come to with anything—without fear of judgment.

What are the biggest challenges you’re currently facing, and how are you solving them?

People often think operations roles are about fixing broken processes, but it’s really about shifting behavior. When you introduce a new system, it doesn’t take hold just because it makes sense on paper. You’re asking people to unlearn something that’s been comfortable for a long time. The real work is helping teams understand the why behind a change, giving them space to adjust, and creating consistency over time. Solving that challenge takes communication, patience, and a lot of repetition.

What’s something you do outside of work that makes you a better leader?

I’ve been an athlete my whole life, and a few years ago, I joined an adult softball league. Managing the dynamics of a team on the field—different personalities, competition, emotions—has given me even more perspective on leadership. It reminds me that clear communication, trust, and emotional awareness are just as important outside of work as they are in it.

What advice would you give someone starting out on the journey you’re on?

Being scared isn’t a weakness; it’s usually a sign you’re growing. Every major moment in my career—whether it ended in success or failure—started with fear. That fear means you care, and it means you’re stepping outside your comfort zone. People say that if you’re scared to fail, you’ll never succeed. When channeled in the right way, I think fear can be one of your biggest strengths.