From Intern to CEO & Founder: An Interview With Jess Ekstrom

Jess Ekstrom, the 25-year-old founder and CEO of Headbands of Hope, seems to offer an endless supply of leadership and business wisdom. In fact, our 30-minute conversation turned into an hour that I didn’t want to end because there was so much more to learn from her. That’s why it’s especially exciting to announce that Jess will be speaking at Leadercast Live 2017, where everyone will be able to soak in more of her leadership insights and purpose-driven entrepreneurship.

The Not-So-Basic Basics About Jess Ekstrom

Jess founded Headbands of Hope when she was 19 years old, as a junior in college, after interning with an organization that granted wishes for children with cancer. Her organization’s mission is purpose-driven: For every headband purchased, one is given to a child with cancer, delivered through hospitals, childhood cancer foundations, and special summer camps for seriously-ill children. During special events throughout the year, Headbands of Hope also donates a percentage of sales to cancer research. Since its inception in 2012, Headbands of Hope has impacted the lives of hundreds of thousands of people.

The first thing I noticed about Jess is that she truly embodies people-first leadership. She prioritizes her purpose over plans; manages a thriving business, and intentionally develops others. Throughout our conversation, Jess shed light on how she fosters a culture that builds employees into leaders who take initiative and who come to work motivated. In the Q&A below, I hope you’ll enjoy a preview of the powerful leadership principles you’ll hear from Jess at Leadercast Live 2017.

What kind of leader do you want to follow?
It sounds kind of strange, but I like subtle leadership. When you’re not even aware you’re being led because you’re inspired to move. It’s someone who inspires you to act without knowing it. Leaders evolve when they’re inspired. Not when they’re given task and responsibility. When there is a problem and you inspire them to come up with a solution is when true leaders develop.

What leadership lesson did you have to learn the hard way?
Even before I started Headbands of Hope, my idea of leadership was that it’s a position or title you were elected to, and leaders were the most vocal person — the one with all the ideas [who] speaks up. So, that’s who I was trying to be. But I started to realize that leaders come in all forms, and whether you’re elected and hold a title or not doesn’t matter. A leader is about what you do, not what’s on your business card. When I started to realize that leadership comes from within, my leadership style started to change.

What has been the most impactful leadership lesson you’ve learned?
I think that one of the most impactful leadership lessons I’ve learned is that it’s very easy to get mad and point fingers. As an example, we get 20,000 tags delivered to the warehouse; if something’s wrong and we can’t use them, it makes you want to rip your hair out. But you have to ask, “How can I prevent this from happening again?” What we do is send our printer a packet of colors, fonts, measurements, fabric—everything they could ever need or want . So instead of being frustrated, I [draw] inspiration from frustration.

How do you develop your own leadership skills?
I ask my staff to be honest. I created my company when I was 19. I hadn’t had much time in the workplace or been a leader before so I fully understand this a growing and learning time for me. So I put myself in [the position of my team] and ask, ‘What would I want from me? What is the kind of leader that I want to follow?’

How do you define that?
I think that in order to be a leader, you have to inspire your followers. Leadership is not about giving commands, it is about being driven by a purpose, communicating it to your followers and instilling it in the culture of what you do. It’s about a culture of why. Everyone has to be working toward one common goal. And that goal is the heartbeat of everyone’s job. One of the things that I do when anyone starts working at Headbands of Hope is to take them on a hospital donation so they can see the end result of all their hard work. We start with the ‘why’ and then go into the ‘what.’

How do you develop the leaders in your company?
I try to instill a responsibility in everyone, so that we all come up with solutions instead of looking to one person. We also have check-ins where I talk to them one-on-one—not just to review their performances, but also to ask if there’s anything I can do better.

Do you have advice for people who are trying to become leaders?
Focus more on your purpose and less on your plans.

[Not surprisingly, Jess often speaks to audiences on the topic, “Purpose Over Plan,” which encourages people to “look beyond the day-to-day or paycheck to the ‘why’ behind the work.” We’re sure to hear more on this topic at this year’s Leadercast Live, where the theme is Powered by Purpose.]

Speaking to a young leader with so much insight, wisdom and thirst to continue developing her mission and her leadership savvy was inspirational. Here are some key takeaways from our conversation:

  1. Challenge your perspective about what makes someone a leader. Try to define what it is you consider good leadership. Are you striving to be that kind of leader? And who are you following?
  2. Fight to turn your frustrations into inspiration. The next time something blows up, take a deep breath and then choose to look for solutions rather than point blame (even if the person you tend to blame is yourself).
  3. Know your “why.” Why are you showing up to work each day? How are your talents and skills being used? Know your why—your purpose—and use it to fuel your passion and leadership.

I hope you’ll join me at Leadercast Live 2017 to hear from Jess in person. And if you can’t attend in Atlanta, consider attending a host location near you.

Learn more by visiting and see Headbands of Hope in action on the Headbands of Hope Instagram account.

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