Cynthia Cleveland: A Mastermind in Growing and Scaling Top-Tier Companies

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October 28, 2024

"Entrepreneurs often struggle to filter out distractions, and we help ensure their efforts align with their long-term growth vision."
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Cynthia Cleveland stands out as a pioneering leader in the business world, having served as CEO and President five times throughout her illustrious career. With over three decades of experience, she has played a pivotal role in generating more than $4 billion in global sales for esteemed brands like Universal Studios, Carnation Foods, Mattel Toys, Teleflora, and Imaginarium.

Recognized as one of the “Top 100 Visionary Leaders” by Real Leaders Magazine, Cynthia is also an active board member, contributing her expertise to over ten fiduciary and advisory boards. Her leadership extends to the Young Presidents’ Organization (YPO), where she has been a dedicated member for over 20 years, serving in key roles that unite a global network of 34,000 CEOs.

Currently, she serves at CEO Coaching International, where she leverages her extensive expertise to support leading entrepreneurs and CEOs in achieving substantial business growth. She is equipped to help individuals eager to advance their businesses, whether that involves enhancing profitability, establishing strategic partnerships, boosting sales performance, or creating lasting value, navigate the crucial steps toward transformative growth.

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Cynthia, you’ve had a unique path to leadership. Can you tell us about how you first became a CEO?

Cynthia Cleveland: I’ve always considered myself someone who navigates life with a bit of unpredictability, and becoming a CEO was no exception. It happened when I was unexpectedly pregnant and consulting for a company. I wasn’t planning on becoming a CEO, but one particular Christmas week changed everything.

I was called in to consult for a second company they owned, and at the time, I was working on a project involving collector dolls. One thing led to another, and I ended up offering insights that spanned beyond product development. I was analyzing consumer trends, sales margins, and business strategies. The owners saw my potential and offered me the role of CEO, even though I was seven months pregnant at the time. It was unexpected, but also a life-changing opportunity.

At the time, you didn’t have the qualifications typically expected for a CEO role. Did you feel prepared?

Cynthia Cleveland: I didn’t feel “qualified” in the traditional sense. But I’ve always been confident that I could figure things out. When I first took on the role, I didn’t have all the answers, but I was committed to finding them. A mentor once told me he hired me because I believed I could do the job, and that belief has carried me through many challenges.

Your fear of not trying seems to have been greater than the fear of failure. How did that fear of the unknown influence your decision?

Cynthia Cleveland: Looking five years ahead helped me make the decision. I realized that if I didn’t take the opportunity, I would always wonder what could have been. I wasn’t afraid of failure. I was more afraid of not knowing whether I could succeed. So, I went for it, and to this day, I’ve never looked back.

"The biggest lesson is that leadership isn’t just about the individual; it’s about the team."

Looking back at your time in leadership roles at companies like Teleflora and Imaginarium, what lessons have you applied to your current work?

Cynthia Cleveland: From Teleflora, I learned how powerful it can be to leverage licensing to drive revenue. Partnering with brands like Barbie and Oscar de la Renta opened up new opportunities. At Imaginarium, I focused on targeted marketing and understood how to segment customer bases for more effective outreach. Optimizing sales processes was another key lesson; shifting from door-to-door sales to direct channels proved more cost-effective. These experiences taught me the importance of efficiency, innovation, and personalization, strategies that are just as vital in today’s digital world.

Coaching has become a widespread term. How does your approach at CEO Coaching International differ from others, especially given the high-caliber leaders you work with?

Cynthia Cleveland: You’re right that the term “coach” has become overused, and not all coaches have the same level of impact. At CEO Coaching International, we focus on partnering with highly successful CEOs who are already leading significant businesses. Our goal is to elevate their thinking and help them scale their operations further. We aim to fuel growth, enabling clients to not only meet but exceed their expectations. Companies that work with us often experience growth at twice the national average.

For entrepreneurs who struggle with focus while trying to grow, how do you help them channel their energy?

Cynthia Cleveland: Entrepreneurs often struggle to filter out distractions, and we help ensure their efforts align with their long-term growth vision. Our approach is grounded in the belief that a broader vision fosters greater success, so we focus on expanding our clients’ perspectives beyond what they initially thought possible. Our systematic process involves assisting them in setting ambitious yearly goals, breaking those down into actionable quarterly objectives, and continuously refining their strategies. Success hinges on our method and the people we collaborate with, ensuring everyone is in the right role and that the team remains aligned and accountable.

Looking back at your journey, what’s the one lesson you’ve learned that you continue to apply in your coaching today?

Cynthia Cleveland: The biggest lesson is that leadership isn’t just about the individual; it’s about the team. Even today, when I coach others, my first step is always to assess the team. You need people who are not only skilled but who can evolve with the business and take it to the next level. If your team isn’t growing, neither is your company.

Jed Morley, VIP Contributor to ValiantCEO and the host of this interview would like to thank Cynthia Cleveland for taking the time to do this interview and share his knowledge and experience with our readers.

If you would like to get in touch with Cynthia Cleveland or her company, you can do it through her – Linkedin Page

Disclaimer: The ValiantCEO Community welcomes voices from many spheres on our open platform. We publish pieces as written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Community stories are not commissioned by our editorial team and must meet our guidelines prior to being published.

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Jed Morley

Jed Morley is the CEO of a leading payment processing service provider called PlatPay. He's also a featured VIP author on ValiantCEO. When he does not work with businesses to improve their payment processing solutions, he rides one of his 20 horses in his ranch in Utah.Click the author profile to find out more!