Cynthia Cleveland | Leadership Lessons From a Five-Time CEO/President with Over $4 Billion in Revenues

Cynthia Cleveland is a five-time CEO/President who has led companies that have generated over $4 billion in worldwide sales across consumer products, entertainment, and retail. She is an expert in developing, translating, and monetizing intellectual property rights into major global consumer brands and new businesses across diverse industries. Her 30+ year career has spanned well-known companies including Universal Studios, Mattel Toys, and Teleflora driving significant growth and profitability. She has also worked on brands such as Barbie, Hot Wheels, Jurassic Park, Myers Briggs assessment, and Imaginarium.

Cynthia was named “One of the Top 100 Visionary Leaders” by Real Leaders Magazine. She is an experienced board member having served on over 10 boards including top leadership in Young Presidents’ Organization (YPO), the premier leadership organization of chief executives having served as Chapter Chair, on the regional board and selected for International Leadership.

Cynthia Cleveland, Partner at CEO Coaching International, is John Corcoran’s guest in this episode of the Smart Business Revolution Podcast. They will be talking about Cynthia’s leadership experience in different companies, how businesses have been pivoting in light of COVID-19, and the changes she has seen over the years on women in leadership roles.

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Here’s a Glimpse of What You’ll Hear:

  • Cynthia Cleveland talks about being a CEO coach and how the COVID-19 pandemic has impacted her work and her clients
  • What companies can do to pivot their businesses
  • How Cynthia has helped CEOs make decisions quickly
  • Cynthia talks about her experience as President for Teleflora and Imaginarium and how it is influencing her current work
  • How being part of YPO and women’s groups have helped and guided Cynthia’s career
  • Cynthia shares her thoughts on women in leadership in the current world and what has led to her success in different industries
  • Cynthia talks about working at Vivendi Universal and advancements in music over the years
  • What Cynthia is currently excited about and the current opportunities she sees for businesses
  • The people Cynthia acknowledges for her achievements and success
  • Where to learn more and connect with Cynthia Cleveland

Resources Mentioned:

Sponsor: Rise25

Today’s episode is sponsored by Rise25 Media, where our mission is to connect you with your best referral partners, clients, and strategic partners. We do this through our done for you business podcast solution and content marketing. 

Along with my business partner Dr. Jeremy Weisz, we have over 18 years of experience with B2B podcasting, which is one of the best things you can do for your business and you personally. 

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A podcast is the highest and best use of your time and will save you time by connecting you to higher caliber people to uplevel your network. 

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Check out Rise25 to learn more about our done-for-you lead generation and done-for-you podcast services. 

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Episode Transcript

Intro  0:14  

Welcome to the Revolution, the Smart Business Revolution Podcast, where we asked today’s most successful entrepreneur to share the tools and strategies they use to build relationships and connections to grow their revenue. Now, your host for the revolution, John Corcoran.

John Corcoran  0:40  

Okay, welcome everyone. John Corcoran here, the host of the Smart Business Revolution Podcast. And as you know, each week I get to talk to smart CEOs, founders, entrepreneurs, of all kinds of companies organizations from YPO, EO, Activision Blizzard, lending tree, Open Table, x software, and many more. I’m also the co-founder of Rises25 where we help connect b2b business owners to their ideal prospects. And we’ve got a great guest for you here today. Her name is Cynthia Cleveland. She’s a five time CEO/President overseeing over $4 billion dollars in revenue. And her background is especially relevant for the global pandemic that everyone’s been experiencing over the last five or six months now because she’s an expert in developing, translating, and monetizing IP rights into major global consumer brands. So she’s worked on brands such as Barbie Hot Wheels, Jurassic Park, Myers Briggs assessment, and Imaginarium. So we’re gonna talk all about that, and how she’s helping many of our coaching clients today to pivot and find new revenue sources, which is what could be more relevant than that today. But first, before we hop into that, this message is brought to you by Rise25 Media, our company where we help b2b businesses get clients referrals and strategic partnerships with done for you podcasts and content marketing. And if you’re listening to this right now and you’re curious about starting a podcast, I say it’s one of the best things I’ve ever done. And we specialize with helping b2b businesses with a high client lifetime value to do it profitably, which will guarantee that you do it sustainably and for the long term. So to learn more, go to or you can also email us at [email protected]

All right, Cynthia, so I’m excited to talk to you today about these different clients that you’re working with and how companies are pivoting and, and finding new sources of revenue, identifying and monetizing new areas of the business, which is kind of a real specialty of yours. But first of all, what a crazy time for you to be focused on CEO coaching, you’ve been doing it for a couple of years now. And I’m sure if you know, you’ve had a tremendous amount of experience, you have a lot of mentorship and coaching of different executives and stuff like that. But in terms of full time CEO, coaching, that’s been your focus for the last couple of years, and then this global pandemic hits. So what has it been like, personally for you to be, you know, focused as a CEO coach, and to be, you know, faced with this global pandemic?

Cynthia Cleveland  3:12  

Well, you know, like everybody, when it first hit that, I was shocked, and I had no idea how it would affect this business, if you will, and how it would affect my clients. And I’ve been surprised to see that it hasn’t been as bad as I thought it was going to be in the sense that about 50% of the businesses are actually doing better. You know, I think it feels like the world has fallen. But there are some businesses that are doing better internet based businesses, and a number of businesses actually are doing better than we had hoped. Then, of course, there’s the other part that is not doing more and not doing better immediately. But that’s where I found I have a lot of reward in what I do. Because what if I can help somebody make a pivot, see things differently, because all of a sudden, everybody had to stop and look at everything they were doing, and figure out if it worked. There were some businesses that went to zero, you know, just zero revenue the next day. So whether it’s ranged from helping people understand the PPP process and getting that money in place, refocusing sales forces, I would say that’s been one of the biggest things because if you’ve got a retail bricks and mortar store or restaurant, or a lot of businesses that were selling by left I had one that was door to door where you can imagine nobody’s open their doors at this point. So then it became How can you do you know, it’s always like, I look at it, like life’s a big deck of cards, and you’re playing hand after hand. Okay, now, these are the cards that you’ve been dealt. And I guess I’ve been lucky in that I’ve had that kind of mindset of looking for the opportunity in any sort of a challenge that is just sort of my nature, and I’ve made a lot of changes in my career over time and people have always said to me, Well, how could you do that? How could you go from, you know, being at Mattel and the toy business And all of a sudden running a retailer when you’ve never done that before, but I just never looked at it as that big of a deal I always looked at Okay, well, what can I know now what? So that was something my mother said that I always thought was a good way to look at life in general. Don’t sit and moan about what was but kind of look at now what? And so the minute you start focusing on now what it gets you out of the negative mindset of poor pitiful me. So I would always look at now what’s the opportunity? You know, the Chinese have the yin yang symbol, black and white on one side, black on one side, white on the other. And it means crisis and opportunity. So I’ve always seen that there is always an opportunity in crisis. And so I just tried to stay calm and start looking for what now for my clients.

John Corcoran  5:49  

Yeah, yeah. Are you finding that most companies have got some kind of opportunity that they can pivot into? That’s not too much of a departure? Or have you worked with any clients that have, you know, literally had to completely rip up the script. I’ll give you an example. So one of my recent guests, Andrea Herrera, she had a catering business went from a couple million dollars, three $4 million a year down to 5% of its revenue. And so she says it’s now in hibernation. So she set it aside, basically, and started a completely different business, a really interesting business called box perience, which is delivering these custom boxes as a high end gift for clients to their clients. And it was a really interesting idea, but a really major pivot, you know, some of her background experience in food came into it. But in many ways, it was a wholesale pivot. So what are you seeing in terms of art? Is there where most businesses have something that they can pivot into? Even if the CEO is coming to you and saying, I have no clue what we can do?

Cynthia Cleveland  6:53  

Yes, absolutely. Now, as you said, that was a pretty dramatic one. Sometimes they are that traumatic. And sometimes it actually goes back to thinking about what business you are in? I mentioned briefly, travel is probably one of the most challenging ones out there. And someone in the challenge in the travel incentive business, stood back and said, Okay, well, what business Am I really in? And instead of selling, traveling and sending them to sales incentives, they said, Well, really the business I’m in is the sales incentive business. So in that one by pivoting to a different product, as opposed to travel being the product, that was enough of one. So I think it’s always going back and looking at what your expertise is, there were some folks who were in the product, promotional business, you know, making all the things that trade shows were without trade shows, you can imagine how that business was going. And I know several of them who pivoted and said, Well, I am in the sourcing business. So I can source things really inexpensively. What do people need right now? So a lot of them went into personal protection, the end, the people who did it the quickest, they’ve been the most successful. So it’s a combination of Also, don’t wait, if anybody is waiting to make a change, do not wait one more day, you know, sit yourself down. And even if your business is going well, maybe especially if your business is going well, don’t assume that things aren’t going to change. Because right now one of the opportunities is getting talent has never been better. In some, it’s easy to attract talent, from travel, from hospitality from restaurants. So if you’ve got high performers, and you’re worried about that, and people no longer have that hang up about, well, we have to be in a particular area, you have to live in a particular area, people figured out how to sell from anywhere. So there are lots of do’s and don’ts are things that we thought had to be a certain way that have been challenged. And so both as on the offensive, you can get better people if you’re maybe willing to open up your screen as far as where you’re looking where they’re living, or you can also lose people if you’re not paying attention, because there are people who are realizing that they can come and steal your best people if it’s the right time them.

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