Following the Money With Jim Ryan, President and CEO of Flexera

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“I like the word ‘framework’…the right operating framework allows people to innovate and thrive, but also has the check and balances necessary to make sure everybody is coordinated.”

For more than twenty years, Jim Ryan has helped shepherd Flexera, a global software company, into massive success. How has he managed to help keep core values in the midst of expansion? He stops by Business X factors to talk about scaling with integrity, following the money, and why bureaucracy might not be a dirty word, after all.

Key Insights

How can bureaucracy be helpful? 

We’ve been conditioned to hate the idea of a bureaucracy. Red tape, slow response times… we think that a place without bureaucracy is a place where things get done. But Jim reminds us that bureaucracies have a place in business, and they can be systems that protect everyone. 

“You have to put more process in for controls to keep your tax situation and everything on the up and up. Some people come from a smaller company and say, ‘You guys are just bureaucratic and cumbersome,’ and that’s not why any of this exists. No one wants to be bureaucratic, but as you get bigger, the liabilities and the cost of being off by a percent or two gets magnified.”

How do you find that scaling sweet spot?

Every business wants to grow. But the trick is to find the right timing. Go too fast, and you burn out. Go too slow, and you lose momentum. 

“You don’t want too much, you don’t want too little. You want it just right. I think our ability to scale and to grow and be successful over a long period of time is a direct byproduct of us assessing when it’s too hot or too cold.”

What does it mean to follow the money? 

If you follow the money, you’ll find the customers. You’ll find the problems that need solving. You’ll find the place where you can provide the best service. But, importantly, you’ll find the most important parts of your business and where money might be saved or invested better. Flexera has been able to follow the money to help customers succeed for a century

 “We’ve carved out a space that allows us to find out everything that’s being used, pull it back and contextualize it. And then we run algorithms across it based on our knowledge of how these things are licensed and entitled to help get great outcomes for our customers. It’s a massive problem. It’s measured in the trillions of dollars. And if we can help just save just a few points on the trillions of dollars that are being spent in this area, those are big outcomes. And it’s ultimately what helps us as a company survive over a quarter century.”

About the Guest:

Jim Ryan is President and CEO of Flexera, a global software company. He is obsessed with candor, passion, professionalism, keeping score, celebrating success and giving back. He is known for driving change, developing talent and encouraging transparency, leading to Flexera consistently being named a “top workplace”.

He guides our company as its chief executive and provides strategic vision as we move forward. Jim has been with the company since 1998, spending seven of his years overseas running our international operations. Prior to becoming CEO in 2016, Jim was Flexera’s Chief Operating Officer.

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Episode 48