The Constant Evolution of Companies, with Flexera CEO Jim Ryan


Or listen in your favorite podcast app

Apple Podcasts  /  Google Podcasts Stitcher

Throughout the last twenty-plus years, Jim Ryan has seen his company, Flexera, change and grow in exciting ways. And he’s been able to grow with the company along the way. Today, Jim is the CEO of Flexera, and he joins IT Visionaries to discuss his journey. Plus he dives into how members of the C-suite can find ways to be more efficient, cost-effective, and build out long-lasting companies.

Best Advice: “You can’t make everybody happy. Just be yourself and be authentic.

What Jim is most excited about for the future of technology: “It’s the great unknown. It’s going to be fascinating to see what the next generation will come up with.”  

Key Takeaways:

  • How CIOs have evolved
  • Working with the C-suite and identifying ways they can improve business
  • What it means to partner with members of the C-suite

Jim’s origin story

Jim fell into the tech industry through dumb luck. He originally thought he would go to law school but when his family fell on hard times and he could no longer afford to pursue a law degree, Jim switched to studying technology and took a job at IBM.

The early days of Flexera

Back in 1998, when Jim first joined Flexera (it was not called that then), things were completely different. And the company has continued to change throughout the more than 20 years that Jim has been there. Today, Flexera offers solutions to software and IoT companies.

“We seem to shed our skin every five years. There’s always a different challenge and always a different value proposition.”

How has the role of CIO evolved

According to Jim, the role of CIO has changed dramatically, and it’s been a rapid change. A decade ago the CIO and the IT department had a tremendous amount of power. The IT department controlled what you could have on your computer and what you could do on it. It was a tightly-controlled environment. Now, Jim explains, there has been a sea change in how things are done. There are often no gatekeepers and IT has gone from commanding and controlling, to being a partner and enabler to help the business go forward. But even though IT is helping enable all manner of processes for the business, Jim says that the CIO and the IT department still need to have a certain amount of control in order to protect the business.  

Jim also says that the conversations CIOs have and their fears have shifted in recent years. Contending with the cloud and protecting the business from bugs and hacks that come in through the cloud are currently the biggest topics of conversation.

Who does Flexera work with?

Flexera has thousands of customers, and Jim says there is no one type of CIO or CFO that they deal with. But the ones that do best are internally nicknamed Thomas. And Thomas is defined as a trailblazer, risk-taker, and not content with the status quo. Thomas wants to do great things and expand his career. Those are the attributes of the type of CIOs and CFOs that succeed using Flexera. They look at their job as being an enabler to help the business grow and flourish because when the business grows, an individual’s career can grow as well. Anyone who wants to digitally transform their company will do well.

“People are afraid that they are becoming obsolete themselves, or the technology that they’re running are going to become obsolete or that the very company that they work for are going to become obsolete.”

Where can people improve?

For most CIOs, 60% of the budget goes to hardware, software and cloud compute and a lot of money can be wasted without realizing it. Jim says that software is a lot like electricity. Electricity runs and powers everything, but we can’t see or feel it, and we have no idea how much it really costs. Software is similar. It’s an intangible, virtual asset that’s difficult to touch and feel. Jim explains that Flexera’s value prop is that you can’t measure, protect and save the things you don’t know exist. So they shine a light on all those systems and make sure everything is running right and clients are not overpaying.

“Many companies we deal with don’t have a single or multiple software meters or utility meters running to keep track of their software. And that’s really what Flexera does.” 

“Ironically, the more cloud computing there is and the easier access that we give employees to this technology, that actually makes the job of the CIO, the CFO, and the CEO even harder to make sure that we’re not overspending.”

Partnering with the CFO and other C-level execs

A CIO has to become a mini CFO because they are controlling a large portion of a company’s budget. Regardless of what title you’re carrying, you have to be able to speak finance, lockdown budgets, and look into the future thinking about how you’re going to fund things. Everyone in the C-suite must also be excellent communicators because so much of what they’re doing these days is change management. 

When Jim works with CIOs, CFOs, or anyone else in the C-suite, often the first thing that needs to happen is a conversation about the overarching business plan. Only when you understand that can you go about coming up with solutions to things like transitioning to the cloud and enabling digital transformations. 

“You’ve got to spend money to maintain and duct tape your legacy systems together, but also keep pace, fund and pay and budget for some of this leading-edge stuff in the cloud and SAS, to make sure that your business is maintaining its competitive posture.” 

“Change management requires terrific communication skills, which is perhaps something that wasn’t required 10 years ago. Good communication skills are key.”

What’s next for Flexera

Jim doesn’t like that people call Flexera the best-kept secret in the industry. He and his team are working to make sure that Flexera is loud about what it’s got going on. Jim believes that Flexera is the industry best in providing insight to CIOs and then guiding them to take action, and that’s a message they are trying to amplify 

“Our areas of focus are on providing the best insights into a company’s technology landscape, providing the best spend optimization capabilities and then the layers of automation to go and turn those insights into action.”

Employee experience at Flexera

At Flexera, success centers around six things: candor, passion, keep score/be accountable, be professional, celebrate success, be good corporate citizens.


Love this? Share it with your friends!


Subscribe in your favorite podcast app.


Flexera CEO Jim Ryan joins IT Visionaries to explain how he works with C-level executives to make their businesses more efficient.

The Mission Daily

Our Podcasts