News & Content: Member Blog

ITA Spotlight: Flexera

Friday, May 3, 2019   (0 Comments)
Posted by: Kaylin Berg
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Jim Ryan, President and CEO, Flexera @Flexera

Flexera is Chicago’s homegrown software company helping companies save lots of money. You know how you get an electric bill and think, “Why is this so high—did I leave a fan on all month?” We do that for companies, but for their IT spend—for things like licenses and cloud.


In 25 words or less, what is Flexera all about?

Companies spend millions on IT without really knowing where it’s going. Flexera shines a light into this technology black hole, helping customers spend smarter.

What problem do you solve and how do you solve it better than the competition?

We help companies get a handle on their software and hardware investments, understand their operations and figure out how to optimize the chaos that is IT sprawl. We can make sense of a company’s IT spend, saving them millions and millions.

How did you get started?

Flexera grew out of a company started by two Northwestern University computer science students who launched their first product in 1990. This proprietary software tool, InstallShield, quickly became the industry standard for creating installers or software packages. Since then, we’ve grown exponentially through new product developments, mergers and acquisitions, offering a portfolio of solutions that continues to evolve to meet the expanding needs of our customers.

How has your company culture evolved as Flexera has grown?

We’ve grown from a small startup in a basement to a worldwide company with more than 1,300 employees. With that growth, we’ve added talented individuals who help shape our culture. We still like to laugh, have fun and give back to our communities—we just do it bigger now.

What are your primary goals for Flexera?

To help companies realize technology’s power to accelerate their business. We want to help our customers optimize their IT so they can future-proof their companies against their competition and against the threat of obsolescence. And in so doing, future-proof their own careers.

Where do you see Flexera in two years? Five? Ten?

We intend to reshape our category and offer a continually evolving portfolio of solutions that deliver IT insight, spend optimization and agility.

In just a couple of years, we want CIOs saying, “I can’t imagine my life without Flexera—they are critical to my business. By turning insight into action, Flexera has enabled me to take control of and optimize my technology like never before.”

In five years, we’ll be offering even more insight, spend optimization and agility—on an even more global scale.

What’s the No. 1 thing on your to-do list?

Hire, hire, hire! With over 50 positions open at our Chicago-area headquarters and many more open in our offices worldwide, we’re searching for fresh talent to keep up with all the growth we’re seeing in every area of the business.

In your opinion, what are some of the pros and cons of being an Illinois business?

That Midwest mentality: we’re up with the cows and down with the sun. We all work really hard, but we also have good values. We love what we do here every day, but we make time outside of the office to spend with friends, family, participating in community activities or hobbies.

But in today’s tech world, some don’t realize the power that lies outside of Silicon Valley, which can be a catch-22. Being centrally located (an easy commute from downtown and O’Hare) means we can tap into the global talent Chicago attracts.

What are the biggest challenges you face as you scale your business?

Hiring talented people quickly enough.

What’s the biggest obstacle you’ve faced as an organization, and how did you overcome it?

It’s always a challenge integrating acquired companies into our teams. That’s never an easy thing to do, especially as a global company. But our People department and our Site Leaders have done a spectacular job ensuring seamless integration of talented employees on all levels.

As we grow and scale, we try to keep close to our employees to hear what’s on their minds. We have listening sessions, all-hands events and other communication channels, but we rely most on our leaders to carry the message.

What motivates your employees to come to work every day?

Autonomy: the chance to dive in and get going. We’re a growing, changing company. We have a lot to do and there’s no time to micromanage. If you like owning a project or role that will make a big impact, we empower you to do your thing.

Candor: We “hit people right between the eyes” and Flexerans always know where they and the company stand – no surprises.

Purpose: Managers are encouraged to motivate employees by figuring out what makes them tick and aligning their personal and professional goals with their role at Flexera. We’re all different in our needs and wants, and there’s no one-size-fits-all mentality here.

Why does Flexera call Chicago its home?

Flexera changed its global HQ from Silicon Valley in 2008 and we haven’t looked back.

What was the ‘aha’ moment when you realized Flexera made it?

I’ve never had that moment and I hope I never do. We not even scratched the surface on how great we can be and, as a result, we not made it.

What do you do to encourage constant growth and change for your employees?

I constantly remind people that they have my explicit permission to Initiate and Agitate every day and, in doing so, they will find opportunities for growth. I believe in the adage “80% of responsibility is taken not given.”

How does Flexera interact with the Chicago community?

As “Give Back” is one of our core values, we’re involved with a number of local organizations such as Girls in the Game and Habitat for Humanity.

What is the top reason employees would say they love working for Flexera?

People work here, well, for the people. Our people stay with us for the camaraderie of smart, passionate teams made up of professionals who actually like working together. We have so many people that have been here for a decade or two. People generally don’t hang around if there are a bunch of, well you know the word, working at the company.

Plus, we play a critical part in the hottest tech categories: Cloud. Internet of Things. Security. SaaS. Data. That’s fun to work on.

What makes Flexera stand out?

Our portfolio. We’re a one-stop shop for IT needs. From on-premises, SAM, SaaS, cloud, all of our products are developed for quick and seamless implementation.

What is the one thing Flexera cannot live without?

Our passionate employees – without them, we wouldn’t have nearly half of the success we’ve seen.

What’s the coolest perk Flexera’s office has?

Depends on who you ask, but unlimited vacation is often cited as a pretty sweet perk.

This one is all you… anything else you want to tell us?

 A global software company approaching a half billion in revenue (and growing) that is headquartered in Illinois. An indisputable ‘Tech Unicorn’. If you live in Illinois and work in technology, you really should get to know us!

Get in touch

20 N. Wacker Drive, Suite 1200
Chicago, IL 60606

PH: 1.312.435.2805