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October 21, 2025 By Annie Gough

Operating Systems Case Study: WEBIT Services, Inc.

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BOS WEBIT (1)

Have you faced struggles with growth plateaus, poor communication, or a misaligned leadership team? Then we have a story that you may relate to. 

We started our Business Operating System (BOS) series with a deep dive into our recommended systems for you to utilize. Now, we’re kicking off our case studies with a very honest look into the realities of implementing an operating system. First up is WEBIT Services, Inc., a computer tech support company based in Naperville, IL. Over the years, WEBIT has been heavily involved in the Small Giants Community, from participating in our Leadership Academy to attending the Summit. Eric Rieger, the company’s founder, is here to tell us their story.

WEBIT’s BOS journey began back in 2016, when their business coach at the time encouraged Eric to read the Great Game of Business book. This sparked an a-ha moment for Eric, as the concept of Open Book Management (OBM) tied in well with their mission and made good business sense. After working with Great Game of Business (GGOB) for several years to get their open book practice off the ground, WEBIT eventually transitioned to their own OBM system.

The Entrepreneurial Operating System (EOS) was later brought in by a former member of the leadership team as a way to keep day-to-day tasks in line with long-term goals. Together, the two systems reinforce WEBIT’s culture of trust and accountability, while also ensuring everyone is on the same page, both with far-reaching goals and daily operations.

WEBIT has seen positive transformations thanks to their implementation of EOS and an open book financial system. In 2016, they had just 9 employees – now, the company is 40 strong. They’ve also jumped from just over a million in revenue to an estimated $7 million this year. As Eric says, they’ve created jobs and opportunities to change people’s lives, and they have also been able to serve more clients and extend the positive impact that they have in the world.

While WEBIT is enjoying the cultural and business impacts of their two chosen systems, neither were completely smooth journeys. Both took trial and error in learning what made the most sense for their company, as well as acknowledging when they could go it alone and when they needed an outsider’s expertise to achieve desirable outcomes. 

WEBIT quote

Eric’s key message? A BOS isn’t a bandage for bad culture - it’s fuel for a good one. Make sure you have your culture and values established, along with a strong leadership team and an overall buy-in mindset. Then, and only then, should you seek out an implementer or expert to help you get going with your chosen BOS. 

Check out our interview with Eric to get a closer look at WEBIT’s journey and lessons learned. 

 

Eric Rieger Skipper Round Headshot-1Interview with Eric Rieger

What is your company's mission?

Our mission is twofold.

First, our daily mission is to seek out businesses that are doing good things for humanity and to amplify their impact by elevating their technology.  

Second, we must become the best possible ESOP (Employee Stock Ownership Plan) to be a beacon of light for other organizations to follow. By doing so, we can contribute to closing the income inequality gap in the United States and set an example for how wealth can be more evenly and ethically distributed across workforces.

 

webit life - WEBIT Services

Describe how your company is structured and how it operates.

We have two divisions: SecureBIT and Upstream Impact. 

SecureBIT is our Managed IT Services & Security division. Upstream Impact is our software development division. We are currently 30% ESOP with the goal of becoming 100% employee-owned by 2030.

We also have a hybrid work environment. 

 

When and why did your company decide to implement new operating systems? What was the culture like previously?

Before these changes, we had a lot of chaos and a lack of accountability throughout the organization. Everyone wanted to do things their own way and it made for unpredictable service delivery and outcomes. 

Once I read The Great Game of Business, the open book management system seemed like a no-brainer and a big missing piece for us. If you teach people how a business operates and how their roles impact the outcomes, you should naturally achieve better results because people are trusted, trained, and empowered to make positive changes.

EOS was brought in by a former member of the leadership team as a way to correlate the day-to-day activities with the long term goals. He had used it at another company and accurately diagnosed that it would give us the structure and focus we were lacking. 

 

Were you at all influenced by another organization or leader on your implementation journey? 

When I decided to pursue OBM, I went into deep dive mode. Being in the Chicago area, I was fortunate enough to be able to see it put into practice at Tasty Catering, which is what convinced me to pull the trigger and bring in the Great Game people to help us implement it. 

ESOP came about as a result of being in the Open Book community and hearing how others had successfully implemented it. 

EOS was brought in by a former leader, and having tried and failed to self-implement, I reached out to EOS and they recommended a local implementor, Paul Detlefs, who helped us get on track. 

Paul is one of the organization’s most senior implementers and he knows the system inside and out. He was able to help us stay focused and true to the EOS process. His experience was a huge value.

WEBIT ESOP event

What key resources, people, organizations, or services were most important to the adoption of this change?

With any change, you have to have buy-in from the leaders first. If they’re bought in, they can lead the shift in mindset and be active in the education process. 

We had a lot of help with coaches and mentors from the Open Book community (GGOB, Zingerman’s) and I’d met several ESOPs through the Small Giants Community. EOS has its own very large community and we’ve met a lot of implementers and practitioners through it.

 

How do these systems help you preserve your culture?

None of these systems can create a good culture out of thin air. They can reinforce a good culture, but you have to be intentional about that and work on it every day. With that being said, OBM is all about transparency, so it helps to build trust, which is a foundational piece of any good culture.

 

How has this change in operations advanced the growth trajectory of your organization?

When we had a total of 9 people on the team I was wearing a lot of hats. Once we started getting the right people in the right seats I was able to focus more on sales. There are 4 levers in a business that have to be in sync to move forward: operations, people, finances, and sales. In order to go from $1 million to $5 million in revenue, the founder has to get things off their plate they aren't good at. Now that we're past $5 million, we have a full-time sales person so I can focus solely on the CEO role.

 

Have these systems had an effect on who is a part of your team?

One of the biggest ongoing challenges has been to get buy-in from new leaders, especially if they are seasoned and used to doing things a certain way. I always reflect back to our recruiting and hiring processes when we have misses there. We’ve made some big mistakes in building our leadership team, and that has gotten us off track with some of these systems. As a result, we’ve had to spend a good amount of time getting back on track with new leaders.

 

What was the most challenging or surprising part of getting your operating system up and running?

Time was a cost for us. Initially we tried doing EOS ourselves, and in my experience, self implementation rarely works. You're trying to put in a new system that you aren't an expert at. It was surprising to others, but not myself, that it failed until we got an implementer to help.

After a year of unsuccessfully trying to self-implement EOS, we hired an implementor. It took another full year to get the system operational, and then a couple more for it to be fully executed down to the department level. 

Transitioning away from GGOB was another challenge. While their structure was helpful to get open book systems up-and-running in our company, ultimately they ended up not being a good long-term fit for us, which is why we switched to our own OBM model.

We've had challenges with our leadership team and structure, so it's been a bumpy ride, but there is more buy-in today than at any time in the past.

 

Some operating systems come with very rigid parameters. Have you tweaked your initial setup at all to better suit your team and your organization?

EOS is structured around one visionary and one integrator; they are pretty strict on that. We broke ranks and divided our leadership team into two groups (6 people each) because we have a software division and an IT services division, and they have different needs and operate at different speeds. 

Our current EOS structure is maintaining a visionary and integrator for each division, and I maintain the visionary role for the entire company. 

The divisions run separate L10s and the two visionaries meet once a month as well. I'm involved with both teams to make sure they stay aligned with the overall company vision. I'm looking at bringing on a general manager to be my integrator because 3 visionaries in a meeting can tend to get way off track. 

 

What advice do you have for other companies looking to set up an operating system?

Hire a coach/implementor. After years of attending EOS and GGOB conferences, as well as talking to lots of business owners, I have yet to meet a company that has self-implemented in a way that I’d call successful. I cannot stress that enough. You aren’t an expert on the system, and you won’t become one through trial and error. 

Also, be prepared for churn. Especially when you introduce transparency and accountability if it wasn’t already there. The good news is that you’ll organically create space for new people who crave these things and will be better fits for what you’re trying to build.

 

Do you see your operating system as an evergreen structure that will help you build a sustainable future for your company, or a temporary bridge to help you advance to the next level?

It's definitely part of our core and in our DNA. Whether it remains evergreen I cannot say, but as long as I'm here and as long as it's delivering results, I would say yes. We don't know the challenges until we run into them, but I see EOS as working at scale. Unless something new comes along that is needed because of AI or other changes to how businesses operate, this will likely be part of our company for a long time.

 

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About Author

Annie Gough

Annie Gough is a writer who is driven by the power of a good story to bring people together. She strives to bring out the human element in business, and provide a platform for people who emulate what it means to be a Small Giant and might inspire others to do the same. She has been a Challenge Detroit Fellow, holds a master's degree in Creative Writing from the University of Stirling, and has worked with a broad range of clients on vibrant marketing and copywriting content.

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