Lakeside Software is a company that helps organizations with large and complex IT environments get visibility across their entire digital estate and see how to do more with less. Pulse 2.0 interviewed Lakeside Software founder and board member Mike Schumacher to learn more about the company.
Mike Schumacher’s Background
What is Mike Schumacher’s background? Schumacher said:
“I’m a software engineer by trade, and early in my career, I worked on ISO standards but found product development more interesting and rewarding. While at Cubix, a hardware company, where I built a ‘skunkworks’ for various software needs, I realized my interest was a software-first approach.”
“In 1997, systems integrators and customers grappled with optimizing compute platforms—how many users could share a system, how to balance resources for peak performance, and how to troubleshoot persistent issues. This challenge led to the creation of Lakeside Software’s SysTrack 1.0, initially focusing on solving these problems for Citrix multi-user platforms. SysTrack was a simple centralized server architecture with black box recording that helped companies maximize server efficiency.”
“Over time, the SysTrack platform expanded to include desktop and notebook environments, incorporating user analytics. As more features were added, SysTrack evolved to serve the needs of what we now know as the Digital Employee Experience (DEX) market. While today’s product offers much broader capabilities, its core mission remains unchanged: helping our customers deliver the best digital user experience at the most cost-effective price.”
Formation Of Lakeside Software
How did the idea for the company come together? Schumacher shared:
“In August 1997, I left my hardware support job to go out on my own. I didn’t know exactly what I was going to build, but I knew it would be something that would appeal to my systems integrator friends. It was just me initially—hence the name Lakeside Software, as I worked out of my den looking out over a local lake. I settled on a software tool to predict the number of users that could share a Citrix server, with instructions on how to balance resources to maximize results. In 1998, Citrix held its first trade show, where SysTrack won Best of Show, and we followed that up with another win at COMDEX. As calls and interest grew, we ramped up from a one-person operation to a small team to meet demand. This “phase 1” ended with a source licensing deal with Citrix, who successfully scaled the product as part of their global offering.”
“The second phase for Lakeside related to understanding people behavior through software usage. It was a desktop/notebook product. In this phase, we patented a new “edge” architecture that harnessed unused resources on monitored devices to analyze data at a very large scale. We re-completely re-architected Lakeside SysTrack to what became known as our Intelligent Edge architecture.”
“As the market began to shift, VMware entered the market, introducing virtualization technology that allowed users to run multiple operating systems simultaneously on a single physical machine. This marked the beginning of widespread adoption of virtualization across the IT industry, transforming how computing resources were utilized.. It enabled us to scale our offering, helping customers maximize resource efficiency across tens of thousands of endpoints. This marked the start of the current Digital Experience Monitoring (DEX) phase of Lakeside’s products.”
Favorite Memory
What has been Schumacher’s favorite memory working for the company so far? Schumacher reflected:
“There are so many great moments, but the ones that really stand out to me are always the people-centered stories. I remember when we had our first big win with a scaled customer—it was a huge bank, and I remember the day the platform went live on 100,000 devices. It eventually grew to 400,000, and that felt like such a milestone.”
“Opening our first international office in London and our R&D center in Ann Arbor brought in a new energy—new environments, new teams, and new designs. It was exciting to see the company grow in so many directions.”
“Winning ‘Best of Show’ awards was always a goal of ours. Bringing the award back to the team was such a highlight—except for that one time when I left the plaque in a Vegas cab! Fortunately, I tracked down that cab in the airport cab stand with 400 other cabs and eventually found the plaque. It was worth the effort!”
Core Products
What are the company’s core products and features? Schumacher explained:
“Lakeside Software is a leading IT data intelligence company focused on delivering a 5-star digital employee experience (DEX). Our flagship product, SysTrack, offers deep insights into IT environments with features such as real-time performance monitoring, AI-driven analytics, root cause analysis, and application optimization. It also enhances remote work support, improves security by giving IT teams visibility into where patches have been made, and tracks user behavior to boost productivity. We help businesses proactively solve issues, right-size resources, and deliver a smooth digital experience. This year, industry analysts Forrester, Gartner, and ISG all have recognized us as leaders in DEX solutions.”
Evolution Of Lakeside Software’s Technology
How has the company’s technology evolved since launching? Schumacher noted:
“Over the years, it’s never really been about the specific technology, but more about the problems we’re solving and having the right people in place. Technology comes and goes—it’s just a set of tools. If you have great people, they’ll pick up new tools and adapt to emerging technologies with ease.”
“We started with a focus on data collection, and while we still leverage that, today we’re looking at how AI and machine learning, alongside modern UI, can take us further. At its core, our mission to optimize the digital employee experience and empower IT to adopt a proactive IT strategy is driven by the people we’ve hired throughout the years at Lakeside. When we hire, we focus on the candidate’s ability to overcome challenges because good people can learn new skills quickly. If you retain great talent, they outlast the pace of tech changes, so it’s all about finding people who can evolve and fit into the culture we’ve built.”
Significant Milestones
What have been some of the company’s most significant milestones? Schumacher cited:
“There have been quite a few significant milestones along the way. One of the earliest was simply having a product that worked at scale—it wasn’t something we took for granted. Winning our first “Best of Show” award was also a huge moment, and every one after that felt just as rewarding because we set a goal and hit it.”
“Securing our first major deal and rolling out our first large-scale implementation were key steps in our growth. One personal highlight was closing a deal with a well-known toy brand when my kids were little—that one felt special because the kids loved the news.”
“Opening our Ann Arbor office in 2014 and our London office in 2012 marked new phases for the company. Since then, we’ve expanded internationally with offices in India, Australia, and Japan, each bringing in new perspectives and opportunities.”
“Another big milestone was the addition of Insight Partners as our investor, giving us the support we needed to scale even further.”
Customer Success Stories
When asking Schumacher about customer success stories, he highlighted:
“In our early days, our early partnership with Citrix was instrumental in driving our initial growth. As we expanded, we had the opportunity to work with a very large automaker who was a challenging but fair customer who took a chance on us as a smaller company. For this client, we successfully integrated CAD and engineering into a unified program, which resulted in securing 25,000 seats across their key subsidiaries.”
“Phase 3 marked a major milestone with a large financial institution that became our anchor client. This partnership allowed us to scale from 100,000 to 400,000 seats, and as a result, we closed several multi-million-dollar deals.”
“Importantly, we maintained strong relationships with customers as they moved on to new roles, continuing to work with them across different organizations.”
Total Addressable Market
What total addressable market (TAM) size is the company pursuing? Schumacher assessed:
“All large enterprises with more than 5,000 employees.”
Differentiation From The Competition
What differentiates the company from its competition? Schumacher affirmed:
“Lakeside has the industry’s best data. With 10,000 data points every 15 seconds and 1,200+ sensors assessing every endpoint, Lakeside’s SysTrack platform collects more telemetry and endpoint performance data than anyone else. Plus, SysTrack retains the granularity and contextuality of the data for 3 years, supporting continuous improvement. Only Lakeside has the data to power AI models that enable IT teams to proactively resolve their most complex issues.”
“This breadth, depth, history, and quality of Lakeside data let you eliminate blind spots. Our SysTrack platform collects data, both on and offline, across enterprise and external networks. You can see the health, performance, and usage of endpoints across your entire IT estate with no gaps in the data or insights.”
“We also have the industry’s best capabilities for root cause analysis. Lakeside accelerates troubleshooting for the most complex technical challenges. Combining historical and real-time data across the IT estate, SysTrack runs automated diagnostics and provides detailed drill-downs for help desk technicians triaging either physical or virtual desktops. Plus, generative AI-powered guidance provides technicians with step-by-step instructions on how to resolve issues based on the specific needs of the environment. We help IT teams move from root cause to resolution faster.”
Future Company Goals
What are some of the company’s future company goals? Schumacher pointed out:
“Looking ahead, I would say that one of our primary goals is to continue scaling the company to better serve our customers, thanks in part to the expertise Insight Partners brought on board when they invested in 2020. There’s still a lot of work to be done in the DEX space, both for our customers and partners.”
“We remain focused on listening to our customers and partners because that’s where we learn about the real-world problems they need to solve. If we understand their challenges, we can create solutions that meet their needs, which naturally drives demand for our products.”
“Our patented product architecture positions us to excel in scalability, mobility, cloud, and privacy. This platform gives us an advantage in delivering the highest-quality data, allowing us to build on this foundation and unlock even more potential for our customers.”
“The standard for a quality computing experience is rapidly rising—people now expect a seamless, consumer-like experience, and IT teams are moving toward a more proactive, trouble-free approach. This shift aligns perfectly with our technology’s ability to improve both user satisfaction and organizational productivity, creating a win-win scenario. Companies want to deliver the best experience at the most effective cost, and that’s what DEX is all about.”
Additional Thoughts
Any other topics you would like to discuss? Schumacher concluded:
“One thing I’d emphasize is the strength of our relationships with customers and partners. It goes far beyond just selling them a product. True success happens when they’re able to use our solutions to effectively solve their business challenges. That’s when we know the relationship is working.”
