Lakeside Software

Lakeside Software

Monitors IT end-user experience via SysTrack

Overview

Lakeside Software provides Digital Experience Monitoring for large enterprises, focusing on improving IT performance and end-user productivity with its flagship SysTrack. SysTrack collects data from endpoints like computers and servers to measure performance and user experience from the user’s perspective, helping IT teams identify issues, optimize resource use, and boost productivity. The product is offered primarily through subscription licenses, and Lakeside also provides consulting services to help organizations implement SysTrack effectively. What sets Lakeside apart is its emphasis on end-user experience and workspace analytics for enterprise environments, combined with ongoing licensing and advisory services to drive IT cost reductions and better performance. The company’s goal is to help organizations reduce IT costs, improve system performance, and enhance user satisfaction by delivering actionable visibility into IT operations.

About Lakeside Software

Simplify's Rating
Why Lakeside Software is rated
B-
Rated B on Competitive Edge
Rated B on Growth Potential
Rated C on Differentiation

Industries

Data & Analytics

Consulting

Enterprise Software

Company Size

51-200

Company Stage

Growth Equity (Venture Capital)

Total Funding

N/A

Headquarters

Boston, Massachusetts

Founded

1997

Simplify Jobs

Simplify's Take

What believers are saying

  • Mike Schumacher's return as CEO accelerates AI-driven DEX innovation for enterprise scaling.
  • Strengthened leadership team with CFO Brian Curran and CMO Tal Klein enhances execution.
  • EMEA expansion through Oli Giordimaina targets high-demand service desk efficiency and channel growth.

What critics are saying

  • Microsoft Intune's AI analytics displace SysTrack in Fortune 500 firms via Azure integration.
  • NinjaOne's SysTrack acquisition bundles endpoint management with DEX, eroding Lakeside subscriptions.
  • Rapid executive turnover signals instability, deterring enterprise contracts during EMEA expansion.

What makes Lakeside Software unique

  • 27 years of endpoint telemetry data enables proprietary AI models purpose-built for IT.
  • SysTrack Mobile delivers real-time IT insights and natural language querying on mobile devices.
  • Outcome-focused DEX platform addresses IT resource constraints with actionable, measurable productivity improvements.

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Benefits

Remote Work Options

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

0%

2 year growth

0%
SourceSecurity.com
Mar 13th, 2026
Oli Giordimaina joins Lakeside for EMEA growth

Oli Giordimaina joins Lakeside for EMEA growth. 13 Mar 2026 Quick Read Summary is AI-generated, newsdesk-reviewed * Oli Giordimaina joins Lakeside to boost digital experience across EMEA. * Demand rises for AI-driven IT solutions that enhance work productivity. * Lakeside focuses on innovation to address IT-resource pressures with actionable insights. Lakeside Software has announced the appointment of Oli Giordimaina to its executive team, as the company seeks to enhance its innovation and execution throughout the Europe, Middle East, and Africa (EMEA) region. Giordimaina, who is based in Cheshire, UK, brings significant technical and commercial expertise to the role, which aligns with the increasing demand among organisations for improved IT value and predictability. Extensive experience in service desk operations. With a comprehensive background in service desk operations, infrastructure deployment, and product leadership, Giordimaina started his career working on critical systems for companies such as British Aerospace. His professional journey includes key positions at AppSense and Ivanti, where he managed a £100 million product portfolio during times of major change. Most recently, he played a pivotal role in shaping the Digital Employee Experience (DEX) strategy at 1E, just before its acquisition by TeamViewer. The appointment comes at a critical time, as IT departments face increasing pressure to accomplish more with limited resources, while closing the experience gap between consumer and corporate technology. Giordimaina asserts that Lakeside Software is well-equipped to address these challenges, given its advanced endpoint telemetry and action-oriented platform. Addressing growing IT solution demand. Giordimaina stresses that successful AI integration begins with a focus on outcomes rather than algorithms Giordimaina identifies strong opportunities for Lakeside Software across EMEA, largely through its partner ecosystem. In regions like the UK, the emphasis on service desk efficiency and channel delivery is producing a surge in demand for solutions that enhance the employee experience while reducing operational costs. He also highlights the importance of aligning artificial intelligence (AI) innovations with practical value, advocating for a thoughtful approach over a "blind pursuit" of AI. "Employees expect the same seamless experience at work that they get from personal technology - and when IT can't deliver that, frustration builds," said Giordimaina. "Lakeside Software has the data, the platform, and the mindset to close that gap. This isn't about visibility for the sake of it, it's about enabling IT to deliver consistent, measurable outcomes that improve productivity and experience." Focusing on outcome-driven strategies. Giordimaina stresses that successful AI integration begins with a focus on outcomes rather than algorithms. The same principle applies to DEX, which is increasingly becoming a critical performance measure within IT and company leadership. He joins Lakeside Software at a transformative moment, marked by a revitalised leadership team and a commitment to challenging conventional thinking to drive growth and innovation. "The organisations that will succeed with AI are the ones that start with outcomes, not algorithms," he said. "The same applies to DEX, which is no longer a nice-to-have, but is now a critical performance metric across IT and company leadership." Giordimaina cites the firm's innovation-led culture as a major attraction, and he is eager to contribute to Lakeside Software's mission to advance intelligent IT solutions. "This is a company with the right people, the right data, and the right intent," he added. "There's a clear opportunity for Lakeside Software to lead the next phase of intelligent IT. I'm here to help make that happen."

ChannelVision Magazine
May 22nd, 2025
Lakeside Software Hires VP of Global Channels

Lakeside Software appointed Mike Stankowitsch as VP of global channels.

SourceSecurity.com
May 20th, 2025
SysTrack mobile: Real-time IT insights by Lakeside Software

Lakeside Software, the first AI-driven digital employee experience company, announced the SysTrack Mobile Experience, which delivers real-time IT telemetry, natural language querying, and context-aware insights to mobile devices.

PR Newswire
Dec 20th, 2024
Lakeside Software Named Ai Company Of The Year By Cioreview

The company was recognized for its innovation and excellence in leveraging AI to optimize IT operationsBOSTON, Dec. 17, 2024 /PRNewswire/ -- Lakeside Software , the first AI-driven digital employee experience company, has been named AI Company of the Year by CIOReview. Recognized for its innovative use of AI, Lakeside empowers organizations with large, complex IT environments to gain visibility across their entire digital estate, uncovering opportunities to optimize resources.This recognition highlights Lakeside's ability to deliver high-performance solutions that drive tangible value for enterprises. A recent Gartner survey revealed that nearly two-thirds of CIOs have included AI in their innovation plans, yet deployments have grown by only 2-5% in recent years. Part of the challenge is that organizations often struggle to optimize AI for IT.Lakeside's AI purpose-built for IT helps organizations extract actionable insights from IT data to achieve goals such as reducing help desk tickets, enabling self-service for end users, and increasing employee productivity. By enhancing the employee experience, saving time, and optimizing budgets, Lakeside allows businesses to focus resources on core initiatives, not tech disruptions."On behalf of our entire company, I am very honored to receive this award as it recognizes the outstanding effort across our product and engineering teams over the last twelve months," said David Keil, CEO, Lakeside Software

PR Newswire
Oct 15th, 2024
Lakeside Software Named a Leader in ISG's Provider Lens(TM) Evaluation for Digital Employee Experience Solutions 2024 Global

BOSTON, Oct. 15, 2024 /PRNewswire/ - Lakeside Software, the leading IT data intelligence company, has been identified as a Leader by global technology research and advisory firm Information Services Group (ISG) in its 2024 Provider Lens(TM) evaluation for Future of Work Digital Employee Experience (DEX) Solutions.

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