LeadingIT

What LeadingIT does

LeadingIT is a Chicago-based managed IT services provider (MSP) founded in 2010 that delivers fully outsourced and co-managed IT support to small and mid-sized businesses with 25 to 250 users across the Chicagoland and southern Wisconsin markets. Its core offering is a flat-rate monthly managed IT subscription that bundles unlimited help desk support, 24/7 monitoring, cybersecurity, data backup and recovery, disaster recovery planning, vCIO strategic advisory, and regulatory compliance services (HIPAA, PCI DSS, FTC Safeguards, FERPA, COPPA, NIST/CJIS for municipalities). The technology stack is a conventional managed services platform with 24/7 monitoring and remote threat detection infrastructure, complemented by a proprietary CyberSCORE Assessment tool used for security evaluations and lead generation, and coordinated vendor relationships for VoIP phone systems and structured cabling.

The company operates from four physical offices (Chicago headquarters, Woodstock, Manteno, and Naperville) and employs 35+ team members serving 150+ active clients managing 3,500+ endpoints. Go-to-market is sales-led with inside sales, online booking, free consultations, and a referral program. Revenue is generated primarily through recurring monthly subscriptions on managed IT and Hardware-as-a-Service (HaaS) leases, supplemented by project-based professional services for cloud migrations, office moves, and network deployments. The company addresses a vertically diverse customer base including manufacturing, municipalities, nonprofits, private schools, law firms, banks, CPAs, distribution/logistics, fire protection districts, and AEC firms.

Strategic positioning emphasizes local presence with on-site response SLAs (within 1 hour), 15-minute critical-issue response, a 98% positive ticket feedback rate, a 4.9-star Google rating across 150+ reviews, and a 100-day Unbeatable Guarantee offering a 3-month refund. The company has earned external recognition including Inc. 5000 placement, CRN MSP 500 (2024), MSSP Alert Top 250, Expertise.com Best Managed IT Service Providers in Chicago 2025, and the APA Bell Seal for Workplace Mental Health at Silver level (2026). Leadership is centered on founder and CEO Stephen Taylor. No public funding, M&A, or investor backing is disclosed in the input data.

Name

LeadingIT

Legal name

LeadingIT

Website

https://goleadingit.com

Company type

Private

Founded year

2010

Operating status

Operating

Headcount range

11–50 employees

Short description

LeadingIT is a Chicago-based managed IT services provider founded in 2010, offering flat-rate managed IT, cybersecurity, compliance, and vCIO services to small and mid-sized businesses with 25-250 users across Chicagoland and southern Wisconsin.

Ownership category

akta.pro rank

Product category

Managed IT Services

NAICS

Computer Systems Design and Related Services (54151), Computing Infrastructure Providers, Data Processing, Web Hosting, and Related Services (51821), Business Service Centers (56143)

SIC

Services-Computer Programming, Data Processing, Etc. (7370), Services-Computer Integrated Systems Design (7373)

akta.pro primary industry

Helpdesk & End-User Support Services (BPAEABAB)

akta.pro secondary industries

ITSM Managed Services (Run/Operate/Optimize) (BPAEAJAN), Workplace Service Desk & Onsite Support (Deskside/Field Services, VIP Support) (BPAEAIAJ), Service Desk & ITSM Outsourcing (BPAEAMAF), IT Asset Lifecycle Services (Procure-to-Retire) (BPAEAOAF)

Keywords

• Managed IT services
• IT help desk
• Cybersecurity services
• IT compliance services
• Cloud computing support

Headquarters

HQ city

Chicago

HQ country

United States

HQ region

North America

Offices4 records

Markets served

GTM type

B2B

Offering type

Services

Cost components

Personnel, Technology or R&D, Operations, Marketing or Sales, Infrastructure

Revenue model

1. Managed IT Services: Flat-rate monthly managed IT services providing unlimited support, 24/7 monitoring, cybersecurity, data backup, and compliance services. One predictable price with no surprise bills.
2. Hardware as a Service (HaaS): Flexible equipment leasing model allowing businesses to scale technology needs while sticking to budget. Manages equipment procurement and lifecycle.
3. Professional Services: Additional services including cloud migrations, office moves, server and networking projects charged separately from base subscription.

Pricing tiers

Go-to-market motion3 records

Distribution channels3 records

Marketing channels6 records

Core offering

LeadingIT provides fully managed IT services to small and mid-sized businesses (25–250 users) across the Chicagoland and southern Wisconsin region. Its core offering is a flat-rate monthly subscription bundling unlimited IT help desk support, 24/7 monitoring and threat detection, layered cybersecurity, automated data backup and recovery, disaster recovery planning, and IT compliance services. The portfolio also extends to co-managed IT for organizations with internal IT staff, hardware-as-a-service procurement, structured cabling, VoIP coordination, vCIO strategic leadership, and managed website services.

Product overview

LeadingIT is a managed IT services provider offering a unified portfolio of technology services designed for growing organizations with 25 to 250 users in the Chicago area. The core offering is fully managed IT support combining cybersecurity, IT help desk, data backup and recovery, and compliance services. The product portfolio includes Co-Managed IT (for businesses with existing internal IT teams), dedicated Cybersecurity services, IT Help Desk with guaranteed response times, Data Backup & Disaster Recovery, Hardware as a Service (HaaS), vCIO strategic leadership, and specialized VoIP Phone Systems. Compliance services cover HIPAA, PCI DSS, FTC, and general IT compliance requirements. Add-on services include Managed Websites and the CyberSCORE Assessment for security evaluation. The company differentiates through unlimited support pricing, local dedicated technicians, and an unbeatable guarantee program.

Differentiator

Problem solved

Functional benefit

Products and services

• Managed IT Services (Unlimited Support) Flat-rate monthly subscription providing unlimited IT help desk support, 24/7 monitoring, cybersecurity, data backup, and compliance services to small and mid-sized businesses with 25–250 users across Chicagoland and southern Wisconsin.
• Co-Managed IT Flexible IT support model that works alongside internal IT teams to fill gaps in cybersecurity, after-hours monitoring, compliance, infrastructure projects, or staff transitions, providing access to enterprise-grade tools and specialists.
• Outsourced IT Support Full outsourcing of IT support functions for businesses that prefer not to maintain internal IT staff.
• Cybersecurity Services Multi-layered security services including endpoint detection and response, network management and security monitoring, email security, security awareness training, and 24/7 threat detection to protect against ransomware, phishing, and data breaches.
• IT Help Desk Responsive technical support with critical issues receiving response within 15 minutes through remote monitoring and on-site assistance within 1 hour for urgent problems, covering password resets, hardware troubleshooting, and network support.
• Data Backup & Recovery Automated backup and recovery services for email, file systems, cloud services platforms, and line-of-business applications, ensuring critical information is securely stored and quickly recoverable.
• Disaster Recovery Planning Strategic planning services to ensure business continuity in case of catastrophic IT failures or disasters.
• Hardware as a Service (HaaS) Flexible equipment scaling model allowing businesses to maintain up-to-date office technology with supported hardware while managing budgets.
• Structured Cabling Coordination of structured cabling projects from assessment and design through installation and testing with vetted vendors, managing projects for new office buildouts or upgrades.
• VoIP Phone Systems Management of VoIP phone system selection, deployment, and ongoing support, coordinating implementation through vendor partners and handling network integration.
• vCIO (Virtual Chief Information Officer) Strategic technology leadership providing guidance to help businesses navigate technology challenges and optimize IT infrastructure.
• Managed Websites Website management services as part of the comprehensive managed IT offerings.
• IT Compliance General IT compliance services helping businesses meet industry-specific regulatory standards from data security to audit preparation.
• HIPAA Compliance IT compliance services helping healthcare organizations meet HIPAA requirements and maintain proper safeguards for protected health information.
• PCI Compliance Compliance support for businesses processing payment card data to meet PCI DSS requirements.
• FTC Compliance FTC Safeguards Rule compliance services for financial services, accounting firms, and other covered entities.
• CyberSCORE Assessment Free confidential cybersecurity assessment that identifies inefficiencies and vulnerabilities in IT infrastructure, providing organizations with a report and Security Action Plan.

Quantifiable outcome

• Response within 15 minutes for critical issues through remote monitoring
• +3 more outcomes

Named customers3 records

Segments12 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature3 records

Partnerships

One partnership is on record.

• VoIP Vendor PartnerssupportingTechnology or IntegrationLeadingIT coordinates VoIP phone system implementation through trusted vendor partners and handles integration with existing network infrastructure, ensuring call quality and reliability.

Scale indicators9 records

Recent moves6 records

Expansion highlights6 records

Direct peers

• US Signal: US Signal is a Midwest managed services, cloud hosting, and data protection provider serving SMB and mid-market customers with managed IT, backup, and DR offerings. Comparable geographic roots, service mix, and customer profile.
• Netgain Technology: Netgain is a Midwest-rooted (Minneapolis) managed IT, cloud, and cybersecurity provider serving SMB and mid-market clients with flat-rate managed services. Direct regional peer with similar size, customer profile, and vertical emphasis on regulated industries like accounting and healthcare.
• Sentinel Technologies: Sentinel Technologies is an Illinois-based IT services firm offering managed IT, cybersecurity, cloud, and structured cabling to mid-market clients in the Midwest. Geographic overlap and similar service portfolio make it a close Chicago-area peer.
• Ntiva: Ntiva is a mid-market focused managed IT, cybersecurity, and cloud services provider with a comparable SMB/mid-market customer profile, flat-rate managed services model, and emphasis on help desk, cybersecurity, and compliance. It is a like-for-like competitor to LeadingIT at a larger scale.
• Switchfast Technologies: Switchfast is a Chicago-based managed IT and cybersecurity provider serving SMBs with flat-rate managed services, help desk, and compliance offerings. The closest direct local peer in geography, size, and product positioning.
• Dataprise: Dataprise is a U.S. managed IT and cybersecurity provider serving mid-market organizations with managed services, help desk, cloud, and compliance offerings. Highly comparable in product mix (managed IT + security), customer size (SMB to mid-market), and subscription pricing model.

Others

• ConnectWise: ConnectWise is a leading software platform provider for MSPs (PSA, RMM, cybersecurity). While not a direct competitor, it is the primary enabling technology vendor for MSPs of LeadingIT's size and shape.

Broad incumbents

• CDW (Managed Services): CDW is a large multi-billion-dollar technology solutions provider offering managed services, cybersecurity, and hardware-as-a-service to mid-market and enterprise. Its scale and procurement advantages make it an incumbent competitor, especially for larger mid-market prospects.
• Rackspace Technology: Rackspace is a global managed cloud and IT services provider with managed security, help desk, and cloud migrations. Overlaps with LeadingIT's managed IT, cybersecurity, and cloud migration offerings but typically serves larger enterprises.
• Kyndryl: Kyndryl is a large global IT infrastructure services provider offering managed services, ITSM, and digital workplace solutions. While not directly competing at the 25–250 user tier, it represents the national/global incumbent that LeadingIT's mid-market customers may be courted by or compared against.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks5 records

Key highlights7 records

Customer concentration

• Xx.com/GoLeadingIT
• Facebookfacebook.com/leadingit
• LinkedInlinkedin.com/company/goleadingit

Compliance6 records

Revenue estimate

Valuation estimate

Number of profiles

Profiles1 record

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about LeadingIT