LeadingIT
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Chicago, IL · Website
★ 5.0 (189 reviews across 1 source, 4 locations) · 4 claimed certifications
Chicago MSP and cybersecurity provider. 3x Inc. 5000. Expertise.com listed.
Source data last changed: October 26, 2026
Our Assessment
LeadingIT currently ranks #7 of 102 active, scored IT providers in our Chicago-area database, with a Default Fit Score of 38.4% — 18.6 points above the pool average of 19.8%. Scores recompute nightly from public data under our published methodology; no provider pays to be ranked.
Its public review footprint spans 189 client reviews averaging 5.0/5: Google 5.0/5 (189 reviews). Employees rate the firm Indeed 4.2/5 (6 reviews); Glassdoor 2.7/5 (28 reviews) — employee sentiment feeds the score because it predicts service stability.
On security we record 4 claimed certifications — none of it carries third-party documentation, so the security score is capped at the claims maximum. We track 4 office locations for it in the Chicago area, from Google Places. 1 notable company event (awards, acquisitions, milestones) appear in its record below.
Public Criteria Attainment
Scored on 4 public criteria. Sign in to see all 10.
LeadingIT Reviews by Source
Employee Role Analysis
Proactive vs. reactive employee role mix based on workforce composition data.
1 proactive, 8 reactive
Security & Compliance
Strengths
- + 5.0 avg client rating — Google
- + 189 client reviews across 1 platform — Google
- + Strong recent reviews (5.0 avg, last 12 months) — Google
- + Flexible contracts (month-to-month, easy exit) — vendor feed
- + Listed on 4 industry directories — Clutch, Indeed, Manifest, Glassdoor
- + 16+ years in business — vendor website (claimed)
- + Serves Healthcare, Finance, Legal, Manufacturing +7 more verticals — vendor website (claimed)
- + Offers Fully Managed, Co-Managed, vCIO, Help Desk, 24/7 Monitoring, Unlimited Support services — vendor website (claimed)
Weaknesses
- - Client reviews on a single platform only — Google
- - Below-average employee reviews (3.0) — Indeed, Glassdoor
- - Security certifications are the firm's own claim — no third-party documentation on file
- - Heavily reactive support model (89% reactive roles) — Apollo
Notable Events
Company milestones and achievements
LeadingIT founded in Chicagoland
LeadingIT was founded by Stephen Taylor as a managed IT services and cybersecurity provider serving businesses of 25-250 end users across Northern Illinois, Southern Wisconsin, and Northwestern Indiana.
Jan 1, 2010
Recent Activity
Data changes from the last 90 days
Oct 17, 2026
Oct 15, 2026
Oct 14, 2026
Oct 11, 2026
Sep 26, 2026
Frequently Asked Questions
How is LeadingIT rated by clients?
LeadingIT averages 5.0/5 across 189 public client reviews from Google. We aggregate these nightly and weight them with Bayesian averaging so a handful of reviews can't dominate the score.
Does LeadingIT hold security certifications?
LeadingIT lists 4 security frameworks: 4 claimed certifications. None carries third-party documentation — a named issuer's document or evidence hosted off the firm's own domain — so these count as claims and are capped in the score. The Security & Compliance section above labels each one.
Where is LeadingIT located?
LeadingIT is based in Chicago, IL and operates 4 office locations we track. Our rankings cover IT providers serving the Chicago metro area.
How does LeadingIT compare to other Chicago MSPs?
LeadingIT ranks #7 of 102 scored providers in our database under default weights. Use the comparison links on this page for side-by-side breakdowns, or run a custom evaluation to weight all 10 criteria for your own priorities.
Compare LeadingIT
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For LeadingIT: show off your ranking
This firm has earned a Top 10 badge in our current rankings. If you work at LeadingIT, you can embed it on your website — it links back to this profile and updates automatically as rankings change.
<a href="https://itsupportchicago.net/vendors/leadingit?utm_source=badge&utm_medium=embed" title="LeadingIT on IT Support Chicago"><img src="https://itsupportchicago.net/api/badge/leadingit" alt="LeadingIT — Top 10 on IT Support Chicago (2026)" width="220" height="64" loading="lazy"></a>
Usage: link only to your own profile page, keep the current tier, and remove the badge if delisted. Google's guidelines recommend adding rel="nofollow" to embedded badges — that's fine with us. Full terms: itsupportchicago.net/badge.
Source data last changed: 10/26/2026. Report an issue