About Datastrive
Two decades of trusted IT support for Chicagoland businesses. A senior team of engineers, vCIOs, and security specialists — based in Chicago, focused on the city, and built around the kind of long-term relationships generic MSPs aren’t structured for.
- ✓ 20+ years in Chicago
- ✓ Senior engineering team
- ✓ Vendor-neutral guidance
- ✓ Long-tenure client relationships
Get in Touch
A 30-minute conversation with a Chicago-based senior engineer about your IT environment.
20+ Years of Building Real Chicago IT Relationships
Datastrive started as a small Chicago IT firm focused on doing IT support the way it should be done — senior engineers, fixed-price agreements, predictable service, and relationships that last decades, not contract terms. Twenty years later, we’re still in Chicago, still independently owned, and still delivering the same kind of senior engineering and steady relationships that built the firm. We’ve grown — but not in the direction of becoming another generic national MSP. We’re still local, still senior, still focused on Chicagoland businesses.
Six Things That Make Datastrive Different
These aren’t marketing phrases — they’re the operational decisions that shape every engagement.
Chicago-Based, Always
Our office is on Montrose. Every engineer is based locally. We don’t outsource helpdesk to other timezones, and we don’t pretend remote-only is the same as local presence.
Learn more →Senior Engineering Team
Our average engineer has 12+ years of IT experience. We don’t deploy junior staff on client accounts; senior engineers handle every engagement with peer-level conversations.
Learn more →Vendor-Neutral
We don’t resell hardware or software with commission incentives. Recommendations are based on fit, not financial relationships. Vendor-neutral guidance has been our practice for 20+ years.
Learn more →Long-Tenure Relationships
Most of our clients have been with us for 5+ years; many for 10+. The same is true for our engineers — long tenure on both sides means deep institutional knowledge.
Learn more →Compliance-Aware Engineering
HIPAA, PCI DSS, FFIEC, SOC 2, NERC CIP, CJIS, ITAR, CMMC — compliance isn’t an add-on at Datastrive. It’s built into how we scope and deliver.
Learn more →Predictable Pricing
Fixed monthly fees, transparent scope, no hourly surprises. Most clients get one predictable bill that doesn’t balloon when something goes wrong — that’s the entire point of managed IT done right.
Learn more →One Hire vs. an Entire Bench.
Hiring a single in-house IT person costs roughly the same as a full Datastrive managed support agreement — but a single person can’t cover 24/7, can’t be a senior network engineer and a cybersecurity specialist and a vCIO at the same time, and goes on vacation. Managed IT support gives you depth, redundancy, and predictable cost without the recruiting risk.
- Compliance-Aware Engineering. CIS Controls, HIPAA, PCI DSS, and cyber insurance.
- Predictable Flat-Rate Pricing. One monthly invoice covers everything.
- Proactive, Not Reactive. Most issues resolved before your team notices.
- Local Chicago-Based Team. Onsite at your office, not on the other side of a phone tree.
Managed IT Support Across Chicagoland
Frequently Asked Questions
Common questions about Datastrive — who we are, who we serve, and how we work.
How long has Datastrive been in business?
Where is Datastrive based?
What size businesses do you support?
What industries do you specialize in?
Are you certified or accredited?
How do we get started?
Ready to Talk to a Senior Chicago Engineer?
Book a free 30-minute conversation. We’ll review your IT environment, talk through what you’re trying to accomplish, and quote a fixed-fee engagement if it’s a fit — no obligation.
- ✓ 30-minute conversation with senior engineer
- ✓ IT environment review
- ✓ Fixed-price proposal sized to your business
- ✓ Response within 1 business hour
Talk to Our Team
A quick conversation about your business and IT environment.