Managed Cloud · Chicago Metro

Managed Cloud Services in Chicago

From migration to ongoing management — your cloud, simplified. Microsoft 365, Google Workspace, hybrid cloud, and tailored cloud solutions for Chicago businesses ready to move beyond on-prem.

  • ✓ Microsoft 365 & Google Workspace
  • ✓ Hybrid cloud expertise
  • ✓ Migration without downtime
  • ✓ Ongoing security & cost optimization
Get a Free Cloud Assessment1-773-863-3868

Get a Free Cloud Assessment

A 30-minute review of your current setup and what cloud could (or shouldn’t) replace.

🔒 Your information is private. We respond within 1 business hour.

20+
Years serving Chicago businesses
< 1 hr
Average helpdesk response time
24/7
US-based monitoring & support
100%
Chicago-based team
Cloud, Done Right

The Cloud That Actually Saves You Money and Headcount

Most "cloud projects" overshoot — companies move workloads to the cloud that should have stayed on-prem, or stay on-prem when they’d save money in the cloud. Our managed cloud services start with the question that gets skipped: what should actually run where? Then we plan the migration, manage the environment, and keep the bill predictable.

Cloud Services

Strategy, Migration, and Ongoing Cloud Management

Six core cloud capabilities — for businesses moving to the cloud, already in the cloud, or running hybrid environments.

Cloud Solutions Strategy

Tailored cloud strategy for Chicago businesses — what to migrate, what to keep on-prem, and what hybrid looks like for your environment.

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Microsoft 365

M365 deployment, migration, license management, security configuration, and ongoing support across Exchange, SharePoint, Teams, and OneDrive.

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Google Workspace

Google Workspace migration, configuration, and management — for businesses preferring Google’s collaboration platform over Microsoft’s.

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Cloud Migration

Plan and execute cloud migrations without downtime — workload analysis, cutover strategy, and post-migration validation.

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Cloud Security

Cloud-native security: identity controls, conditional access, MDR for M365, data loss prevention, and compliance configuration.

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Hybrid Cloud

Hybrid environments where on-prem and cloud workloads coexist — networking, identity, backup, and security across both worlds.

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Why Datastrive

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.
24/7

Proactive monitoring & response

Industries We Support
ManufacturingHealthcareFinancial ServicesLegalProfessional ServicesNon-Profit
Book a Free IT Health Check
How It Works

Switching IT Providers Shouldn't Be Painful

Three steps to a calmer environment. Most onboardings are completed inside two weeks.

1

Schedule Your IT Health Check

A 30-minute call to understand your business, your software, and the IT pain points actually slowing you down.

2

Onsite Discovery

We visit your office to inventory your network, workstations, and security setup — everything we need to build an accurate proposal.

3

Tailored Proposal

You get a clear, fixed-price proposal mapped to your team size, your software, and your goals — no surprise add-ons.

Local Coverage

Managed IT Support Across Chicagoland

ChicagoNapervilleSchaumburgAuroraRosemontOak BrookElk Grove VillageSkokieDowners Grove
FAQ

Frequently Asked Questions

Common questions about managed cloud services and what cloud strategy looks like for a Chicago business.

What managed cloud services do you offer?
Cloud strategy and assessment, migration, ongoing management of M365 and Google Workspace, hybrid cloud architecture, and cloud-native security. All available bundled into managed IT support or as standalone engagements.
Microsoft 365 vs Google Workspace — which is right for us?
Most Chicago businesses (especially those with deep Office/Outlook habits) end up on Microsoft 365 for compatibility and feature depth. Google Workspace tends to fit teams that are heavily collaborative, prefer simpler admin, or already use Google’s ecosystem. We recommend based on your team’s actual workflows after a discovery call.
How does cloud migration actually work?
Discovery and assessment first (what you have, what depends on what), then a phased migration plan that preserves access and data integrity. Most migrations finish in 4-12 weeks depending on scope. We don’t do "lift and shift" without thinking — workloads that don’t belong in the cloud stay where they belong.
What about cloud security?
Cloud security is its own discipline — identity, conditional access, data loss prevention, MDR for the cloud platform, and configuration hardening. We bundle cloud security into managed cloud engagements and provide standalone security reviews for businesses that already migrated without it.
Can we do hybrid cloud (on-prem + cloud)?
Yes — this is most Chicago businesses, actually. Production servers stay on-prem, M365 in the cloud, certain workloads (like analytics or backup) in cloud-only. Hybrid done right is more cost-effective than going all-cloud or all-on-prem.
What does managed cloud cost?
Per-user pricing for M365 and Google Workspace licensing plus a managed services fee for the underlying environment. Migration projects are scoped fixed-fee. Ongoing management is part of managed IT support or standalone monthly retainers.
Last Step · Free & No Obligation

Ready to Move to the Cloud — or Stop Overpaying for It?

Book a free 30-minute cloud assessment. We’ll review what you have, what should move, what should stay, and what your environment should look like — no obligation, no sales pressure for a migration you don’t need.

  • ✓ 30-minute cloud assessment
  • ✓ Plain-English migration vs. stay analysis
  • ✓ Cost optimization review
  • ✓ Response within 1 business hour
Or call 1-773-863-3868

Get a Free Cloud Assessment

A quick conversation about your cloud strategy and where it could be improved.

🔒 Your information is private. We respond within 1 business hour.