Cloud Services in Chicago Built Around What Your Business Actually Needs in the Cloud
Cloud is a tool, not a destination. The question worth asking before any cloud project is not “should we move to the cloud” but “which workloads belong there, which ones don’t, and what does running them well actually cost?”
Datastrive provides cloud services to Chicago businesses that want a straight answer to those questions before anyone starts migrating anything. We plan, migrate, manage and secure cloud environments. We also tell you when staying on-premises makes more sense.
- Chicago-based team supporting businesses across Cook, DuPage, Lake and Will counties
- Microsoft 365 and Google Workspace management as primary cloud platforms
- Cloud migration projects scoped separately from ongoing management so you see what each costs
- Cloud security handled through our cybersecurity services and woven into every cloud engagement
- Part of a broader IT services agreement or available as standalone cloud work
Book a Free Cloud Review
Tell us a little about your business and someone from our team will reach out to set up a time. Your information stays private.
Three Separate Things That Often Get Called “Cloud Services”
One reason cloud projects go sideways is that migration, management and consulting are treated as the same thing and priced together without clear boundaries. We separate them deliberately.
Each of these has its own scope and its own cost. They’re not the same engagement and shouldn’t be bundled unless the bundling makes sense for your situation.
The Cloud Services We Provide in Chicago
Microsoft 365 Management
Microsoft 365 is the most common cloud platform for Chicago small and mid-sized businesses, and also the one that most often runs below its potential. Licenses get bought, email gets set up, and the rest of the platform, including Teams governance, SharePoint structure, OneDrive configuration and security defaults, gets left in whatever state the initial deployment left it.
Our Microsoft 365 management services cover ongoing administration, license management, security configuration, and support for the full M365 environment. For businesses that are not yet on Microsoft 365 or need to move between tenants, Microsoft 365 migration is scoped as a separate project with a clear plan before work begins.
Google Workspace Management
For businesses that built their workflows around Google’s tools, we manage Google Workspace with the same rigor we apply to Microsoft 365: admin configuration, access controls, user provisioning and support. We don’t recommend one platform over the other without understanding how your team actually works.
Cloud Migration
Moving workloads to the cloud is a project that requires understanding dependencies before touching anything. Our cloud migration services start with a workload analysis: what you have, what depends on what, and which pieces belong in the cloud versus which should stay on-premises. Migration is planned before it’s executed and validated before it’s closed.
We’re not going to tell you that every workload should move. Some of them shouldn’t, and moving them anyway tends to add cost and complexity without a business benefit. That’s the conversation we have first.
Cloud Consulting
If you’re making a decision about cloud infrastructure and want independent advice, cloud consulting is available separately from a managed services agreement. Common engagements include reviewing what you already have in the cloud, planning a migration sequence, comparing platform costs, or figuring out the right split between cloud and on-premises for your specific environment.
Which Cloud Service Fits Your Situation?
The right starting point depends on where your environment is today, not on which service is easiest to package.
Most Chicago businesses land somewhere between two of these rows. A short conversation is usually enough to tell which one you are closest to, and what the honest cost of each option looks like.
Hybrid Cloud and Mixed Environments
Most Chicago businesses are already running a hybrid environment, whether they named it that or not. Production servers on-premises, Microsoft 365 in the cloud, maybe a file storage platform in between. The question is usually not whether to go hybrid but how to manage the hybrid setup you already have.
We support businesses where cloud and on-premises workloads coexist. That means consistent identity controls across both environments, a backup strategy that covers both, and a network configuration that connects them without creating security gaps. If you’re considering consolidating to one side or the other, that’s a decision worth talking through before committing.
Cloud Security Is Part of Every Engagement
Cloud environments have their own security surface. Microsoft 365 and Google Workspace tenants are regularly targeted through credential theft, misconfigured sharing settings, legacy authentication bypasses and mailbox compromise. Securing a cloud environment is not the same as securing an on-premises network, and the tools are different.
Cloud security runs through our cybersecurity services: identity and access management, Microsoft 365-specific monitoring and detection through Microsoft 365 security and MDR, email security for cloud-hosted inboxes, and conditional access policies for cloud applications. Every cloud engagement we run includes a baseline security configuration review. What gets added beyond that depends on your risk profile and what your environment requires.
- Identity and access management
- Microsoft 365 monitoring and detection
- Email security for cloud-hosted inboxes
- Conditional access policies for cloud applications
How We Think About Cloud Costs
Cloud costs are often sold on the idea that they replace capital expenditure with predictable monthly spend. That’s sometimes true and sometimes not. A cloud migration that moves workloads that were cheaper on-premises doesn’t save money just because it’s in the cloud. Licensing that grows with headcount without anyone reviewing it adds up. Storage costs in the cloud are real and ongoing.
Before we recommend any cloud change, we look at the cost picture honestly. What will this cost after migration, per month, per user? What are you currently spending on the on-premises alternative? What’s the realistic break-even? We treat your money like it’s ours, which means those numbers get asked and answered before any project starts, not after.
Microsoft 365 Versus Google Workspace
For Chicago businesses deciding between the two platforms, the honest answer is that the right choice depends on your existing workflows, not on a feature comparison chart.
Microsoft 365 tends to fit businesses with established Outlook and Office habits, teams that use Excel heavily, or organizations that need deep SharePoint and Teams configuration for document management and internal communication. It has more complexity in administration, which is also why management matters more.
Google Workspace tends to fit businesses that are already working in Google’s ecosystem, prefer simpler administration, or have teams that collaborate heavily on documents in real time. It’s a capable platform that’s often underestimated.
We’d recommend based on what your team actually does, not on what’s most popular. If you’re already on one platform and it’s working, switching for its own sake rarely makes financial sense.
Cloud Services for Chicago Industries
Different industries have different cloud requirements, driven mostly by the software they use and the data they handle.
Law firms running practice management software need reliable access, careful identity controls and a clear picture of where client data lives. Healthcare practices use clinical applications that have specific hosting and access requirements worth understanding before any migration. Financial services firms work with client financial data across cloud and on-premises systems and need consistent access controls across both. Manufacturers often run production and office technology on separate networks with different cloud readiness. Nonprofits tend to benefit from cloud licensing programs specific to their sector, and we help navigate those.
See the full breakdown on our industries page, including legal, healthcare, financial services, manufacturing and nonprofit.
Cloud Support Across Chicago and the Suburbs
We support businesses in Chicago and throughout the suburbs, including Skokie, Schaumburg, Naperville, Oak Brook, Elk Grove Village, Rosemont, Downers Grove and Aurora. Full coverage details are on our Chicagoland service area page.
Getting Started With Datastrive
A conversation about what you run today.
We go through the workloads you have, where they run now, and what the business needs from them. Nothing gets scoped before that conversation happens.
A review of your current environment.
We look at your Microsoft 365 or Google Workspace tenant, what is still on-premises, and the security configuration behind both.
A written plan with the cost picture.
You get a recommendation that separates migration, ongoing management and consulting, with what each one costs and what we would leave alone.
Frequently Asked Questions About Cloud Services in Chicago
What cloud services does Datastrive provide?
How do you decide what should move to the cloud?
Do you handle Microsoft 365 migration?
What does ongoing cloud management include?
Can you work with us if we’ve already migrated to the cloud?
How is cloud work priced?
How do I get support for a cloud issue as an existing partner?
Talk to Someone About Your Cloud Setup
Whether you’re planning a migration, managing a platform that was set up by someone else, or trying to figure out what your cloud environment is actually costing you, a conversation is the right starting point. We’ll tell you what we’d actually recommend, including what we wouldn’t change.
Book a Free Cloud Review
Tell us a little about your business and someone from our team will reach out to set up a time. Your information stays private.