Core Services
IT Consulting & vCIO — Chicago, IL
Technology That Works For Your Business
Fairway IT’s consulting and virtual CIO services give you a proactive technology strategy aligned to your business goals, budget, and growth plans.
✓ vCIO & strategic roadmapping
✓ IT budgeting & planning
✓ Vendor-neutral recommendations
Consulting Services
Strategic IT Support for Growing Businesses
From your annual technology budget to a single vendor decision, Fairway IT provides the expertise to make smart, confident IT choices.
01
SERVICE
IT Roadmapping
A documented, prioritized 3-year technology plan aligned to your business goals — covering infrastructure refresh cycles, security improvements, software upgrades, compliance timelines, and budget by fiscal year. No more reactive, surprise IT spending.
02
SERVICE
IT Budget Planning
We build a detailed annual IT budget — hardware, software, licensing, services, and project costs — so you can plan, forecast, and avoid the sudden expense that derails a quarter. Includes multi-year capital planning for hardware refresh cycles.
03
SERVICE
Virtual CIO (vCIO)
A dedicated technology advisor who attends leadership meetings, translates business goals into IT decisions, reviews vendor proposals, and ensures your technology investments are aligned to your growth strategy — without a CIO salary on your books.
04
SERVICE
IT Project Management
Need to deploy a new ERP, move offices, or roll out a new business application? We manage complex IT projects end to end — scoping, vendor coordination, timelines, testing, and go-live support — so your business doesn’t bear the project management burden.
05
SERVICE
Vendor Selection & Procurement
We evaluate technology vendors on your behalf — hardware, software, internet providers, phone systems, and line-of-business applications — with no vendor kickbacks or hidden incentives. You get honest, objective recommendations based on your needs.
06
SERVICE
IT Assessments & Due Diligence
Buying or merging with another business? We audit the target company’s IT environment — infrastructure, security posture, licensing, contracts, and liabilities — so you know exactly what you’re inheriting before the deal closes.
vCIO vs. In-House IT Director
Fairway vCIO
✓ Strategic IT leadership
✓ Multi-year roadmapping
✓ Budget planning & forecasting
✓ Vendor-neutral advice
✓ Included in your plan
In-House IT Director
✓ Strategic IT leadership
✗ Often tactical-only
✗ May lack finance skills
✗ Vendor relationships vary
✗ $120K–$180K/year salary
Strategic IT leadership at a fraction of the cost of a hire
Is This You?
Signs Your Business Needs IT Consulting
If any of these sound familiar, a strategic IT partnership could change the way your business uses technology — and how much you spend on it.
💸 “We keep getting surprise IT invoices with no budget for them.”
Reactive IT spending is unpredictable and expensive. An IT roadmap and annual budget prevents surprises by planning hardware refresh cycles and project costs 2–3 years in advance.
🤷 “We’re not sure if our technology is actually keeping up with our growth.”
If your systems feel like they’re barely keeping up, they probably are. A technology assessment identifies where your infrastructure is at risk before it becomes a bottleneck.
📦 “We’re paying for software we don’t fully use or understand.”
The average business overspends on technology by 20–30% through redundant subscriptions, oversized licenses, and underutilized tools. A SaaS and license audit often uncovers immediate savings.
🏗️ “We have a big IT project coming up and don’t know how to manage it.”
Office moves, ERP deployments, phone system replacements — complex projects require dedicated project management or they run over time and over budget. We own the project so you don’t have to.
🔗 “Our vendor keeps recommending things, and we have no way to evaluate them.”
When the person selling you something is also advising you on what to buy, there’s a conflict of interest. Fairway IT provides vendor-neutral guidance with no incentive other than your success.
📈 “We’re growing fast, and IT feels like it’s always behind.”
Scaling a business is hard enough without technology slowing you down. We build forward-looking IT strategies that scale ahead of your growth — not in reaction to it.
Deliverable Spotlight
What Your IT Roadmap Looks Like
An IT roadmap isn’t a vague strategy document — it’s a practical, actionable plan with specific initiatives, timelines, and budget figures. We build it collaboratively with your leadership team and update it quarterly as your business evolves.
✓ Current state assessment — infrastructure, software, security, and staffing
✓ Risk register highlighting vulnerabilities and compliance gaps
✓ 3-year initiative roadmap with quarterly milestones
✓ Budget by fiscal year — capital and operational spend
✓ Vendor recommendations with cost comparisons
✓ Alignment to business goals — growth, efficiency, compliance, risk reduction
Sample IT Roadmap — Year 1
Q1
Security Baseline & EDR Deployment
Deploy EDR, MFA, and DNS filtering across all endpoints. Close critical security gaps identified in assessment.
Q2
Microsoft 365 Migration & Optimization
Migrate from on-prem Exchange to M365. Configure SharePoint, Teams, and Intune device management.
Q3
Compliance Gap Remediation
Address HIPAA / PCI DSS gaps — access controls, encryption, audit logging, and policy documentation.
Q4
Hardware Refresh & Disaster Recovery
Replace end-of-life workstations. Implement cloud DR with tested backup and documented recovery runbooks.
Our Process
How IT Consulting Works at Fairway IT
We start by understanding your business — not just your technology. From there, everything we recommend is tied to a real business outcome.
01
Business Discovery
We meet with your leadership team to understand your goals, challenges, growth plans, and technology frustrations — before we ever look at a server or network.
02
IT Assessment
We audit your current environment — infrastructure, software, security, compliance, and spend — mapping what you have against where you need to go.
03
Roadmap & Budget
We deliver a prioritized 3-year IT roadmap with quarterly milestones and a detailed annual budget — a real plan, not a 40-page report you’ll never read again.
04
Ongoing vCIO
Quarterly business reviews, annual roadmap updates, vendor proposal reviews, and standing access to your dedicated technology advisor as your business evolves.
Frequently Asked Questions
IT Consulting Questions, Answered
A virtual CIO (vCIO) is a fractional technology executive who provides the strategic IT leadership of a full-time CIO — without the full-time salary. Fairway IT’s vCIO service gives you a dedicated technology advisor who understands your business goals, builds a multi-year IT roadmap, manages your IT budget, and aligns technology decisions to your growth strategy. Most Chicago businesses get a full-time CIO-level perspective for a fraction of the $120,000–$180,000 annual cost of a hire.
Managed IT services handle the day-to-day operational side of IT — help desk support, monitoring, patching, and maintenance. IT consulting focuses on the strategic side — where should your technology be in 3 years, what should you budget, which vendors should you choose, and how does technology support your business goals. Fairway IT provides both, so your IT is managed operationally and guided strategically from a single partner.
An IT roadmap is a multi-year plan that documents your current technology state, identifies gaps and risks, and lays out a prioritized schedule of investments and improvements aligned to your business goals. It covers infrastructure refresh cycles, software upgrades, security improvements, compliance timelines, and staffing or tool changes — with budget estimates for each initiative by fiscal year.
Yes. We recommend the technology that is right for your business — not the technology with the best margin for us. We do not take vendor referral fees or commissions that would influence our recommendations. When we suggest a product or platform, it’s because it’s the best fit for your needs, budget, and long-term goals.
Yes. We conduct IT due diligence assessments for companies acquiring or merging with other businesses. This includes evaluating the target company’s infrastructure, cybersecurity posture, software licensing, contracts, compliance status, and technical debt — giving you a clear picture of what you’re inheriting before the transaction closes and what integration costs to expect.
Let’s Build a Technology Strategy That Actually Works
Stop making reactive IT decisions. Fairway IT will help you build a clear technology roadmap, realistic budget, and a plan that aligns your IT investments to your business goals.
One conversation. A clear picture of where your technology should be heading.