Chicago IT Support and Outsourcing Selection Guide

Chicago IT Support and Outsourcing Selection Guide
Published May 21, 2020

Your business has decided it’s time to change your Information IT support / Information Technology department. Whether you have outgrown your current solution, had one too many failures, or just know there must be a better way this guide will simplify the process.

We have guided thousands of small businesses through the process of selecting their Chicago IT support / department and it can be considerably easier than you might imagine whether you are looking to outsource IT, insource IT or a combination of both. To simplify the process we will describe the 7 components of an IT department and the 4 IT support models.

Before we get started, let’s make sure you are reading the right guide:

  • You are based in Greater Chicago land and have between 15 and 250 full time equivalent computer using staff members.
  • You need your business and IT to be running smoothly with a new chicago based IT support solution (this guide does not cover remote only solutions, as we have not seen that succeed yet, though it certainly might in the future – in the mean time, there area a many great IT based Chicago companies).
  • You need a service desk / help desk support with reasonable response time.
  • Protecting your data is important.
  • You either have no internal IT, you are considering mixing internal and external IT, you want to switch from one to the other, or have a current IT firm that does hourly support or managed IT services.

7 IT Department Components

Now that we know you are at the right place, lets define exactly what all IT support can entail. When most people we meet say they are looking better / different IT support, all they think of is help desk support and projects. So we will start there and expand:

  1. Service / Help desk / Support team
    • One or more onsite or remote individuals that helps fix problems or makes minor chases that your staff requests. 
  2. Project Department
    • A department of project engineers that implements more significant changes like network and server upgrades and installations of new solutions.
  3. Central Services
    • Even if not named, all IT support models have a list of solutions they try to standardize on to give you more predictable results. Patch management, monitoring, antivirus, antispam, disaster recovery, backup, cloud services, security training / testing, etc.
  4. Virtual CIO / Fractional CIO
    • Again, even if not named, everyone will give you advice on what you should do with technology though there is a dramatic variency in the results. The results start with that of a Virtual CO (Captain Obvious) that tell you to replace your equipment every 5 years and reach their peak with CIO’s that lead you in digital transformations that accelerate your business goal attainment and efficiency.
  5. Alignment / System Analysts
    • Think of this department as the technology auditors . Analysts look for misalignments with the sole  purpose of reducing issues caused by IT and optimizing the solutions that are in place. Most people that we meet with are looking for “proactive” support, which we have only seen provided by the inclusion of this component of the IT department with dedicated individuals that do not work on fixing problems, but exclusively on preventing them. System Analysts create the misalignment reports, so that the Virtual CIO / Fraction CIO can successfully steer the business to achieve higher results.
  6. Security
  7. Application / Software Development
    • Responsible for the creation and integration of proprietary systems for small or medium businesses.


4 IT Support Models

Now that you have a high level understanding of all the components of an IT department, lets go over the 4 models that are available to small and medium businesses that have between 15 and 250 full time equivalent computer using staff members:

  1. Internal Staff
    • Dedicated full time W2 employee(s) to IT. Typically only done by businesses with more than 50 full time equivalent computer using staff members in a single office. 
    • To model may be combined with and of the other 3 models and referred to as co-managed and deserves its own guide. Until that guide is authored, feel free to contact us for a discussion.
  2. Hourly IT Firms / IT Consultant(s)
    • You and your staff organize work to be done by them. In some instances, they can setup monitoring to be alerted to some issues that they can autonomously work on with your permission. 
    • This model was the most popular model until 2015, and still is for small businesses with less than 10 staff. IT Firms that are willing to work on an hourly basis (sometimes purchased in blocks of hours) have greatly reduced in favor of the Managed Service Provider (MSP) model. You will have more success looking for independent IT Consultants. 
  3. Managed Service Provider 
    • The most popular model in Chicago since 2015 with hundreds of providers. You pay a flat monthly fee based on the size of your environment with unlimited remote support. Hourly IT Firms benefit from being able to predict their revenue, you get a bill that you can budget for. 
  4. Aligned IT
    • Common in larger businesses, Aligned IT is becoming necessary for small and medium businesses as they begin their digital transformations to being a technology enabled organization. 
    • Aligned IT evolves from the MSP models flat fee concept with:
      1. Strategic planning process that maps each of your department’s business objects against a technology plan.
      2. Technology alignment to reduce issues caused by technology, what most we interview think of as “proactive”, and optimize existing systems.

Evaluation Next-Steps

You now need to organize your thoughts and decide on the key results you want from your future IT Support model. 

  • Proactive vs Reactive
  • Strategic vs Tactical

For secondary objectives you have a list of other requirements:

  • Hours of coverage
  • Transparency – access to documentation of your environment
  • Location
  • Experience supporting similar businesses
  • etc.

To help you organize your decision, we have created an evaluation form that you can download here.

If we can be of any further assistance, please don’t hesitate to reach out. Our mission is helping small business and their staff, and we would be happy to help guide you at no cost! Contact us.

You may also like

Mar 10, 2020

Your Silos are Crushing You

Symptoms: Communication comes up as one of the main reasons why a small business is not working well...

Feb 11, 2020

Start Connecting Engagement with Performance

Symptom: Lower morale, reduced productivity, an uptick in employee complaints “We want to work in a...

Sep 09, 2019

Why Exists

Dear Small businesses and staff, I have struggled since early 2009, before founding, to ar...