What To Look For In A Virtual CIO

Every small business knows the trials and tribulations of IT.

Between outdated systems, cloud migrations, and ballooning cyber threats, this is one of the most challenging times in the history of IT. SMBs have it especially hard because limited resources make it impossible to hire a C-level IT executive as an employee.

Enter the virtual CIO (also known as a fractional CIO).

In a nutshell, a vCIO is a seasoned IT leader who offers C-level guidance and services on a fractional-time basis, often as a part of cyber security managed services. They are a contractor, not an employee, making it easier to fill that gap (both in terms of cost and your internal processes). A vCIO may come with a services team behind them, or they may act strictly as a C-level consultant, guiding your internal team on what to implement.

So what should you look for in a vCIO? How do you find one that’s right for you?

We’ll unpack all that and more. But first, let’s look at the benefits of hiring a vCIO.

Benefits of the vCIO model

Outside perspective

A virtual CIO brings an external perspective that’s not particularly invested in your organization’s traditions and culture. While this may sound uncomfortable, it’s actually a key advantage as your organization seeks to transform in the digital age. You may not know what’s holding you back, but a vCIO will have a clear view of what’s working and what isn’t.

Enterprise-class experience available to SMBs

vCIOs come from diverse backgrounds, but most have broad experience running IT departments at larger organizations. A seasoned vCIO brings enterprise-class knowledge to every client’s environment and strategy. It’s a level of expertise that most SMBs can’t attain with an in-house hire.


Simply put, a vCIO is far more affordable than an in-house executive. The person who serves as your vCIO will put in fractional time, which reduces their cost significantly. If the vCIO comes with an execution team, you benefit from the economies of scale offered by the agency model. In essence, you get access to “hands and feet” specialists in various IT domains without the expense of keeping each specialist on staff.

What to look for in a virtual CIO

Broad experience

A vCIO should have some knowledge of your industry. But more importantly, they should have experience beyond your industry. The more broadly a vCIO has worked, the greater their ability to crystalize best practices that apply across the board. This is a huge advantage, particularly if your industry faces unique challenges that insiders consider quite difficult to solve. A vCIO with broad experience will bring solutions and perspective that you can’t get strictly from within your industry.

Flexible services

No two organizations are alike. This is why a good vCIO will offer service packages that fit a wide range of situations and internal team configurations. This is especially important because things can change fast in IT. If you have two part-time IT employees, your virtual CIO may need to step up their fractional services if one employee leaves. Likewise, if you decide to hire more IT specialists in-house, your virtual CIO should be able to adapt.

If a vCIO service needs every client to fit the same mold, this could be a red flag. Make sure you know what your organization needs today, what could happen tomorrow, and how a vCIO will need to adjust in that shifting scenario.

Right size, right number of clients per vCIO

Make sure your vCIO offers the right level of personalized service. On one end of the spectrum, a virtual CIO with many clients will bring an incredibly broad perspective—yet the attention and solutions they provide may be less personalized.

On the other end of the spectrum, fewer clients per vCIO will give you more time, attention, and personalization—likely at the cost of a broad perspective.

There’s no right answer here, and every organization will land somewhere different on that spectrum. The key is to ask the right questions as you evaluate vCIO services.

Questions to ask as you evaluate vCIOs

As with any vendor search, the answers that vendors provide are useful for making a final decision. But the answers are also useful in building your own understanding of your scenario. While you’ll ultimately choose one vCIO, ideally, you’ll gain a wealth of intelligence from vendors who didn’t make the cut. You should absolutely use these answers to define the path forward with your selected vCIO.

Here are some key questions to ask.

  • What are the biggest IT challenges for an organization of our size? This question will help you determine how familiar the vCIO is with your scenario.
  • What are some common IT challenges in our industry? This will help you determine how well the vCIO provider knows your industry. If industry-specific knowledge is important for your scenario, this question will have a critical role in whittling down your consideration set.
  • As our vCIO, what high-priority items would you address in the first 90 days? While this question only makes sense after a few calls with the vCIO, you’ll want to ask it eventually—and before you make a decision. The right vCIO will have a clear set of prioritized objectives to address first. They should be able to back up those claims with data and communication in plain language.
  • How do you interface with cybersecurity? A CIO is not the same thing as a CISO (chief information security officer). Make sure you understand what your virtual CIO is offering, and what they’re not offering. HINT: A vCIO who can also connect you with cyber resources is a huge asset. That’s one reason we offer integrated cybersecurity and managed services here at Corsica.
  • What do you think of Microsoft Copilot vs. ChatGPT? If your organization isn’t using ChatGPT, this may not be a factor. However, if you are, you’ll want to understand the implications of using one AI over the other. A good vCIO should be able to advise. Read more here: Microsoft Copilot vs. ChatGPT.
  • Do you offer the CIO component only, or do you come with a services team? Some vCIOs act strictly as executive consultants. They give you a strategic roadmap, and your staff (or outsourced resources from another provider) will implement the vision. This model works well for larger organizations, but SMBs tend to do better when their vCIO comes with a services team. In this scenario, the vCIO provides the vision, then directs their team in implementing it—either on their own, or in collaboration with your internal team.
  • If you come with a services team, what types of domain expertise does your team have? Here’s where economies of scale come into play. A boutique vCIO shop may have fewer domain-specific resources available. This may force them to specialize or limit their service offerings. In contrast, a larger provider should have every conceivable type of expert on staff. The right vCIO package will give you access to these genius-level resources as needed.
  • Will we work with a dedicated vCIO, or will our requests go to a pool of vCIOs? At first glance, a dedicated vCIO might sound like the best option. However, either model can be a good fit in different scenarios. A dedicated resource will get to know the specifics of your organization over time, but single-threadedness becomes a larger risk. In contrast, a pool of vCIOs may have less capacity to learn the quirks of your company—but they will provide greater continuity over the long haul. Again, there’s no right answer that works for every company.
  • What SLA(s) do you offer for tickets and projects? If a critical system goes down, how fast will your vCIO and/or their team respond? What kind of support access do you get? You’ll also want to ask about project scoping and typical timelines for various initiatives.

The takeaway: Know your strengths and weaknesses (and ask tough questions)

While finding a vCIO can be nerve-wracking, the outcome is definitely worth it. There’s no replacement for having that expert perspective guiding your strategic IT roadmap. Take careful stock of the resources you have and use the evaluation process to learn about any weaknesses you didn’t know you had. What you learn from this process will help you select the right vCIO for your organization.

Want to learn more about virtual CIO services?

Reach out to schedule a security consultation with our IT specialists.
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George Anderson
George Anderson is a blogger and trade journalist in IT and technology. Covering topics from IT to ecommerce to digital transformation, his work has appeared in numerous outlets around the internet. He loves writing on complex subjects in plain language to help companies succeed with technology.

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