True vCIO value isn’t delivered in tickets or reports. It’s delivered in the moments you get face time with owners, CEOs, and executive teams.
Those meetings are rare. Most MSPs are pushed down to operational contacts. So when a vCIO gets time with a real decision-maker, the goal is simple: reinforce trust, show leadership, and create excitement about the future.
The meeting must be a “WOW”!
Here’s the framework we use in our MSP:
1. Eliminate Operational Noise Before the Meeting
A vCIO should never walk into a strategic meeting with unresolved issues.
If tickets are open or projects are stuck, executives will focus on that, and strategy disappears.
Strategic IT meetings are not for SLAs, ticket counts, or operational metrics.
If operations aren’t clean, you’re not ready to lead a strategic conversation.
2. Start with the Current State (High-Level)
Executives appreciate a clear reminder of what they have today.
A strong vCIO starts with:
- Assets and environment scale
- The deployed IT and security stack
- Key assessment results and risk posture
This grounds the discussion and sets the stage.
3. Shift Quickly to the Future
The purpose of a vCIO meeting is not to review the past.
It’s to sell the future vision of IT every single year.
Move the conversation to:
- What’s changing
- What’s coming next
- What risks are being proactively addressed
This is where excitement is created.
4. Tie Every Initiative to Business Outcomes
vCIOs don’t talk about tools, they talk about impact.
Every initiative should connect to:
- Risk reduction
- Business continuity
- Scalability and growth
- Operational efficiency
If the business outcome isn’t clear, the value won’t be either.
5. Shift Quickly to the Future
vCIO meetings should feel like leadership conversations, not presentations.
They should stay high-level, visual, and dynamic with the ability to drill down only if the executive asks. That’s exactly why we built PropelLive to support strategic, executive-facing vCIO conversations.
The vCIO Outcome That Matters
When done right, executives leave the meeting feeling:
- Confident in their decision to work with you
- Assured there’s a clear roadmap
- Excited about what’s ahead
You may only get one or two chances a year with true decision-makers.
For a vCIO, those moments define your value, make them count!
It must be a “WOW”!
Simon is the President of S3 Technologies, a leading Canadian MSP he co-founded in 2003. He built and scaled the vCIO team which eventually lead to him co-founding Propel Your MSP in 2018 to help MSPs with their vCIO services.
