How Not to Onboard a vCIO

Here’s one of the biggest mistakes I’ve made in our MSP, and that I see other MSPs make all the time: assigning a new vCIO to a new client.

On paper, it makes sense. Your experienced vCIOs are slammed, you just brought in someone new, and hey, this new client needs a vCIO ASAP. The new vCIO doesn’t have any accounts yet. Problem solved, right?

No. This is a recipe for disaster.

The Real Problem

When a new vCIO is still getting up to speed, they’re not ready to lead a strategic relationship. Even if they’ve got vCIO experience elsewhere, they haven’t yet proven they can deliver your version of a vCIO.

Now pair that with a brand-new client, someone who’s still figuring out if hiring your MSP was the right decision. They’re watching closely. They’re forming impressions. And if their first strategic interaction with your company feels shaky or underwhelming, it’s really tough to recover from that.

But here’s the biggest issue: if the vCIO doesn’t work out, you must reassign that client to someone else. That kind of transition shakes confidence and creates friction right when you should be building trust.

Do It the Right Way

At this point, we have a clear rule at our MSP: we don’t assign a new vCIO to any client (new or existing) until they’ve proven they’re ready.

Instead, we have them:

• Shadow experienced vCIOs to see how we run strategic meetings/QBRs, build roadmaps, and lead client conversations.
• Work in the background on proposals, budgets, and roadmaps.This way they can get familiar with both the client and our internal standards.
• Take ownership gradually, and ideally with clients they’ve already supported in another role (we try to hire internally).

When we are ready to assign a new vCIO to a client, it’s way safer to start with an existing client where we already have a strong relationship. If something’s not clicking, the client will tell us, and we can adjust without doing major damage.

With new clients, you don’t have that luxury. You only get one shot to make a great first impression, and it’s not worth risking that just to balance capacity.

TLDR

I know how tempting it is to assign the new client to the new vCIO. Everyone’s busy, and it feels like the easiest solution. But the easy way often creates more problems later.

If there’s one thing we’ve learned:

Never assign a new vCIO to a new client. And avoid assigning any client to a new vCIO until they’re fully ready.

Build the bench. Train in the background. Then let them take the lead when the timing is right.