vCIO Peer Groups to Build IT Leadership Excellence
Strategy Overview vCIO Peer Groups put your vCIOs and TAMs in a confidential room with peers doing the same job at non-competing MSPs. Twelve facilitated sessions a year, plus two in person. Every member leaves every session with a move to make.
Your vCIO is the quarterback of the MSP.
Nobody is coaching them.
The vCIO calls the plays for every client: the roadmap, the budget, the standards, the hard conversations. It is the highest leverage seat in your MSP.
Owners have peer groups. Service managers have peer groups. CFOs, sales leaders and security leads are all covered. The quarterback is reading the field alone.
- No benchmark for what good strategy looks like
- Nobody to pressure test a roadmap or a budget before the client sees it
- Every hard client conversation feels like the first time anyone has had it
- Skills built by trial and error in front of your best accounts
- Turnover in the seat resets the whole practice
10
members per group, maximum, all in non-competing markets
12
facilitated 90 minute sessions a year
2
full day in-person meetings a year
How a peer group
actually works
A vCIO peer group is a small closed room of vCIOs, TAMs and account managers from non-competing MSPs who meet on a fixed cadence to compare process, benchmark their cadence, and hold each other to what they said they would do.
You bring a real client situation. The group takes it apart. You leave with a move.
How it works
Monthly virtual sessions
Ninety minutes, once a month, facilitated. One member brings a live client case, the group works it, everyone leaves with an action and reports back next month.
Two in-person meetings a year
Full day working sessions. Deep dives on packaging, pricing conversations and defending a roadmap, plus the relationships that outlast any single meeting.
Confidential and non-competing
Up to ten members, screened by market so no two members compete for the same client. What is said in the group stays in the group.
What you work on
The agenda is set by the room, drawn from the situations members are actually in.
Running the Technology Strategy Meeting
Cadence, agenda, and what earns a decision instead of a nod.
Roadmaps clients approve
Multi year plans tied to business outcomes, not refresh cycles.
Budget and spend conversations
Presenting IT spend so it reads as investment, not as a bill.
Standards and stack discipline
Moving a client onto your standard without a fight, and what to do when they refuse.
The reactive to strategic shift
Selling strategy into an account that only calls when something breaks.
Benchmarking your own practice
How many accounts per vCIO, how often, how deep. Measured against the room.
Who belongs
in the room
- vCIOs and virtual CIOs
- Technical Account Managers
- Account managers and client success managers who carry a strategy number
- Owners still sitting in the vCIO seat themselves
Groups are placed by role and by the size and maturity of the practice, so the room is genuinely peers. A vCIO carrying 40 accounts and a vCIO carrying 8 need different conversations, and they get them.
Grounded in the frameworks
the industry already trusts
Facilitation draws on the operational maturity work MSPs already know: the world-class MSP model and the vCIO and TAM role definitions from TruMethods (Gary Pica), and Operational Maturity Level (OML) benchmarking from Service Leadership, now part of ConnectWise.
We did not invent those frameworks. We run the room where your team learns to execute them.
How to join
1
Apply
A short application: your role, your market, and the size of the practice you run.
2
Placement call
Thirty minutes to understand your goals, confirm there is no market conflict, and cover cost.
3
Get matched
You are placed in the group that fits your role and stage, and onboarded before your first session.
FAQ
Who facilitates the groups?
Every group is facilitated by a Strategy Overview practice lead who has run vCIO programs and reviewed hundreds of MSP strategy processes. The facilitator keeps the session on agenda, brings benchmarks into the room, and holds members to the commitments they made last month.
Do I have to be a Strategy Overview customer?
No. The groups are open to vCIOs and TAMs at any MSP. You do not need to run Strategy Overview to take part.
How do you keep competitors out of my group?
Placement is screened by geography and target market. If your application overlaps an existing member’s market, you go in a different group. That is why placement happens on a call and not through a checkout page.
What is the time commitment?
One 90 minute virtual session a month, plus two full day in-person meetings a year. When it is your turn to bring a case you will spend an extra hour or two preparing that month.
What does it cost?
Cost is covered on the placement call, once we know which group fits your role and stage. Apply and we will walk you through it.
Is this the same as vCIO Mastery training?
No. vCIO Mastery is structured training that teaches the process end to end. The peer group is ongoing: you bring live client situations and the room works on them month after month. Plenty of members do both, and the training makes the group time more useful.
Can I send more than one person from my MSP?
Yes, but they are placed in different groups. One member per company per group keeps the discussion honest.
What if the group is not the right fit?
Tell us after your first two sessions. We will move you to a better fitting group or step you out. No contract fight.
Apply to join a
vCIO peer group
Tell us about your role and your market. We come back within two business days with the groups that fit.
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