The two-day boot camp for vCIO success.
Most MSPs promise strategic guidance and deliver a ticket report. Two days, in person, that turn your account team into the technology leader your clients plan around, and give them the practical materials to prove it at the next meeting.
Nobody is born a vCIO.
It is a discipline you can learn.
Your team already knows the technology. That was never the gap. The gap is running a meeting where a business owner leans forward, funds the roadmap, and asks what comes next. That is a learnable skill with a repeatable structure behind it, and two days in a room is how it gets learned.
2 days
In person, hands on
10 seats
One small cohort
1 live client
Real work, not case studies
Role play
Live, with coaching
Send the people who sit in front of clients.
Experience level does not matter. Owning the client relationship does.
The new vCIO
Promoted last quarter and learning on the client’s dime. You leave with a structure for every meeting, so you stop improvising in front of the people paying you.
The account manager
You already own the relationship. Now own the technology plan behind it, so the conversation moves from tickets and invoices to where the business is going.
The owner who is still the vCIO
Every strategic client still runs through you. Write it down as a documented process here, so you can hand it to someone else and it survives the handoff.
Two days of learning IT leadership excellence.
Lecture, lab work and live practice, in that order, every day. Bring one real client account. Every exercise runs against it, so what you build in the room is work you can actually use.
1 Day One
Standards, numbers and the plan. You will know what world class looks like, and you will be able to build and defend a funded plan.
- The vCIO mandate. What a world class vCIO owns, and what gets handed back to the service desk.
- Grade your practice. Score yourself against the maturity benchmark and find the gap costing you most.
- Outcomes, not tickets. Turn technical work into business outcomes an owner will act on.
Networking lunch with the cohort
- Read the numbers. Get enough from a client’s financial statements to be useful in the room.
- Roadmap and budget. Build a fundable three year plan, with asset lifecycle and refresh timing priced in.
- Role play: pitch the plan. Present your roadmap and budget to the room and take the pushback.
Group dinner with the cohort and instructors
2 Day Two
Risk, automation and the room. You will run the meeting, absorb the pushback, and walk out with an approved plan.
- Risk in business terms. Security, compliance and continuity as a conversation the CEO owns.
- Automate the QBR. Walk the whole loop, from live client data to a finished deck.
- AI in the workflow. Score a client’s AI readiness and build the transformation roadmap.
Networking lunch with the cohort
- Discovery that lands. The questions that surface real business risk instead of a wish list.
- Adoption and standards. Drive the stack across the base and advance the roadmap every quarter.
- Role play: run the room. Deliver a full QBR live and handle every objection thrown at you.
Group dinner and graduation
Automate your QBRs.
Day two walks the whole loop end to end. Schedule, prep, wrap, opportunities, quotes, plan update, report. Prep that used to eat days gets handed to the software, and you leave able to run it on your own client base.
Master AI with Strategy Overview.
Your clients are already asking about AI. You will leave able to score their readiness, build the transformation roadmap, budget it, and move a client from reactive to AI enabled without hand waving.
Training that survives the flight home.
Most workshops end with a binder nobody opens. Six things make this one stick.
Drawn from hundreds of MSPs
We sit inside hundreds of vCIO practices. You get the pattern that keeps working across all of them, not one operator's war stories.
You practice on a real client
Bring one live account. Every exercise runs against it. You go home with a roadmap, a budget and a deck for an account you actually bill.
Practical materials you keep
Every worksheet, template and script you build in the room leaves with you, ready to rebrand and reuse across the whole client base.
Live role play, not lectures
You present, you get interrupted, you get critiqued. Both days end with you running the meeting in front of the room.
Your workspace, tuned to you
Templates, standards and assessment criteria configured around how your practice actually runs, loaded into Strategy Overview before you fly home.
Invites to the alumni calls
Graduation is the start. Every graduate gets a standing invite to the post boot camp alumni calls, where the cohort keeps working the problem together.
One price. Everything in it.
No upsell at the back of the room. Tuition covers the instruction, the practical materials, the food, the graduation and a standing invite to the alumni calls.
→ Two full days of instruction. In person, capped at ten seats, taught by practitioners.
→ Your own client, worked live. Every exercise runs against a real account you bring with you.
→ The full toolkit. Templates, worksheets, scripts and assessment criteria, yours to rebrand and reuse.
→ A workspace configured to you. Strategy Overview set up around your standards before you leave the room.
→ Role play with real feedback. You present, the room pushes back, the instructors critique.
→ Every meal covered. Welcome reception, breakfast and lunch both days, and the group dinner.
→ Graduation and certification. Proof your team can run the process, not just proof they attended.
→ Standing alumni invites. Keep working the problem with your cohort long after you get home.
FAQ
Do I have to be a Strategy Overview customer?
No. The playbook works on any stack and plenty of attendees are not customers. Customers get one extra thing: they leave with their workspace already configured.
Who should I send?
Anyone who sits in front of clients and owns the technology plan. The MSPs who get the most out of it send the vCIO and the account manager together.
How big is the cohort?
Capped at 10. Small enough that you present your own work and get critiqued on it, rather than watching someone else present theirs.
What should I bring?
A laptop and one real client account you are willing to work on for both days. The more real the account, the more you take home.
What does it cost?
Tuition depends on the session and how many seats you take, and there are team rates. Request info and we will send current pricing the same day.
Can you run it for my team only?
Yes. Private boot camps run on site at your office, built around your stack and your client base. Say so in the form and we will send options.
Taught by IT strategy veterans.
Practitioners, not career trainers. Between us we have run thousands of QBRs and led IT strategy for hundreds of clients, and we build the software that makes the process repeatable.
Alex Markov
CEO and Co-Founder
Jesse Smith
Chief Strategy Officer
Dan Gamez
Strategy Advisor
Paul Grenci
Strategy Advisor
Nashville first. New York next.
Two cohorts, ten seats each. Exact dates and venues go to the list before they go public, along with tuition and the full curriculum.
Nashville, Tennessee
First quarter 2027
Ten seats. Exact dates and the venue go out to the list first, with tuition and the full agenda.
New York City
Third quarter 2027
Ten seats. Exact dates and the venue go out to the list first, with tuition and the full agenda.
Request More Information
Two minutes. You get the full curriculum, the session schedule and tuition inside one business day. No sales sequence, no drip.
Your clients will follow the person with the plan.
Two days in a room is the fastest way to become that person. Ten seats per cohort.