Tactical CEO IT Bootcamp — Executive 1-on-1, Two-Day Program · 25% OFF service fee if booked before December 31, 2025
Built for everyday SMB CEOs · No jargon

A Discreet, 1-On-1 Bootcamp To Make You An IT-Confident CEO

Most SMB CEOs aren’t IT experts—and they shouldn’t need to be. In 2 focused days, we walk your actual environment together, cut waste, reduce risk, and give you straight answers—privately.

Privacy: this quick check is client-side only; nothing is stored.
25% OFF service fee if booked before December 31, 2025
ROI quick check

If your annual IT spend is between $200k–$1M, a 10% optimization alone often funds this program several times over.

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Designed for the average SMB CEO

We assume a light or weak understanding of IT—because that’s normal. This bootcamp translates tech into plain business language: cost, risk, and value. Everything is on the table, and all questions are welcome—confidentially.

  • Private 1-on-1 with the CEO (optionally include your CFO by request)
  • Walk your real environment: vendors, contracts, apps, access, backups
  • Identify quick wins + 90-day priorities you can act on immediately
  • Build the 4 critical policies and your provider playbook
Why on-site only? Every IT environment is unique. To make you truly confident, we need to walk your setup together, in person. That’s hard to replicate virtually.
Who it’s for
  • CEOs / Presidents (40–500 staff)
  • COOs / CFOs who own IT spend (CFO may join select segments)
  • Boards seeking assurance and clarity
Who it’s not for
  • Group workshops with your wider exec/IT team present
  • Hands-on sysadmin certification training
  • Pure theory with no artifacts or action

The 2-Day working agenda

Day 1
Foundations & Cost Control
9:00–10:30IT translated for CEOs: stack map, critical assets, vendor landscape
10:45–12:00Business impact & downtime math (with your numbers)
1:00–2:30Budget teardown: waste, duplicate tools, skewed SLAs
2:45–4:00Invoice & fraud red flags · “Games vendors play” worksheet
4:00–5:00Day 1 recap · homework (gathering artifacts)
Day 2
Risk, Policy, & Leadership
9:00–10:30Policy pack: AUP, onboarding/offboarding, backups, least-privilege
10:45–12:00Software licensing & audit defense (no pirated surprises)
1:00–2:30Due diligence & liability reduction with a 90-day plan
2:45–4:00Communications: board-level reporting that is actually useful
4:00–5:00Executive briefing & sign-off on your 90-day plan

What you leave with

Executive Brief

Board-ready 1-pager: risks, costs, priorities, investment notes.

Cost-cut list

Stop/keep/renegotiate with quantified savings.

Policy pack

AUP, account lifecycle, backup/DR checklist, provider playbook.

90-day plan

Sequenced actions with owner, effort, cost, and success metrics.

Pricing

25% OFF service fee if booked before December 31, 2025 · Services only. Billing in USD.

On-Site (Flagship)
Discreet 1-on-1

2 days at your location · US & Canada

USD
  • Private CEO 1-on-1 (CFO may join select segments by request)
  • Live review of your contracts, bills, quotes, access, and backups
  • Executive deliverables by end of Day 2
Travel & accommodations billed at cost (cap $1,500).
Executive Trusted IT Advisor
Monthly add-on

Keep momentum with light oversight and decision support.

/month · USD
  • Quarterly working session (90 minutes)
  • Ad-hoc executive Q&A via email
  • Light vendor quote review & red-flag check
  • Progress tracking on your 90-day plan
Add-on is billed monthly; promotional discount applies to bootcamp only.
Payment & Terms
  • 50% to book dates, balance on Day 1
  • Billing in USD; applicable taxes extra
  • Travel & accommodations billed at cost (cap $1,500)
  • Promo applies to bootcamp service fee until December 31, 2025
Private & discreet

Ask anything—without your team in the room. Straight answers only.

Battle-tested checklists

Policies and playbooks refined across real SMB environments.

Cost clarity

You’ll know what to stop, keep, and renegotiate—backed by numbers.

FAQ

CEOs often hold back when other executives or IT staff are present. This program is intentionally private so you can ask anything and surface real concerns. If desired, your CFO may join select segments.

We strongly prefer on-site. Each environment is unique; walking your setup in person is how we build true confidence. Limited exceptions may be considered case-by-case.

We’ll send a short artifact checklist (latest invoices, quotes, org chart, app list). Most CEOs gather this in under 90 minutes.

Yes. We’re provider-agnostic. The output helps you govern providers with clarity and fair expectations.

You can execute the 90-day plan with your team/MSP, or keep momentum with our Executive Trusted IT Advisor monthly add-on.

Ready to command your IT?

Book a 20-minute intro call. We’ll confirm fit, discuss dates, and outline prep.

  • Discreet 1-on-1 delivery (CFO optional)
  • Executive deliverables by Day 2
  • Limited promo until December 31, 2025
IT Support 101 Inc. · +1 (555) 555-1212 · info@itsupport101.com
We’ll never share your info.