Executive CEO-focused IT Services - Advisory, Bootcamps & Cost Audits. Canada & USA.
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Onsite Only • 2 Days • No Jargon • Limited to 12 Boot Camps per Quarter

CEO Boot Camp — Master IT in Plain English

A focused, 2-day onsite IT boot camp for CEOs and SMB Owners who don’t live in the weeds of technology. We cut out the jargon and explain everything in plain English—so you’ll understand how your IT works, what it costs, and how to manage it with confidence. We specialize in translating Geek → English and English → Geek, teaching technical terms only after you grasp them in simple business language.

Get Started: Download our free “CEO’s IT Checklist: 10 Questions to Ask Your IT Team”.

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Who it’s for
  • CEOs and Owners who feel left in the dark by technical explanations.
  • Leaders who want IT explained in plain business language, not jargon.
  • Executives unsure where their IT budget goes or what value they’re getting.
  • Companies where IT struggles to communicate clearly with leadership.
  • Any CEO or Owner who wants confidence to ask tough questions and make informed decisions.
Includes our CEO Tactical Guide to IT (handbook) — a quick-reference resource to refresh your memory after the boot camp.
Who it’s not for
  • Teams seeking deep hands-on engineering or tool configuration.
  • Pure technical audits (see comparison below).
What Clients Say
Trusted by 50+ SMBs in manufacturing, retail, professional services, and more—helping them save millions annually on IT costs.

“This boot camp gave me the confidence to renegotiate our IT contracts, saving us $30K annually.”

— CEO, Manufacturing Firm (85 employees)

“Finally, I understand what our IT team is talking about. The plain-English approach was a game-changer.”

— Owner, Retail Business

“The 90-day plan helped us streamline our IT budget and prioritize cybersecurity.”

— CEO, Professional Services

Why this Boot Camp — Outcomes You Can Expect
  • Confidence: Understand the “moving parts” of your technology—computers, servers, software, networks, and people.
  • Control: Know what to ask vendors, how to read quotes, and where your IT budget actually goes.
  • Clarity: See how everything fits together—from email and file storage to cybersecurity and cloud tools—without geek-speak.
  • Action: Walk away with a prioritized 90-day plan and a clear one-year outline.
  • Translation: We bridge Geek ↔ English so you get straight, usable answers.
We avoid jargon. If a term (“cloud”, “licensing”) appears, we explain it in simple business language first.
No Jargon. No Fluff.

You’ll clearly understand:

  • Computers, networks, and security basics—how everything connects and stays protected.
  • The software your company relies on—owned vs. subscription (“cloud” / SaaS).
  • Renewals and subscriptions—what you’re paying for, how often, and what to watch for.
  • Support models—break/fix vs. managed services.
  • Your IT budget—hidden costs and savings opportunities.
Case Study: A retail CEO identified $25K in redundant licenses within 3 months.
The 2-Day Onsite Agenda
Day 1: Understand Your IT

Get a clear picture and quick wins.

Day 2: Take Control

Master costs, strategy, and communication.

Day 1 — Foundations & Walkthrough
  • 📋 Executive briefing: what’s working, what’s not, and your goals.
  • 🖥️ Overview of “moving parts”: computers, servers, internet, phones, security.
  • 🚶 Environment walkthrough: how tech is set up today.
  • 🛠️ Support flow: who handles problems and how they resolve.
  • ✅ Quick wins identified: immediate improvements.
Day 2 — Software, Costs & Leadership Enablement

Morning: Software & Costs

  • 📊 Review core software (office, email, accounting, industry apps).
  • ☁️ Understand subscriptions (SaaS) vs. perpetual licenses.
  • 💸 Licenses & renewals: who pays, how often, and why.
  • 📉 IT budget deep-dive: contracts, hidden fees, reduction opportunities.

Afternoon: Strategy & Leadership

  • 📅 Your plan: prioritized 90-day list + one-year outline.
  • 🤔 Decision frameworks: buy vs. build, keep vs. move to cloud.
  • 👥 Team model & communication: accountability, simple metrics, board talk tracks.
  • ❓ Final Q&A and CEO debrief.
Note: We keep terms simple and pace comfortable with breaks and Q&A. Onsite days are consecutive. Travel & accommodations billed at cost.
What’s Included
  • Pre-work intake (10–15 min) to tailor your boot camp
  • Two full onsite days (up to 8h/day)
  • Executive-level materials in plain English
  • CEO Tactical Guide to IT (handbook) — free
  • Prioritized 90-day plan & 12-month outline
  • Optional: summary briefing for your leadership team
CEO IT Advisor: On-Demand Monthly Retainer

Flexible, ongoing support for CEOs who need IT clarity without a 2-day commitment. Example: Saved a client $10,000 USD by renegotiating a vendor contract.

  • Virtual environment assessment (initial 60-min call)
  • Monthly strategy sessions (1–2 calls, 60 min each)
  • Unlimited email/portal support, priority response
  • Quarterly 90-day plan updates
  • Optional: Virtual deep-dive ($995 USD) or onsite day ($3,995 USD)
Explore On-Demand
Boot Camp vs. Full IT Audit
CEO Boot Camp (this page) Full Technical IT Audit
Time to Value 2 days, executive clarity fast 4–8 weeks, deep technical detail
Focus Leadership understanding, cost clarity, 90-day plan Controls, configs, compliance, risk deep-dive
Who Attends CEO + leadership (IT optional touchpoints) IT staff, engineers, auditors
Typical Investment $7,995 $10,000–$20,000+
Best When You need clarity and decisions now You need evidence for compliance or a full technical baseline
Frequently Asked Questions

Yes. CEO Boot Camp is a 2-day consecutive, onsite engagement to maximize effectiveness and immersion.

Just a short confidential intake (10–15 minutes). We tailor the agenda to your environment.

We generally recommend that your current IT lead or team do not attend the core Boot Camp sessions.

This program is designed to give you a completely unfiltered, confidential environment — a space where you can voice every concern, ask uncomfortable questions, and test assumptions without worrying about internal dynamics or putting anyone on the defensive.

Many CEOs seek the Boot Camp precisely because their IT staff or provider has struggled to explain things clearly or justify costs in business terms. The 2-day session is your chance to get clarity without translation layers, then return to your organization with confidence and a plan.

How we include IT constructively:
  • Optional 15–30-minute fact-check touchpoints during Day 1–2 if specific data is needed (e.g., license counts, vendor terms).
  • Post-camp alignment: after Day 2, we can brief your IT lead or provider separately, or run a joint session to translate outcomes and next steps.
This approach keeps the CEO’s learning environment candid and free of influence — while still ensuring your IT team is constructively engaged once you’re ready to act.

Yes. Private and access-controlled. Nothing is shared without your explicit consent.

Ideal for SMBs with 10–250 employees or $1M–$50M revenue. Tailored to your stage.

Perfect. We’ll help you understand your setup, evaluate vendor performance, and manage outsourced IT effectively.

Yes—after you understand each concept in plain English. Then we map the industry term (e.g., SaaS) so you can follow future vendor/IT discussions confidently.

Yes! Our CEO IT Advisor: On-Demand Monthly Retainer offers flexible, virtual support with a 60-minute environment assessment, monthly strategy sessions, and unlimited email support. Learn more.
Pricing (All Prices in USD)
All prices are in USD. Travel & accommodations billed at cost. Value & ROI: Clients typically save 10–20% on IT budgets within 6 months.
Why It’s Worth It: Compared to $10,000–$20,000 USD for a full IT audit, the CEO Boot Camp delivers targeted, executive-level clarity and actionable plans in just 2 days.
CEO Boot Camp — Onsite (2 Days)
$7,995 USD
Two consecutive days, up to 8h/day
  • Pre-work intake & tailoring
  • Executive-level materials (plain English)
  • 90-day action plan + 12-month outline
  • CEO Tactical Guide to IT (included, free)
Optional additional on-site day (by request): $3,995 USD
Book Now
Add-Ons
  • CEO IT Advisor On-Demand (Monthly): from $1,495/mo USD
  • After-hours/weekend delivery: +20% ($1,599 USD)
  • Multi-site same trip: $2,000/site USD
  • Deep-dive document/data review: $2,500 USD
  • Board/Investor presentation package: $1,950 USD
Travel & Expenses

Billed at cost with receipts. Figures below are guidance only; we’ll confirm specifics during scoping.

Policy
  • Air: economy flexible by default; premium/business on request.
  • Hotel: business-class (3–4★) near your site.
  • Ground: ride-share/taxi or rental as appropriate.
  • Meals & incidentals: reasonable & customary.
  • Pre-approval provided for any atypical costs.
Typical Ranges (Guidance Only)
RegionAirfare (rt)Hotel / nightGround / day
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Actuals vary by season, route, and city.
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Note: CEO Boot Camp is onsite-only and delivered over 2 consecutive days. All prices on this page are listed in USD.
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