Executive IT Engagements – One-time, fixed-scope projects for CEOs. Vendor-neutral. Canada & USA.
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One-Time Executive Engagements • Vendor-Neutral • CEO-Focused

Executive IT Engagements
for CEOs & Owners

When you need a decisive, fixed-scope project – not another open-ended consulting retainer. These engagements are designed for CEOs who want clarity, savings, and a simple story they can stand behind.

View 5-Day CEO IT Bootcamp View Membership Tiers
All work is vendor-neutral. We do not resell hardware, software, or managed services.
When a one-time engagement fits better than a retainer:
  • ✔ You suspect overspend and want a one-time cost baseline & savings map.
  • ✔ Your board or lender wants a clear, independent IT story.
  • ✔ You want to test working together before a monthly advisory tier.
  • ✔ You need a tabletop or strategy day tied to a specific milestone.

You keep your MSP and IT team. We provide the map, the narrative, and the neutral second opinion.

Flagship: 5-Day CEO IT Bootcamp + Cost Optimization Review

On-site • CEO-only • Vendor-neutral

A discreet, CEO-only, 5-day on-site engagement that walks your environment, traces systems live, and converts complexity into a clear picture of risk, spend and priorities.

  • ✔5 full days on-site working directly with the CEO.
  • ✔Walk-through of server room, cloud footprint and key systems.
  • ✔IT Cost Optimization Review with 12-month savings roadmap.
  • ✔Board-ready executive brief you can take to your Chair or lender.
  • ✔90 days of post-engagement email/text support.

Best for CEOs who want deep clarity and a decisive reset in a single, focused week.

View Full Bootcamp Details Book Intro Call About 5-Day Bootcamp
5-Day CEO IT Bootcamp + Cost Review Flagship

$19,900 USD

Travel expenses capped at $1,500 USD per trip, pre-approved by you.

  • ✔CEO-only, confidential working sessions
  • ✔Live environment mapping & risk overview
  • ✔Concrete, dollar-linked savings opportunities
Learn More About the 5-Day Bootcamp
A concentrated option when you want a decisive reset on IT spend, risk and direction – quickly.

Other executive IT engagements

These can be booked as standalone projects or paired with a membership tier. All pricing is scoped and confirmed in writing before any work begins.

Discuss Which Engagement Fits
Ultimate CEO IT Handbook (1,000+ pages)

A comprehensive, plain-English 1,000+ page reference that gives CEOs and owners a complete, board-ready view of IT – strategy, risk, spend, vendors, cybersecurity and day-to-day realities.

  • ✔ Written for CEOs & owners – not IT people
  • ✔ Covers IT strategy, cost optimization, vendor games, cloud, cybersecurity & resilience
  • ✔ Includes checklists, vendor questions, and board/lender talking points

$495 USD one-time, digital edition.
Can be purchased standalone or alongside any membership tier.

View Handbook Details
IT Spend Baseline & Savings Map

One-time review of your current IT spend (MSP, licenses, connectivity, backup, security), with a clear visual of where the money goes and 3–5 concrete savings moves.

  • ✔Consolidate overlapping tools & services
  • ✔Spot “auto-renew” traps and surprise costs
  • ✔Map spend to business functions and risk

From $3,250 USD (up to ~50 staff). Larger environments priced by scope.

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Board / Lender IT Briefing (Virtual)

A plain-English briefing for your board or lender on current IT posture, key risks, and the short list of actions you are taking next.

  • ✔Pre-call to understand your priorities & politics
  • ✔Concise virtual briefing with Q&A
  • ✔Short written summary you can reuse

From $3,750 USD per briefing. On-site board sessions available by request.

View Briefing Details
Incident / Ransomware Tabletop

A scenario-based exercise with your leadership team to walk through who does what, in what order, and with what information when something goes wrong.

  • ✔Custom scenario tuned to your reality
  • ✔Facilitated 90–120 minute live session
  • ✔Gap list and next-step recommendations

From $2,750 USD per exercise (virtual). Hybrid and on-site options available.

View Tabletop Details
On-Site Strategy Day

One day on-site with your CEO, leadership team and key IT stakeholders to align roadmap, spend, and risk with your actual business plans.

  • ✔Pre-session call to shape the agenda
  • ✔Full-day working session on-site
  • ✔Written summary & 90-day action outline

From $5,250 USD plus travel (capped). Often paired with Advisory or Counsel.

View Strategy Day Details
Policy & Minimum Controls Pack

Lightweight tuning of core policies and minimum controls so you can demonstrate “reasonable steps” to staff, partners and insurers.

  • ✔Acceptable use & remote work policy tuning
  • ✔Backup / MFA / password baseline guidance
  • ✔Light customization for your environment

From $1,950 USD one-time, depending on complexity and number of locations.

View Pack Details

Note: You can book any of these as a standalone project, or bundle them with a membership tier (for example, an IT Spend Baseline & Savings Map followed by Growth Leadership or Executive Advisory).

Need a decisive, one-time push on IT?

Whether it’s the 5-Day CEO Bootcamp, a cost baseline, a board/lender briefing or a tabletop exercise, we’ll recommend the smallest engagement that genuinely fits your situation.

Book a Short Executive Intro Call

We’ll talk about where you are today, what’s keeping you up at night, and which path makes sense – if any.