Executive IT Trusted Advisor — discreet, CEO-only monthly advisory. Save 25% for 12 months if enrolled before December 31, 2025 (Billing in USD)
Senior Advisory • Not a Helpdesk

Executive IT Trusted Advisor

A monthly, plain-English advisory service for SMB CEOs. 2× 30-minute booked calls per month, plus unlimited quick questions via email/Teams/Signal. Discreet, CEO-only counsel that helps you confidently counter questions and objections — in day-to-day operations and in the boardroom. No contract.

Founded 2004 · Vendor-neutral · Canada-based
Limited-Time 25% OFF
Built for the busy CEO
  • 2× 30-min booked calls / month
  • Unlimited quick questions by email/Teams/Signal
  • Discreet CEO-only advisory (share internally as you choose)
  • Vendor quote sanity-checks & red-flag lists
  • Board-ready one-page brief each month
Promotional Pricing (No Contract)
$1,895 USD $1,421 USD /mo
Save 25% for 12 months · Offer ends December 31, 2025
Book a 20-min Intro
Emergency access: one emergency session per month with 1–2 hour response SLA. Additional emergencies billed at $450/hour.

This is not an IT Helpdesk

We don’t reset passwords or roll out endpoints. We advise the person who signs — the CEO — so you can navigate proposals, risk, budgets, cyber insurance, and compliance with confidence.

Helpdesk / MSPExecutive IT Trusted Advisor
Ticket queues, break/fix, toolingDecisions, risk, ROI, board readiness
SLAs for incidentsBooked calls + same-day advice for strategy questions
Tool/vendor operationsVendor-neutral sanity-checks & negotiations
Tech metricsBusiness outcomes & narrative

What you get every month

  • 2× 30-minute booked calls (CEO-only)
  • Unlimited quick questions (≤10 min) via email/Teams/Signal
  • 1× board-ready one-page brief (risks, spend, initiatives)
  • Proposal & quote reviews with plain-English recommendations
  • Quarterly priorities alignment & roadmap sanity-check
All phone calls must be booked and scheduled in advance.

Where CEOs tap us most

Vendor sanity-checks

ERP, VoIP, EDR, MDR, cloud, “AI” add-ons — we cut through jargon, pressure tactics, and gotchas before you sign.

Board & lender prep

One-page briefs and confident talking points. Turn “tech risk” into measurable, funded action.

Cost & risk trade-offs

What’s the ROI? What’s the exposure? We frame decisions in business terms, not acronyms.

Simple monthly subscription

No contract · Cancel anytime · Promotional rate locked for 12 months

Limited-Time 25% OFF

Executive IT Trusted Advisor

Senior advisory for 1:1 CEO support
$1,895 USD $1,421 USD /mo
Save 25% for 12 months · Offer ends December 31, 2025
  • 2× 30-minute booked calls
  • Unlimited quick questions (≤10 min)
  • Monthly board-ready brief
  • Proposal/quote reviews & red-flag list
  • Roadmap & budget alignment
Book Intro Call
Calls must be scheduled in advance. One emergency session/month with 1–2 hr response; additional emergencies at $450/hour.

Other Services Available

  • 2-Day Executive CEO IT Bootcamp — intensive strategy, risk, and decision framework for CEOs
  • IT Cost Optimization Audit (Virtual) — spend baseline, vendor rationalization, quick wins
  • IT Cost Optimization Audit (2-Day On-Site) — interviews, on-site discovery, prioritized savings plan
  • Boardroom Representation — available with minimum 2 weeks’ notice · $3,500 USD per instance + travel & accommodations (capped at $750/day)
Ask about scheduling and pricing for Bootcamps, Audits, and Boardroom Representation (virtual or on-site).

How it works

1
Kickoff & context

We capture your goals, spend, vendors, risks, and politics — fast.

2
Booked CEO calls

Two 30-minute sessions monthly, scheduled in advance to fit your calendar.

3
Quick questions, fast

Unlimited quick questions via email/Teams/Signal (≤10 min each).

4
Board-ready briefs

One concise page each month — risks, spend, decisions, talking points.

A discreet, CEO-only advisory

This service is designed entirely to support CEOs only. The information we provide them can be relayed to their CFOs, COOs, IT Managers, MSPs, or other stakeholders as they choose. It’s structured for the CEO’s utmost confidence without inside pressures — a truly open-door consult.

  • CEO-first, confidential guidance
  • Neutral translation between business and technology
  • Clear, counter-ready talking points for board or exec peers

What leaders say

“They turn techno-babble into bottom-line choices. We’ve never gone into a board meeting more prepared.”

— CEO, 120-employee manufacturer

“Every quote gets a red-flag pass before I sign. The savings and avoided mistakes paid for the service.”

— Owner, multi-site services firm

Frequently asked questions

No. This is an executive advisory subscription for the CEO. We don’t reset passwords or manage endpoints. We translate tech into business, de-risk decisions, and prepare you for vendor and board conversations.

You receive 2× 30-minute booked calls per month and unlimited quick questions (the kind that take ~10 minutes or less) via email/Teams/Signal. Emergencies receive a call-back within 1–2 hours (limited to one emergency session per month); additional emergencies are billed at $450/hour.

This is a discreet service designed entirely to support CEOs only. The information we provide can be relayed by the CEO to a CFO, COO, IT Manager, MSP, or other stakeholders as they see fit.

Boardroom representation is available with a minimum 2 weeks’ notice and is billed at $3,500 USD per instance plus travel & accommodations (capped at $750 USD per day). Most CEOs find they’re fully equipped after our preparation sessions.

Yes, while this is a virtual service, on-site presence can be arranged for a flat-rate fee of $3,500 USD per day plus travel and accommodation expenses (capped at $750 per day).

No contract. Month-to-month billing. New clients enjoy a 25% promotional savings for their first 12 months if enrolled before December 31, 2025.

Make confident IT decisions — every week

Discreet CEO-only counsel, vendor sanity-checks, and board-ready clarity — on your schedule.

Contact IT Support 101 Inc.