Executive Advisory – Executive IT Strategy Club

What you get with Executive Advisory

Direct executive-level advisory

✔ Monthly 30-minute CEO/Executive strategy session
✔ Direct, unlimited email & Teams access for follow-up questions (asynchronous responses, typically within one business day)
✔ Translation of technical proposals into business impact
✔ Guidance on timing, phasing and prioritizing IT projects
✔ Support preparing for board, lender or investor conversations

Risk, readiness & vendor oversight

✔ Annual cybersecurity readiness and risk scorecard
✔ Up to 3 vendor quotes or projects reviewed monthly
✔ Virtual IT Cost Optimization Audit focused on major spend categories
✔ Guidance for completing cyber insurance questionnaires
✔ Recommendations you can hand to your IT team or MSP

When Executive Advisory is the right choice

Best for:

✔CEOs of companies with roughly 25–150 staff
✔Businesses with multiple IT vendors or critical systems
✔Organizations where IT is now a recurring board topic
✔Leaders who need recurring, neutral advice – not just content

Consider Full Executive Counsel instead if:

You want deeper involvement in budgeting and roadmapping.
You expect frequent, time-sensitive IT decisions.
You want quarterly board-ready reports and more active oversight.

Ask Whether Advisory or Counsel Fits Better

Optional executive add-ons

These are one-time or per-instance engagements that can be added to any membership tier. We’ll always recommend the smallest option that genuinely fits your situation. Advisory members frequently add Board / Lender IT Briefings and On-Site Strategy Days as needed.

IT Spend Baseline & Savings Map

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

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

From $3,250 USD (up to ~75–100 staff). Larger environments priced by scope.

Board / Lender IT Briefing (Virtual)

A focused, 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.

Incident / Ransomware Tabletop

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.

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). Available to Advisory & Counsel members first.

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.

Note: All add-ons are scoped and confirmed in writing before any work begins. No long-term commitment is required beyond your selected membership tier.

Have a neutral IT second opinion on speed-dial.

Executive Advisory gives you recurring access and structured time to think clearly about IT – before you sign, renew, or commit.

Book a Call About Executive Advisory