Executive IT Strategy Club
for CEOs & SMB Leaders

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.

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 ~50 staff). Larger environments priced by scope.

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.

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.

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.

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.

A focused review of your cybersecurity posture – controls, governance, backup, access, vendors – with a clear “state of play” and prioritized risk list.

• ✔Assess gaps against practical SMB best practices
• ✔Highlight critical, high and medium risks
• ✔Short, board-ready summary and next steps

From $3,950 USD, based on size and complexity.

A working session to turn your current IT spend and plans into a simple, multi-year budget and forecast that fits your growth plans.

• ✔Clarify run-rate vs. projects vs. one-offs
• ✔Align spend with hiring and revenue plans
• ✔Output: simple budget you can use with finance

From $2,950 USD, virtual half-day or full-day.

A targeted look at overlapping vendors, tools and licenses to uncover simplification and savings opportunities without hurting resilience.

• ✔Identify redundancies across tools & platforms
• ✔Outline consolidation options and trade-offs
• ✔Highlight quick wins and renewal timing

From $3,250 USD, depending on vendor/tool count.

A practical DR/BC blueprint tuned to your size – what you’ll do, in what order, and with what tooling when something serious fails.

• ✔Clarify RPO/RTO targets and what’s realistic
• ✔Map systems, dependencies and manual workarounds
• ✔Deliver a usable DR/BC runbook for leadership

From $2,950 USD, based on environment scope.

A structured session to align your IT roadmap (infrastructure, cloud, security, data) with your actual growth and change plans.

• ✔Translate business strategy into IT priorities
• ✔Sequence projects and investments sensibly
• ✔Produce a 12–24 month roadmap you can share

From $3,450 USD, virtual session with follow-up summary.

Independent support on major vendor deals or renewals – translating proposals, flagging traps, and helping you negotiate from a stronger position.

• ✔Review proposals and SLAs in plain English
• ✔Highlight key risks, lock-ins and gotchas
• ✔Provide talking points for negotiation

From $2,250 USD per major contract or renewal.

A recurring “light audit” each quarter to keep leadership and boards confident that IT risk, vendors and controls are being watched and improved.

• ✔Quarterly review of risk, incidents and controls
• ✔Track progress on agreed actions and gaps
• ✔Provide a brief, board-friendly update template

From $2,950 USD / quarter, depending on scope and regulation.

A practical session for your leadership or management team covering cyber risk, common attack paths, and what “reasonable steps” look like for an SMB.

• ✔Explain ransomware, phishing & vendor risk in plain English
• ✔Clarify who does what during an incident
• ✔Give leaders simple habits to reduce risk

From $1,950 USD, virtual or on-site (plus travel).