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    Strategic Advisory

    Strategic AI Advisory for Mid-Market CEOs

    Shawn Moore, Founder of AI Savvy CEO
    Shawn Moore
    Updated · 11 min read

    Most AI advisory is built for Fortune 500 CIOs or venture-funded startups. This is built for the CEO of a $10M–$1B company who needs to make capital allocation decisions on AI in the next two quarters and have a defensible answer for the board. No frameworks built in a vacuum, no transformation theater — direct work, delivered personally by Shawn Moore, on the actual decisions in front of you.

    Book a Strategic Call Read the readiness framework

    Who this is for

    • CEOs of $10M–$1B companies evaluating AI investment for the first time, or recovering from a stalled pilot portfolio.
    • PE-backed leadership teams under pressure to show AI traction without sacrificing operating discipline.
    • Founder-CEOs whose board is asking 'what's our AI strategy?' and the answer needs to land in writing.
    • CFOs and COOs who are co-sponsoring AI initiatives and need a partner the executive team will actually listen to.

    What you get

    • A scored AI Readiness Assessment across the six pillars (strategy, data, infrastructure, governance, talent, culture) with a sequenced remediation plan.
    • A capital allocation framework that maps every candidate AI investment to build, buy, or wait — with three-year TCO modeling.
    • A board-ready AI strategy memo: positioning, priorities, governance posture, and the two-year roadmap, in language a non-technical board can defend.
    • Vendor selection support for the two-to-four AI investments you actually move forward with — including reference call scripts and contract red flags.
    • Direct access between sessions for the inevitable curveballs (a vendor pitch, a board question, a competitor announcement).

    Methodology

    Diagnose before prescribing

    Engagements start with a structured diagnostic of your current AI posture — anchored in the six-pillar AI readiness framework, not a survey. The output is a written assessment you can hand to anyone on the board and they will understand exactly where you stand and why.

    Allocate capital like a portfolio

    Every candidate AI initiative is plotted using the build vs buy vs wait matrix against strategic differentiation and time-to-value, then stress-tested against three-year TCO. The output is a ranked portfolio with named owners, reconsideration triggers, and a clear answer for the things you are choosing not to fund.

    Build the governance scaffold first

    Most mid-market AI failures are governance failures, not technology failures — the four failure modes are well documented. We design the lightweight oversight model — accountable owners, escalation paths, kill criteria — before the first dollar of pilot capital is committed.

    Stay through execution, not just strategy

    The strategy memo is the start, not the deliverable. Ongoing engagements include monthly working sessions through the first two-to-three implementations, when most of the real decisions get made and most consultants have already moved on.

    Engagement model

    Diagnostic Sprint
    Six weeks. Readiness assessment, capital allocation framework, and board-ready strategy memo. Fixed scope, fixed fee.
    Ongoing Advisory
    Twelve-month retainer. Monthly working sessions with the executive team plus on-demand access for vendor decisions and board prep.
    Board Engagement
    One-time board working session: state of AI in your industry, your readiness, the recommended posture. Two hours, no slides.
    Geographic scope
    United States and Canada. Hybrid delivery — quarterly on-site working sessions, monthly virtual.
    BEGIN WITH 

    Strategy Programs

    Three phased AI business audit engagements designed to help leadership teams understand where AI will affect revenue, operations, production, customer experience, and product development — then prioritize what to fix, automate, protect, or reinvent first. Each engagement builds on the previous one. Start with visibility and revenue, expand into operating systems, then move into full enterprise-level AI opportunity mapping.

    Phase 1

    AI Growth Upgrade

    $6,995one-time
    AI Search + Sales & Marketing Readiness

    A focused upgrade for companies that want to understand how AI is already changing customer discovery, search visibility, content, lead generation, and sales enablement.

    • AI search visibility review across Google AI Overviews, ChatGPT, Perplexity, and other answer engines
    • AEO/GEO readiness audit for brand, products, services, and executive expertise
    • SEO and entity-positioning review for AI grounding
    • Website and landing page messaging review
    • Sales and marketing content gap analysis
    • AI-assisted content improvement recommendations
    • Lead-generation and conversion opportunity review
    • Citation, authority, and mention acquisition plan
    • Priority action list for the first 30–60 days
    • Creation of an implementation plan and budget.
    Best for

    Businesses that want to improve AI-era discoverability, strengthen sales and marketing performance, and prepare their website and content for AI-driven buyer journeys.

    Improve AI Visibility
     POPULAR
    Phase 2

    AI Business Systems Audit

    $9,995one-time
    Sales, Marketing, CRM, Operations + Automation Roadmap

    Our most popular engagement. A deeper audit of the business systems that turn attention into revenue, with a focus on practical AI adoption across sales, marketing, operations, and customer workflows.

    • Everything in Phase 1
    • CRM and marketing automation audit
    • Lead-to-revenue workflow review
    • GA4, GTM, tracking, and attribution audit
    • Sales process and follow-up system review
    • Email, nurture, and customer communication workflow review
    • AI automation opportunity map for sales, marketing, and admin tasks
    • Competitive benchmarking for AI visibility and digital positioning
    • Internal content and knowledge-base opportunity review
    • 6-month AI, SEO, content, and automation roadmap
    • Prioritized quick wins, system gaps, and implementation sequence
    • Creation of an implementation plan and budget.
    Best for

    Companies that want a practical AI roadmap across revenue systems, marketing operations, CRM, automation, and customer acquisition workflows.

    Optimize Revenue Systems
    Flagship
    Phase 3

    Full AI Business Audit

    $19,995one-time
    Enterprise-Wide AI Opportunity Map: Sales, Marketing, Production, Operations + Product Development

    Our flagship engagement. A comprehensive AI audit of the business areas most likely to be changed by artificial intelligence: sales, marketing, production, operations, customer experience, internal knowledge, and future product or service development.

    • Everything in Phase 1 and Phase 2
    • Executive AI readiness assessment
    • Product and service positioning audit
    • Production and delivery workflow review
    • Operations and administrative process audit
    • Customer experience and support workflow review
    • AI agent and chatbot opportunity map
    • Internal knowledge, documentation, and training systems review
    • Product development and service innovation opportunity review
    • Build, buy, or automate recommendation framework
    • Risk, governance, privacy, and brand-safety considerations
    • Vendor, tool, and platform opportunity review
    • Executive workshop
    • 12-month AI business transformation roadmap
    • Creation of an implementation plan and budget.
    Best for

    Leadership teams that want a board-level view of how AI will affect the entire business and a clear, sequenced roadmap for adoption across departments.

    Map AI Opportunities

    Frequently asked questions

    What does AI strategy advisory for CEOs include?

    A 1:1 engagement between Shawn Moore and a company's CEO (plus optionally board or executive team) covering AI readiness assessment, use case prioritization, 90-day execution blueprint, governance design, and measurable outcomes. Engagements run 90 days to 12 months, begin with a complimentary strategic call, and are delivered virtually across the US and Canada.

    How much does AI strategy advisory cost?

    AI advisory for CEOs typically ranges from $7,500–$25,000 for a fixed-scope readiness assessment, $10,000–$40,000 per month for ongoing fractional advisory, and $50,000–$250,000+ for multi-quarter transformation engagements. AI Savvy CEO sits in the mid-market band, priced 40–70% below Big-4 and McKinsey equivalents.

    How is AI Savvy CEO different from big consulting firms?

    AI Savvy CEO is a 1:1 operator-CEO practice led by Shawn Moore, who has run two companies for 30 years across digital strategy and AI. Unlike Big-4 or McKinsey, engagements are delivered by Shawn personally (not a rotating team), priced for mid-market budgets, and grounded in operator P&L experience — not academic frameworks.

    What is an AI readiness assessment?

    A structured 2–4 week diagnostic that benchmarks AI maturity across six pillars (strategy, data, infrastructure, governance, talent, culture), identifies high-ROI use cases, maps competitive positioning, and produces a prioritized 90-day roadmap. It replaces open-ended experimentation with evidence-based decisions tied to revenue and margin.

    What is the 90-day AI blueprint?

    A CEO-facing execution plan sequencing AI initiatives across three 30-day phases: discovery and audit (weeks 1–4), piloting two to three prioritized use cases (weeks 5–8), and scaling with governance, metrics, and change management (weeks 9–12). It targets a measurable business outcome, not a technology demo.

    Who is the ideal client for strategic advisory?

    CEOs of mid-market companies ($10M–$250M revenue) in the US or Canada who need AI strategy personally delivered — not delegated to a consulting firm. Typical clients are private or founder-led companies navigating AI-driven competitive pressure in professional services, finance, healthcare, technology, and family-owned enterprises.

    How long does a typical advisory engagement run?

    Engagements run 90 days for a fixed-scope readiness-plus-blueprint deliverable, 6 months for implementation-phase support, or 12 months for ongoing fractional Chief AI Officer coverage. Most CEOs start with a 90-day engagement and extend to a fractional retainer after the initial blueprint is executed.

    Do you work with Canadian companies?

    Yes. Shawn Moore is Canadian, based in Vancouver, BC, and AI Savvy CEO operates in both the US (Lahaina, HI entity) and Canada (Vancouver operating address). Canadian engagements address PIPEDA, OSFI, provincial privacy laws, and CAD pricing. US engagements address NIST AI RMF, state privacy, and SEC disclosure requirements.

    Related insights

    Methodology

    The AI Savvy Readiness Framework

    The six-pillar assessment used in every diagnostic sprint. Score strategy, data, infrastructure, governance, talent, and culture before committing capital.

    The AI Savvy Readiness Framework: Read the full insight     Research

    Why Enterprise AI Pilots Fail

    The four-failure taxonomy that drives our pilot portfolio review. Diagnose before you fund the next experiment.

    Why Enterprise AI Pilots Fail: Read the full insight     Methodology

    The Build vs Buy vs Wait Matrix

    The capital allocation framework behind our vendor selection support. Plot every AI investment against differentiation and urgency.

    The Build vs Buy vs Wait Matrix: Read the full insight

    Related services & resources

    About Shawn

    About Shawn Moore, 30-year operator-CEO

    Three decades running P&L across digital strategy and AI. Why CEOs hire Shawn directly instead of a Big-4 team.

    About Shawn Moore, 30-year operator-CEO: Read the full insight     Keynote Speaking

    Also available for keynote speaking

    Bring the same frameworks to your next conference, board offsite, or PE portfolio convening.

    Also available for keynote speaking: Read the full insight

    Ready to start the conversation?

    Thirty minutes. No deck. We work the actual problem and you leave with a defensible next step.

    Book a Strategic Call
    Book a Strategic Call