CEO's Guide to Building Your AI Strategy Roadmap

A picture of Richard Casemore

Richard Casemore - @skarard

October 28, 2025

Beyond Point Solutions

Most organizations have AI experiments scattered across departments. Sales has a tool. Marketing tried something. IT built a prototype. But there's no coherent strategy.

This fragmentation wastes resources and misses compounding benefits. It's time for a real roadmap.

The Strategy Framework

Four Horizons of AI Adoption

Horizon 1: Foundation (Now - 6 months)

  • Deploy proven AI tools across functions
  • Build data infrastructure for AI
  • Develop AI governance basics
  • Create initial training programs

Horizon 2: Integration (6-18 months)

  • Connect AI systems across functions
  • Develop proprietary AI capabilities
  • Build AI competency at scale
  • Establish measurement frameworks

Horizon 3: Transformation (18-36 months)

  • Reimagine core processes around AI
  • Develop AI-native products/services
  • Build competitive moats
  • Create AI-enabled business models

Horizon 4: Leadership (36+ months)

  • Industry-defining AI capabilities
  • AI as core competitive advantage
  • Continuous innovation engine
  • Ecosystem and platform effects

Month 1: Assessment

Current State Inventory

Document:

  • All AI initiatives (official and shadow)
  • Data assets and quality
  • Technical infrastructure
  • Talent and skills
  • Vendor relationships
  • Governance maturity

Competitive Analysis

Understand:

  • What are competitors deploying?
  • What are industry leaders doing?
  • What disruption risks exist?
  • Where are opportunities to lead?

Gap Analysis

Identify:

  • Technology gaps
  • Skill gaps
  • Data gaps
  • Process gaps
  • Governance gaps

Month 2: Vision and Priorities

Strategic Questions

Engage your leadership team:

  1. Where will AI create the most value for us specifically?
  2. What's our appetite for AI risk?
  3. Build, buy, or partner?
  4. How fast do we need to move?

Priority Matrix

Score opportunities on:

  • Business impact (revenue, cost, risk)
  • Feasibility (data, technology, talent)
  • Strategic alignment
  • Competitive urgency

Define 3-5 Strategic Bets

These should be:

  • Material to business results
  • Achievable in 18 months
  • Aligned with corporate strategy
  • Resourceable

Month 3: Organizational Design

Governance Structure

Establish:

  • AI Steering Committee (C-suite)
  • AI Ethics Review Board
  • AI Center of Excellence
  • Business unit AI leads

Reporting and Accountability

Define:

  • Who owns AI strategy?
  • Who approves investments?
  • Who manages risk?
  • Who measures outcomes?

Talent Strategy

Plan for:

  • Key hires (vs. develop internally)
  • Training programs
  • External partnerships
  • Retention of AI talent

Month 4: Roadmap Development

90-Day Quick Wins

Identify 3-5 initiatives that:

  • Can launch within 90 days
  • Demonstrate visible value
  • Build organizational momentum
  • Don't require major infrastructure

Year 1 Foundations

Plan for:

  • Data infrastructure investments
  • Key platform decisions
  • Governance implementation
  • Training rollout

Year 2-3 Transformation

Outline:

  • Major transformation initiatives
  • Capability building investments
  • Organizational evolution
  • Success metrics

Month 5-6: Execution Planning

Investment Case

Build a compelling case covering:

  • Expected returns by initiative
  • Required investments
  • Risk assessment
  • Competitive implications

Resource Allocation

Determine:

  • Budget by initiative
  • Headcount requirements
  • Technology investments
  • External partnerships

Communication Plan

Prepare:

  • Board communication
  • Employee communication
  • Customer/market messaging
  • Investor positioning

Governance Essentials

AI Ethics Principles

Document your position on:

  • Transparency in AI use
  • Fairness and bias mitigation
  • Privacy and data use
  • Human oversight requirements
  • Accountability for AI decisions

Risk Management

Establish processes for:

  • AI risk assessment
  • Model validation
  • Incident response
  • Regulatory compliance

Metrics and Accountability

Track:

  • Business outcomes by initiative
  • AI adoption rates
  • Risk indicators
  • Return on AI investment

Common CEO Mistakes

Under-investing: AI requires significant commitment to reach value Over-centralizing: Business ownership drives adoption Ignoring culture: Technology without change management fails Moving too slowly: Competitive windows close Chasing hype: Focus on your specific value creation

The Board Conversation

Be prepared to discuss:

  • Strategic rationale for AI investments
  • Risk management approach
  • Competitive positioning
  • Talent strategy
  • Governance framework
  • Success metrics

Measuring Success

Leading Indicators

  • AI literacy scores
  • Experiment velocity
  • Data quality metrics
  • Talent retention

Lagging Indicators

  • Revenue attributable to AI
  • Cost savings from automation
  • Customer experience improvements
  • Competitive position changes

The Bottom Line

AI strategy isn't about technology—it's about business transformation. The companies that win will be those that move deliberately but urgently, building capabilities that compound over time.

This roadmap gets you from fragmented experiments to coherent strategy. Start with the assessment. Build the vision. Execute with discipline.

The time for AI strategy is now. Not next quarter. Now.

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