CEO's Guide to Building Your AI Strategy Roadmap

Richard Casemore - @skarard
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:
- Where will AI create the most value for us specifically?
- What's our appetite for AI risk?
- Build, buy, or partner?
- 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.