The Executive AI Strategy Playbook
From AI hype to 1–3 high-ROI pilots in 90 days
A practical guide for mid-market leaders
Why This Playbook Exists
Right now, most mid-market companies are drowning in AI noise. Vendors everywhere. Scattered experiments. No clear owner. No ROI story.
This playbook cuts through the hype. It's a practical, step-by-step guide to identify your highest-ROI AI opportunities and execute 1–3 pilots in 90 days—without the typical $2M+ wasted spend on projects that never scale.
Focus on Impact
Start with business outcomes, not technology. Every recommendation ties back to measurable ROI.
90-Day Execution
No 12-month strategy documents. This is a tactical blueprint you can start implementing next week.
Mid-Market Focused
Built for companies with 50–5,000 employees. No enterprise complexity, no startup assumptions.
What You'll Get
- A shortlist of 3–5 AI opportunities worth real money in your business
- An Impact Triage scorecard to prioritize what matters most
- A 90-day pilot blueprint you can execute immediately
- A 1-page AI strategy snapshot for your leadership team
Use the interactive slides below to navigate through the playbook. Click the arrows, use your keyboard, or click the dots to jump to any section.
Use arrow keys or click to navigate
Ready to Execute Your 90-Day AI Pilot?
This playbook gives you the framework. If you want help identifying your highest-ROI opportunities and building a pilot plan tailored to your business, let's talk.
In 20 minutes, we'll have a conversation to understand your operations context, assess whether there's a fit for AI augmentation in your business, and determine if a 90-day Sprint makes sense for your situation.
Apply for Your 90-Day Sprint
Due to the hands-on nature of the Sprint, I work with a limited number of mid-market leaders each year. Tell me about your situation and I'll be in touch within 24 hours.
Current availability: Accepting applications for Q1 2026 engagements.
What to expect:
- ✓ 20-minute conversation to understand your context
- ✓ Quick assessment of AI opportunities in your operations
- ✓ Honest take on what's worth pursuing (and what's not)
- ✓ No obligation, just clarity on your next steps
Satisfaction guarantee: If the call doesn't provide value, I'll refund your time with actionable next steps at no charge.