Media &
Intelligence.

Building AI Fluency for Executive Leaders

Through The Context Window and emerging executive education programs, we develop the AI fluency business leaders need to drive transformation, manage risk, and capture competitive advantage.

1,000+
Executive Subscribers
Building AI fluency through weekly intelligence

Path to AI Fluency

A structured journey from AI awareness to confident leadership, designed for executives navigating transformation

Stage 1

AI Awareness

Understanding AI's strategic implications

Stage 2

Conceptual Understanding

Grasping frameworks and decision criteria

Stage 3

Strategic Application

Making informed investment decisions

Stage 4

Confident Leadership

Leading AI transformation with clarity

Artificial intelligence is reshaping competitive dynamics across every industry. Yet most business leaders lack the fluency to evaluate AI opportunities, assess risks, or make informed strategic decisions. The gap between technical complexity and executive understanding creates vulnerability—organizations either move too slowly and lose ground, or adopt AI recklessly and expose themselves to compliance, security, and reputational risks.

AI fluency (also called artificial intelligence fluency) is the conceptual understanding, strategic frameworks, and decision-making capabilities that enable executives to lead AI transformation confidently. Unlike AI literacy, which focuses on basic awareness, AI fluency empowers business leaders to evaluate AI opportunities, assess risks, design governance frameworks, and make multi-million dollar technology investment decisions. It's knowing which questions to ask, which risks to prioritize, and which opportunities to pursue—without requiring technical expertise in machine learning or data science.

That's why we built The Context Window—a weekly intelligence briefing that translates AI developments into strategic insights business leaders can actually use. What began as a newsletter is evolving into a comprehensive executive education platform, combining written intelligence, multimedia content, interactive workshops, and premium advisory services designed to accelerate AI fluency at the leadership level.

The Context Window

Executive AI Intelligence

1,000+
Executive Subscribers
Independent
No Vendor Bias

Every Sunday, over 1,000 business leaders receive The Context Window—a curated intelligence briefing that distills the week's most significant AI developments into actionable insights. Each issue delivers strategic analysis across five key dimensions.

Enterprise AI

Strategic implementation, organizational transformation, executive decision-making

AI Governance

Frameworks, policies, risk management, compliance

AI Tools

Enterprise evaluation, vendor assessment, use case analysis

Strategic Analysis

Competitive implications, industry trends, paradigm shifts

Why Executives Subscribe

Strategic depth
Analysis that informs board-level decisions
Executive accessibility
Clear explanations without jargon
Practical application
Frameworks you can implement Monday
Independent perspective
No vendor bias or conflicts

Recent Featured Analysis

  • •Three Strategic Shifts in Enterprise AI for 2026 (a16z + Google Cloud insights)
  • •AI Agent Capabilities: Current State and Business Readiness Assessment
  • •EU AI Act Compliance Timeline: What US Companies Need to Know
  • •GEO Strategy: Optimizing for AI-Powered Search and Recommendations
  • •The Hidden Cost of Shadow AI in Regulated Industries

The Future: Executive AI Fluency Platform

While The Context Window newsletter serves as our foundation, we're building a comprehensive executive education platform that develops AI fluency through multiple formats and engagement models.

Video Intelligence Series

Visual explanations of complex AI concepts, tool demonstrations, case study analyses, and expert interviews. Designed for executives who prefer video learning or want to share insights with their leadership teams.

Executive Podcast

Deep-dive conversations with AI leaders, case study explorations, and strategic analysis in audio format. Perfect for commutes, workouts, or any time you want to build AI fluency on the go.

Interactive Workshops

Live learning experiences focused on specific AI fluency domains: governance framework design, vendor evaluation, pilot program structuring, ROI measurement, and change management.

Executive Summits

Invitation-only gatherings for senior leaders navigating AI transformation. Share experiences, discuss challenges, and learn from peers who are solving similar problems.

Subscription Tiers & Engagement Models

The Context Window

Free Newsletter

Weekly executive intelligence briefing delivered every Sunday. Strategic analysis, case studies, implementation frameworks, and emerging capability assessments.

  • Weekly strategic briefing
  • Enterprise AI case studies
  • Risk & compliance intelligence
  • Tool evaluation & vendor assessment
  • Implementation frameworks
Coming Soon

Premium Intelligence

Coming Soon

Enhanced research, exclusive case studies, early access to workshops, and private community forum. For executives who need deeper analysis and peer connection.

  • Enhanced research reports
  • Exclusive case studies
  • Early workshop access
  • Private community forum
  • Priority support

Executive Advisory

Custom Engagement

One-on-one coaching, strategic advisory, and hands-on support for leaders driving AI initiatives. Custom engagements designed around your specific challenges.

  • One-on-one executive coaching
  • Strategic advisory services
  • Hands-on implementation support
  • Custom governance frameworks
  • Direct team access

Our Approach to AI Fluency Development

Conceptual Understanding Over Technical Depth

AI fluency doesn't require understanding neural network architectures or training algorithms. It requires understanding business applications, risk implications, competitive dynamics, and strategic decision frameworks. We focus on the concepts that matter for executive decision-making.

Real-World Case Studies with Quantifiable Outcomes

Every strategic insight is grounded in real implementations with measurable results. We don't traffic in hypotheticals—we analyze what actually worked, what failed, and why.

Independent Analysis Without Vendor Bias

We don't accept sponsorships that compromise editorial integrity. We don't promote tools we haven't tested. We don't recommend vendors who haven't demonstrated enterprise readiness. Our only incentive is helping you make better decisions.

Strategic Frameworks Over Tactical Tips

We provide decision-making frameworks, evaluation criteria, and strategic methodologies—not productivity hacks or tool tips. Our content is designed for leaders making multi-million dollar decisions, not individual contributors optimizing workflows.

From Intelligence to Implementation

Many of our consulting engagements begin with a newsletter subscriber reaching out for strategic guidance. If you're facing complex AI governance challenges, evaluating enterprise AI investments, or leading organizational AI transformation, we provide hands-on advisory support.

AI Governance & Advisory

Framework design, policy development, risk management

Regulated Industries

Compliance-focused AI adoption for life sciences, healthcare, finance

Digital Professional Services

Technology due diligence, system implementation, vendor evaluation

PE Portfolio Optimization

Buy-side diligence, post-acquisition integration, value creation

Build AI Fluency.
Lead with Confidence.

Subscribe to The Context Window and join over 1,000 business leaders who are making smarter AI decisions every week.

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