The Executive AI Playbook

Artificial intelligence is no longer experimental. It is reshaping customer trust, operating models, and competitive advantage faster than most leadership teams are prepared for.

This white paper provides a practical, executive-level framework for governing AI, aligning it to business outcomes, and moving from isolated pilots to durable impact.

Download the White Paper

Why This Paper Exists

AI failure is rarely technical. It is almost always a leadership and execution problem.

Ambition Without Ownership

AI is frequently declared a strategic priority, yet executive ownership, decision rights, and success metrics remain unclear.

Without explicit accountability at the C-suite level, initiatives fragment into pilots that never compound into enterprise value.

Leadership Risk Has Changed

AI introduces ethical, regulatory, reputational, and customer-trust risks that traditional governance models were not designed to manage.

Systems that learn and adapt require new forms of oversight and decision-making.

Delay Is No Longer Neutral

Inaction carries cost. Early movers benefit from compounding advantages in data, learning velocity, and execution maturity.

Waiting for clarity often results in falling behind faster than anticipated.

What You’ll Learn

An execution framework for leaders navigating irreversible change.

The Three Forcing Functions

How AI fundamentally alters leadership decision cycles, competitive dynamics, and accountability models.

Pitfalls: Shiny Objects & Black Boxes

Why organizations chase tools without strategy and deploy systems they cannot explain, govern, or trust.

The Execution Framework

A structured model connecting AI initiatives to business outcomes and executive ownership.

Governance & Guardrails

Practical guidance for managing risk, ethics, compliance, and decision rights at scale.

A Phased Roadmap

How organizations move from pilots to repeatable, enterprise-grade AI capability.

Leadership Behaviors

The executive habits required to sustain advantage in AI-driven organizations.

The Collaboration

Authors and contributors to the Executive AI Playbook.

Bill Sanders

Alignment & Transition

Bill Sanders, with 20 years of collaborating closely with C-suite leaders, specializes in aligning AI strategies with business goals. His work has guided Fortune 500 executives through technology transformations. As a transition strategist, Bill's insights in this paper offer practical frameworks for AI leadership.

Andrew Stevens

CTO, CISO, Executive Leader

Andrew Stevens is an executive technology leader and entrepreneur who has scaled AI and cloud businesses from inception through acquisition. Operating across Europe and the US, he combines deep expertise in cloud architecture, machine learning, and security with a track record of building and leading high-performing teams across fintech, media, gaming, and travel.

Olivia Storelli

CEO & AI Strategy

Olivia is the CEO and Co-founder of Sakura Sky, where she helps corporations turn cloud and AI investment into strategic assets. With over 20 years of experience, she combines the strategic discipline of scaling complex businesses across multiple continents with the deep technical expertise required to deliver secure, private, and well-governed technology solutions.

Jennifer Capo

Program Development & Facilitator

Jennifer Capo designs executive programs to navigate AI adoption. Her facilitation expertise ensures this paper's insights are clear and practical, drawing from her partnership role with Roebling Strauss & Sakura Sky's AI Executive Accelerator.

From Strategy to Action

A companion experience designed to turn executive intent into decisive execution.

The custom Executive AI Accelerator program translates the frameworks outlined in this white paper into focused executive action.

This program compresses months of internal debate into a structured, decision-driven engagement aligned to your organization's strategy, governance requirements, and operating reality.

Explore the Executive AI Accelerator