PRACTITIONER · AUTHOR · COMMUNITY BUILDER

Making AI Transformation Stick.

25+ years leading enterprise modernization and delivery across Fortune 500 companies, Deloitte, Nike, Freddie Mac, and federal agencies including the IRS, CMS, VA, DoD, GSA, and HHS.

Based in Washington DC Metro. Founder of the Loudoun AiGile Network — 2,300+ practitioners. Speaker at 30+ global events. Author of The AI Leap.

DC Metro Fortune 500 Federal Agencies Big 4 Consulting Defense Sector

25+Years experience

30+Global speaking events

2,300+LAN community members

50US states visited

$100M+Platform scale

ABOUT TOBY

Practitioner first. Everything else follows.

Toby Rao is an AI transformation leader based in the Washington DC Metro, with 25+ years of enterprise modernization and delivery experience across Fortune 500 companies, Deloitte, Nike, Freddie Mac, and federal agencies including the IRS, CMS, VA, DoD, GSA, and HHS.

Founder of the Loudoun AiGile Network (LAN) — a community of 2,300+ practitioners navigating the intersection of Agile and AI. Speaker at 30+ global events. Author of The AI Leap.

Currently Global Director of R&D Operations and AI COE Lead at Exostar — a $100M FedRAMP Moderate SaaS platform serving Boeing, Rolls-Royce, Northrop Grumman, and the U.S. Army.

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THE BONSAI MINDSET

“Organisational transformation is like bonsai work — patient shaping, consistent attention, and the wisdom to know what to prune.”

NOTABLE FACT

All 50 US states — visited.

Every single one. Alaska included.

Outside work, Toby tends bonsai, cooks, travels, gardens, builds things, and collects languages.

NOW AVAILABLE

The AI Leap

The Climb from Pilot to Production · Human-Led · AI-Powered · Built to Last

Type: A business novel that follows one team's full transformation journey — from their first AI experiment to board-level governance. Fifteen chapters. Five frameworks. One field guide wrapped in a story.

This isn’t a theory book. It’s the playbook your team will actually use.

LEAP SUMMIT SHIELD TRAIL RIDGE

Releasing Soon

What leaders are saying

“AI value is created or lost long before a model goes into production. This guidance is exactly what leaders need when the board wants tangible results.”

“Having led analytics and AI transformation for nearly two decades across companies like PayPal, Heineken, Hilton, and now McKesson, I’ve seen that AI value is created or lost long before a model goes into production. In The AI Leap, Toby Rao brings to life the human dynamics, organizational readiness, and execution discipline required to scale AI in healthcare and large enterprises. This grounded, experience-driven guidance is exactly what leaders need when the board wants tangible results, not just more experimentation.”

Shivanku Misra Global Head of AI, McKesson · Board Member, American Society for AI

“Leadership behaviors shape technology outcomes far more than the technology itself. The AI Leap translates this into a story any leader can use.”

“The research is clear: leadership behaviors shape technology outcomes far more than the technology itself. The AI Leap translates this insight into a story that any leader in any sector can feel and use. Based on my two decades of experience leading transformations at scale—from Lean Agile and DevOps modernization to AI adoption—and a doctorate examining leadership’s influence on project results, I affirm this book’s arguments are both well-grounded and practically useful for navigating the complexities of AI.”

Dr. Suzette Johnson Northrop Grumman Fellow & Author

“AI is a people multiplier, not just a tool. It shows leaders how to move from ‘flying blind’ to delivering the impact that actually matters.”

“Toby blends powerful storytelling with pragmatic playbooks to show that AI is a people multiplier, not just a tool. This isn’t a book of theory; it’s a customer-centric field guide focused on solving real problems and shifting mindsets. It shows leaders how to move from ‘flying blind’ to delivering the impact that actually matters.”

Eric O’Brien Founder, Lean Enterprise Organization

Let’s Connect

I write about AI transformation on Medium and LinkedIn. I speak at conferences and community events. If you want to chat about the book, speaking opportunities, or AI transformation, reach out.

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