Ahead in the Cloud
Ahead in the Cloud: Best Practices for Navigating the Future of Enterprise IT by Stephen Orban, with forewords by Andy Jassy, Adrian Cockcroft, and Mark Schwartz, is a well‑known cloud‑transformation book focused on how large enterprises modernize through public‑cloud adoption.
What the book is about
Section titled “What the book is about”1. Cloud as a strategic enabler
Section titled “1. Cloud as a strategic enabler”Cloud computing unlocks agility, scalability, and innovation. Orban emphasizes that enterprises must shift from optimizing for efficiency to optimizing for agility and experimentation.
2. Enterprise cloud journeys
Section titled “2. Enterprise cloud journeys”The book includes stories from News Corp, Capital One, GE, and others, showing how large organizations modernize legacy systems, reduce technical debt, and accelerate delivery.
3. Cloud migration strategies (the 6 R’s)
Section titled “3. Cloud migration strategies (the 6 R’s)”Orban outlines the six migration strategies:
- Re‑host
- Re‑platform
- Re‑purchase
- Re‑architect
- Retire
- Retain
These help enterprises prioritize which applications to move first and how.
4. Building cloud‑ready teams
Section titled “4. Building cloud‑ready teams”A major theme: train your existing staff rather than relying solely on external hiring. Upskilling internal teams builds long‑term capability and accelerates adoption.
5. Culture, leadership, and change management
Section titled “5. Culture, leadership, and change management”Orban frames the CIO as a Chief Change Management Officer, responsible for aligning vision, culture, and processes to support cloud transformation.
6. DevOps, CCoEs, and platform thinking
Section titled “6. DevOps, CCoEs, and platform thinking”The book highlights the importance of creating a Cloud Center of Excellence (CCoE) and adopting DevOps practices to standardize cloud usage across the enterprise.
7. Innovation at scale
Section titled “7. Innovation at scale”Cloud enables rapid experimentation, microservices, serverless architectures, and continuous modernization — all essential for competing in a digital economy.
Core takeaway
Section titled “Core takeaway”The book argues that cloud adoption is primarily an organizational and cultural transformation, not a technology migration. Orban draws on his experience as CIO/CTO of Dow Jones and later as Head of Enterprise Strategy at AWS, combining real enterprise case studies with practical frameworks.
Why it matters
Section titled “Why it matters”- Practical, experience‑based guidance from AWS enterprise strategists
- Real‑world case studies from large organizations
- Actionable frameworks for migration, culture change, and modernization