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Digital Trailblazer: Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leadership 1st Edition
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Invaluable stories and lessons that will help you tackle one of the most challenging jobs in technology and business – leading transformation
In Digital Trailblazer: Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leadership, Isaac Sacolick, a technology leadership expert and a former CIO and CTO, delivers a hands-on guide to help technology and business professionals at all stages of their careers acquire the skills necessary to drive transformative change. With an eye-opening collection of stories and more than 50 lessons, Sacolick gives readers a view into what goes on behind-the-scenes in leading digital transformations. From tense IT Ops conference calls to make-or-break executive meetings, Sacolick presents the challenging scenarios faced by product, technology, and data leaders and helps readers learn to lead transformations and become Digital Trailblazers.
In the book you will:
- Step out of your comfort zone and develop the management and leadership skills required to influence executives and win over detractors in driving technology changes
- Learn how to transform experiences, lead data driven organizations, and foster high performance teams
- Discover how to deliver innovation, empower agile self-organization, and evolve standard digital practices that drive culture changes in your organization
A can’t-miss resource for product, technology, and data leaders – from those aspiring to leadership roles through vice presidents, CIOs, CTOs, and CDOs, Digital Trailblazer delivers real-word stories and need-to-know lessons that will accelerate your technology leadership journey.
- ISBN-101119894530
- ISBN-13978-1119894537
- Edition1st
- PublisherWiley
- Publication dateJuly 6, 2022
- LanguageEnglish
- Dimensions6.3 x 1.2 x 9.1 inches
- Print length288 pages
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Editorial Reviews
From the Inside Flap
An essential guide to help you tackle the most challenging job in business and technology – leading transformation.
We’re living in a time of nonstop transformation. Business, technology, and data professionals who develop the skills necessary to lead transformation will accelerate their careers, advance their organizations, and future-proof themselves against inevitable change.
In Digital Trailblazer: Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leadership, tech leadership expert and veteran chief information and technology officer Isaac Sacolick delivers a hands-on guide on how to expand your skills and grow confidence in leading through culture, process, and technology changes.
Leading transformative change requires wide-ranging skills, from defining and sharing a vision to winning hearts and minds. With an eye-opening collection of stories, Sacolick gives readers a view into what goes on behind the scenes in leading digital transformations and shares over 50 practical lessons and strategies readers can immediately apply to their work.
Digital Trailblazer offers a rare insider’s view of the challenging scenarios faced by product, technology, and data leaders, from tense IT Ops conference calls to make-or-break executive meetings, helping readers learn from these real-world examples.
An indispensable resource for aspiring product, tech, and data leaders―as well as experienced professionals in VP, CIO, CTO, and CDO roles―Digital Trailblazer will help you advance your leadership skills and grow your organization into a nimble, agile, and digitally capable competitor.
From the Back Cover
PRAISE FOR DIGITAL TRAILBLAZER
“Isaac gives digital leaders a programmatic and comprehensive approach to tackling the everchanging challenges in digital transformation. Digital Trailblaze is the must-go-to playbook for not only leadership advice, but also real-world stories on how to handle the toughest challenges in culture, process, and technology.”
―R “Ray” Wang, Founder and CEO, Constellation Research, and two-time bestselling author, Disrupting Digital Business and Everybody Wants to Rule the World
“You’d be hard-pressed to find another author with a closer knowledge of both IT management and the underlying technology that powers enterprises. Isaac Sacolick has been there and done that as a CIO, so his advice is hard-bought―and thanks to his sharp writing skills, clear as a bell. Anyone involved in a transformational IT initiative would do well to read this book.”
―Eric Knorr, Editor-in-Chief, IDG
“Finally, a guide to career growth from techy to top dog. Isaac’s story-led approach breaks down the imposter syndrome barrier new leaders face and imparts practical knowledge in a consumable way, saving the reader from experiencing the pain of making the same mistakes.”
―Helen Wetherley Knight, Co-Founder, TechForSocialGood.ca
“Isaac Sacolick holds a unique vantage point in the CIO world. From individual contributor to board partner, he has seen and done it all. His latest book offers a roadmap to the opportunities and challenges of being a modern Chief Information Officer. It’s a world where technology is the crucial enabler of transformation, and the CIO is a business leader first. Isaac’s journey is personal, important, and offers valuable lessons to the rest of us. If you are a CIO or aspiring CIO, then read this book.”
―Michael Krigsman, Publisher, CXOTalk
“Digital Trailblazer should be required reading for rising technology and business leaders. The candid stories and pragmatic lessons will help you take your career to the next level and prepare you for the many challenges you’re bound to face in the future.”
―Dan Roberts, CEO, Ouellette & Associates Consulting, and Host, CIO Whisperers Podcast
“I have had the pleasure of working with Isaac for several years in his role as a leader of numerous executive-level discussions for CIOs at the programs I run. His sessions are always the standout, must-join piece of content at our events. His first book, Driving Digital, was a revelation, and I regularly advise my CIO clientele to treat it as a bible for digital transformation. This next installment might just be even better. Don’t miss it!”
―Ross Abbott, CEO and Founder, SINC USA
About the Author
ISAAC SACOLICK is Founder and President of StarCIO, a technology learning company that guides leaders on digital transformation. A lifelong technologist, Isaac has served in startup CTO and transformational CIO roles. He founded StarCIO with the belief that agile ways of working and data-driven practices can empower diverse teams to drive transformation. He is a writer, keynote speaker, and author of the bestseller, Driving Digital: The Leader’s Guide to Business Transformation Through Technology. He is a frequent contributor to InfoWorld and CIO.com where he writes about digital transformation, agile management, and other technology and leadership topics.
Product details
- Publisher : Wiley; 1st edition (July 6, 2022)
- Language : English
- Hardcover : 288 pages
- ISBN-10 : 1119894530
- ISBN-13 : 978-1119894537
- Item Weight : 1.05 pounds
- Dimensions : 6.3 x 1.2 x 9.1 inches
- Best Sellers Rank: #484,529 in Books (See Top 100 in Books)
- #322 in Information Management (Books)
- #386 in Computers & Technology Industry
- #5,612 in Leadership & Motivation
- Customer Reviews:
About the author

Isaac Sacolick is a successful CIO who has led digital transformation, innovation, agile, and data science programs in multiple organizations. He has transformed underperforming businesses by delivering new digital products, investing in strategic technologies, enabling agile practices, outsourcing commodity services and establishing performance metrics. Isaac has been recognized as a top 100 social CIO, blogger, and industry speaker.
Customer reviews
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Learn more how customers reviews work on AmazonReviewed in the United States on July 1, 2022
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Top reviews
Top reviews from the United States
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There’s prescriptive advice for all kinds of leaders, not just those in CIO/CTO roles, but it’s not a magical “do these X things in Y order, and your digital transformation efforts will always work” book. It explores problems and pitfalls, challenges and opportunities, successes and less-than-successes, but it always keeps people, process, and culture front and center. It also makes the point that “digital transformation” was going on long before it became an industry buzzword.
I’ve been more of a digital foot-soldier than a trailblazer, but peeks behind the C-suite curtain and seeing the outcomes of those kinds of deliberations make all of Isaac’s stories and advice ring true. As such, it’s also a great book for folks outside the C-suite to gain insight into the big WHYS of the orders we all-too-often receive without quite enough context.
Highly recommended!
Isaac uses personal stories from his career to illustrate the many challenges you'll encounter when taking on a transformation project. There were times I couldn't believe I was getting such insider detail about what happens behind closed doors on technology projects. I felt like a fly-on-the-wall of meetings and scenarios that I haven't yet experienced in my career. I appreciated Isaac's vulnerability and candor – it's not something I've seen a lot of in the other technology business books that I've read and it stood out to me. His storytelling approach also made this a fun, quick read.
Best of all, whether you're in a technical role or not, Isaac lays out clear guidance on how to approach all aspects of leading a transformation project – from getting buy-in for new ideas to influencing people and effectively dealing with naysayers. Throughout the book, there are call-outs that elaborate on the lessons he wants you to take away. And each chapter ends with a list of specific lessons that would take years and lots of mentoring to learn on your own. I highly recommend this book.
Reviewed in the United States 🇺🇸 on July 1, 2022
Isaac uses personal stories from his career to illustrate the many challenges you'll encounter when taking on a transformation project. There were times I couldn't believe I was getting such insider detail about what happens behind closed doors on technology projects. I felt like a fly-on-the-wall of meetings and scenarios that I haven't yet experienced in my career. I appreciated Isaac's vulnerability and candor – it's not something I've seen a lot of in the other technology business books that I've read and it stood out to me. His storytelling approach also made this a fun, quick read.
Best of all, whether you're in a technical role or not, Isaac lays out clear guidance on how to approach all aspects of leading a transformation project – from getting buy-in for new ideas to influencing people and effectively dealing with naysayers. Throughout the book, there are call-outs that elaborate on the lessons he wants you to take away. And each chapter ends with a list of specific lessons that would take years and lots of mentoring to learn on your own. I highly recommend this book.
The author has done a commendable job at drawing upon his rich first hand digital transformation experience and distilling the learnings into this book.
The key aspects of the book that I liked -
1. The delivery of lessons via stories make the content relatable and easy to understand. These author lets you step into his shoes to appreciate what is going in the moment and how to best respond.
2. The direct and "frank" language, rich with fitting analogies, leave no room for ambiguity on the point being made. For example, "Fixing defects and operational issues are the must eat vegetables on the side of the product owners' perfectly well-seasoned steak"
3. The summary at the end of each chapter and in the appendix, not only help reinforce the key points, but also make it easy for the reader to go back for future reference.
Highly recommended read!
Reviewed in the United States 🇺🇸 on July 27, 2022
The author has done a commendable job at drawing upon his rich first hand digital transformation experience and distilling the learnings into this book.
The key aspects of the book that I liked -
1. The delivery of lessons via stories make the content relatable and easy to understand. These author lets you step into his shoes to appreciate what is going in the moment and how to best respond.
2. The direct and "frank" language, rich with fitting analogies, leave no room for ambiguity on the point being made. For example, "Fixing defects and operational issues are the must eat vegetables on the side of the product owners' perfectly well-seasoned steak"
3. The summary at the end of each chapter and in the appendix, not only help reinforce the key points, but also make it easy for the reader to go back for future reference.
Highly recommended read!
He uses call-out boxes to make a point, clarify, and highlight important information. At the end of each chapter is an excellent summary of the lessons learned from the story and how to translate those into action. (I also love how he summarized all of these points at the end of the book in a very easy-to-use reference).
I have already started recommending this book to all my CIO and IT leader clients!
Top reviews from other countries
Written as a novel, Isaac has written a semi-autobiographical book, using his extensive IT experience in start-ups as well as major corporations.
Each chapter is a business scenario, for example, the critical application that is being developed and is behind schedule, the merger with another company, the lack of Agile and DevOps skills on a project. You are there in the Boardroom with Isaac, what are you going to do?
Isaac, then takes you through what he did with outcomes both good and bad.







