Lessons from the Frontlines: Insights from a Cybersecurity Career

by Assaf Keren

Transform your approach to cybersecurity leadership with specific, actionable techniques from a 25+ year veteran of the industry

In Lessons from the Insights from a Cybersecurity Career, a 25+ year veteran of cybersecurity leadership, Assaf Keren, delivers an essential new approach to leading cybersecurity teams. Keren combines engaging, real-life stories drawn from decades spent in the industry – including his current role as Chief Security Officer at Qualtrics and former Chief Information Security Officer in PayPal – with hands-on, specific frameworks for implementing effective solutions in an environment that doesn’t tolerate error.

Lessons from the Frontlines goes beyond generic theory and high-level concepts. It dives deep into practical strategies for working cybersecurity professionals, explaining how to develop the personal characteristics you’ll need to succeed, build leadership competencies your teams will expect from you, address your own mental and physical health needs so you can deal with the challenges you’ll face, and apply all these lessons at scale in organizations of any size.

The author walks you

How to move from permission-seeking approaches to intent-based action that allows you to execute solutions in dynamic environments in real time Strategies for maintaining optimism and a healthy outlook that permits you to endure difficult periods and excel in adversity Techniques for building proactive, forward-thinking, and creative solutions that achieve more than reactive and defensive responses to threats Perfect for practicing and aspiring cybersecurity executives, Lessons from the Frontlines is a must-read strategy guide for all cybersecurity practitioners and professionals interested in rising to – or excelling in – cybersecurity leadership roles.

272 pages, Paperback

Published January 8, 2026

Reviews

[Venkat Ramakrishnan · Rating 5 out of 5]

My first reaction, especially after reading the second section was 'Wow! How close this is to real and not just theoritical!', because I had just gotten out of a meeting with a startup founder who expressed his reservations on how he was going to convince and get buy-in from his co-founders on security investments. I had told him that corporate storytelling with relevant points would help to some extent, but I later realized that that would go only to some extent without a solid framework.

The third section on people and mental well-being honestly feels little like a drag as there is some repetition of same points which could potentially be made crisp to make the book a more enjoyable read.

Overall, I would recommend this book for anyone looking for inputs on security leadership. But hey, I realized that some of the concepts could be used not just in security but also in other key areas of software like performance and observability.

Thanks for this great book, Assaf, and I look forward for more great books from you!

[Matt Hillary · Rating 5 out of 5]

Immediately impactful! Practical, human, and exactly what new and seasoned security leaders need right now. I'm already loving the impacts of practicing what is taught and described in this book. I ordered it for my security leadership team to join me on the journey adopting the principles Assaf outlined here + looking forward to further learning from seeing these in practice. As 4-time CISO, i love so much that it speaks to the HUMAN side of this security leadership role and journey and have had instant resonance with a number of the principles and anecdotes shared. Already happy with the guidance in the mental health / self care sections, too.

[Michelle · Rating 5 out of 5]

A leadership book with deep and specific insights for cybersecurity leaders that every technology leader (not just security) should read. Assaf did a fantastic job of presenting actionable strategies with next steps and prompts for leaders to gain and practice essential skills for success.
The best thing about this book is its substance. It's not one of those leadership books full of fluff and nice anecdotes and 15 stories on the same principle. This book is clear, concise, educational and relatable.

[Lia · Rating 5 out of 5]

Lessons from the Frontlines is the mentorship manual the cybersecurity industry has been waiting for. Assaf Keren expertly bridges the gap between technical defense and human leadership, offering a refreshing framework for moving teams from "permission-seeking" bottlenecks to "intent-based" enablers. Crucially, the book treats mental resilience not as an afterthought but as a strategic necessity, tackling the industry's burnout problem head-on. It is an essential, holistic guide for any practitioner ready to evolve from managing alerts to leading people.

[Josh Bean · Rating 5 out of 5]

Excellent read on leadership. The qualities, skills and frameworks are immediately applicable. I especially appreciate the section on mental health, and the author’s own struggles with it.

[Mike Todasco · Rating 5 out of 5]

Great nonfiction book that reminds you to never forget the human side of things, no matter how technical the work is!