Analysts / Jon Oltsik

Jon Oltsik

Distinguished Analyst & ESG Fellow


Distinguished Analyst and ESG Fellow Jon Oltsik founded the cybersecurity practice at Enterprise Strategy Group in 2003 and has spent the subsequent 20 years studying cyber-threats, cyber-risk management, technical defenses, and CISO strategies.

With over 35 years of technology industry experience, he is widely recognized as an expert in all aspects of cybersecurity and is often called upon to help customers understand a CISO’s perspective.

Jon is a founding member of the Cybersecurity Canon, a project dedicated to identifying a list of must-read books for all cybersecurity practitioners, and he was named one of the top 100 cybersecurity influencers by Onalytica. Often quoted in the business and technical press, he is also engaged in cybersecurity issues, legislation, and technology discussions within the US government.

Jon has appeared in The Wall Street Journal, The New Yorker, Forbes, The New York Times, CNBC, Investor’s Business Daily, CSO, Tech Republic, Network World, and Dark Reading, among others. He holds a BA and MBA from the University of Massachusetts, Amherst.

Areas of Expertise

  • Attack Surface Management (ASM)
  • CISO/Enterprise Cybersecurity Programs
  • Cyber Risk Management
  • Deception Technology
  • Managed Security Services
  • Penetration Testing/Red Teaming/Automated Testing (i.e., breach and attack simulation (BAS), continuous automated red teaming (CART), etc.)
  • Process Automation & Orchestration/SOAR
  • Security Analytics
  • Security Asset Management
  • Security Operations
  • Threat Intelligence
  • Vulnerability Management/Exposure Management

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Quoation Mark

Cybersecurity risk has never been greater, while defending against cyber-attacks is more difficult today than it’s ever been. A successful cybersecurity strategy must be a diverse combination of fundamental security hygiene and an openness to new strategic ideas and technology innovation.”

Jon Oltsik
Distinguished Analyst & ESG Fellow
Vertical Pills

Research Report

Security Hygiene and Posture Management Remains Decentralized and Complex

Security hygiene and posture management has become increasingly difficult because of factors like a growing attack surface, the increased use of cloud computing, and the need to support a remote workforce. These factors can create security vulnerabilities that lead directly to cyber-attacks.

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Jon Has Appeared In

Latest Insights from Jon

Research Report | November 30, 2023

The Life and Times of Cybersecurity Professionals Volume VI

Jon Oltsik, Distinguished Analyst & ESG Fellow


Blog | November 9, 2023

Research Points to 5 Ways to Improve Cybersecurity Culture

Jon Oltsik, Distinguished Analyst & ESG Fellow


Blog | November 2, 2023

How to Overcome the Beginner Cybersecurity Career Catch-22

Jon Oltsik, Distinguished Analyst & ESG Fellow