Jess Vachon is a three time CISO, the founder of Vigilant Violet LLC, and the host of the Voices of the Vigilant Podcast. With a career spanning manufacturing, defense, robotics, software, healthcare, and global financial services, Jess brings a uniquely broad perspective to cybersecurity leadership. Her journey reflects a deep commitment to building security programs that balance technical rigor with human centered leadership. Across every role, Jess has focused on developing resilient teams, pragmatic security strategies, and leaders who understand both risk and responsibility.
Jess Vachon explains how her path to becoming a CISO was shaped by working across multiple industries and building security programs from the ground up. She shares how creating a full security program at a defense manufacturer helped confirm that security leadership was where she could make the greatest impact. That experience also reinforced her belief that hard problems with visible outcomes are the most rewarding.
The conversation explores the role of AI in modern security, with Jess emphasizing that productivity gains should not come at the expense of people. She challenges the idea that AI should simply replace staff and instead argues for using it to increase effectiveness, retain institutional knowledge, and reduce unnecessary friction for employees. Her perspective reframes AI as a tool that supports humans rather than one that sidelines them.
Jess and Matthew also discuss why security tools must be purpose built rather than bolted on with buzzwords. Using real world examples, she explains how machine learning can quietly protect users by understanding behavior and stopping threats before employees even see them. This approach reduces blame, improves trust, and shifts security closer to being invisible but effective.
The episode closes with a powerful leadership discussion shaped by Jess’s Marine Corps experience. She shares how military service taught her to lead under pressure, maintain perspective during crises, and focus on outcomes without losing sight of people. That mindset continues to inform how she views risk, response, and the responsibility of modern security leaders.
Resources mentioned in this episode
Matthew Connor on LinkedIn
This episode is brought to you by CyberLynx.com
CyberL-Y-N-X.com.
CyberLynx is a complete technology solution provider to ensure your business has the most reliable and professional IT service.
The bottom line is we help protect you from cyber attacks, malware attacks, and the dreaded Dark Web.
Our professional support includes managed IT services, IT help desk services, cybersecurity services, data backup and recovery, and VoIP services. Our reputable and experienced team, quick response time, and hassle-free process ensures that clients are 100% satisfied.
To learn more, visit cyberlynx.com, email us at help@cyberlynx.com, or give us a call at 202-996-6600.
Balancing AI, Privacy, and Risk at a Public University with Malcolm Blow