Guest Introduction

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.

Here's a Glimpse of What You'll Learn

• Why diverse industry experience strengthens security leadership

• How human centered leadership improves security outcomes

• Where AI helps security teams and where it creates new risk

• Why doing the basics well still matters more than new tools

• How AI can reduce user friction while improving protection

• What reasonable security looks like in an era of nation state threats

• Why investing in teams delivers better long term defense

In This Episode

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.

Sponsor for this episode...

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