Who We Are

Kevin is the founder and Principal of Complex Systems Group, LLC.

Attending MIT for undergrad in electrical engineering and computer science, he started working in cybersecurity at Akamai in Boston in 2012, where among other roles he helped run the company’s incident management program. He joined Stripe in 2017, where he helped launch GDPR compliance, then took that to Lyft to help launch CCPA compliance.

After successfully launching CCPA compliance on January 1, 2020 and getting laid off in March, he used that experience to found Complex Systems Group. Since then he’s helped a variety of clients with threat modeling, incident management, and generally to stay ahead of a rapidly-changing security and privacy threat environment.

He is also the host and producer of the Critical Point War Stories podcast, where he interviews (mostly) software engineers about “that time we broke production.”

He blogs in a personal capacity (although sometimes about professionally-relevant topics) at Free Dissociation.

Rachel Silber began consulting with Complex Systems Group in 2025. She brings extensive experience with incident analysis, risk management, and engineering management across the software development lifecycle.

Rachel earned a Computer Science degree from Rutgers University, and worked on software systems in roles from requirements analysis to release engineering, before joining the information security team at Akamai in 2013, where she and Kevin met and collaborated on cybersecurity and incident management projects.

Rachel also writes about engineering management on her blog Voluntary Complexity.

Valerie Thomas is a security researcher and consultant who specializes in social engineering, cyber-physical penetration testing, and critical infrastructure evaluation. After obtaining her bachelor’s degree in Electronic Engineering, Valerie led information security assessments for the Defense of Defense before joining private industry. 

Valerie is the co-author of Building an Information Security Awareness Program: Defending Against Social Engineering and Technical Threats with Bill Gardner.  She has also presented and trained on technical topics at DEF CON, Derbycon, Black Hat, SANS ICS Security, and many other conferences.