I’m a CISO who’s built many security teams. I want to help you level up your career. Ask me anything.
Source Reddit Cybersecurity
Discussion
This content is an Ask Me Anything (AMA) session hosted by experienced Chief Information Security Officers (CISOs) aimed at helping cybersecurity professionals advance their careers. It focuses on career growth, leadership, and team building within the cybersecurity field. There is no indication of any security threat, vulnerability, or exploit associated with this content.
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The editors at CISO Series present this AMA. This has been a long-term partnership between r/cybersecurity and the CISO Series.
This month, CISO Series has assembled a panel of accomplished security leaders who have built and led many security teams over their careers. They are here to help you level up your own career and to answer your questions about growing in your current role, moving into leadership, hiring and managing teams, and everything in between.
This week's participants are:
- Mathew Biby, (u/RelativeWolf), director of cybersecurity, TixTrack
- Joshua Scott, (u/threatrelic), CISO, Hydrolix
- Janet Heins, (u/JBossOnTheLake), former CISO, ChenMed
- Jim Bowie, (u/IllustriousLadder211), healthcare CISO, Zscaler
- Tomás Maldonado, (u/tomas_mald), CISO, NFL
- Roland Toussaint, (u/AutoExec-exe) head of information security, ChenMed
We addressed career questions like these at Black Hat. This recent video from CISO Series (https://youtu.be/YwG0WmK6Tv4) asks seasoned professionals how they'd approach a career in cyber today. It's a great companion to this AMA, with perspective on how careers in security are changing in the AI era.
Editor's note: This AMA is focused on leveling up for people already working in security, not on getting your first job in the field. Per r/cybersecurity rules, "how do I break in" questions may be removed by the mods, so please keep questions focused on career growth, leadership, and building teams.
This AMA will run all week from 09-27-2026 to 10-02-2026. Our participants will check in over that time to answer your questions.
All AMA participants were chosen by the editors at CISO Series (/r/CISOSeries), a media network for security professionals delivering the most fun you'll have in cybersecurity. Please check out our podcasts and their weekly Friday event, Super Cyber Friday, at cisoseries.com.