Podcast
The Cyber Talent Series
Hosted by SkillBit (Formerly MetaCTF) · EN
Cybersecurity talent management is nuanced. Traditional best practices around hiring, onboarding and professional development may not translate effectively into the security domain. The best leaders in cybersecurity are particularly adept at assessing, measuring, and managing security professionals accounting for the unique nature of security teams.
Join Thomas Rogers, Co-Founder of SkillBit (Formerly MetaCTF), and co-host Phoebe DeVito, as they uncover practical tips and best practices from InfoSec leaders on how they excel at building and managing world class teams.
10episodes
Episodes
Newest firstAll episodes
Cyber Talent Series 19: Building by Doing and AI-Powered Security with Grant Smith
May 1200:30:19Tap to summarizeCybersecurity talent management is nuanced. Traditional best practices around hiring, onboarding and professional development may not translate effectively into the security domain. The best people in cybersecurity are particularly adept at assessing, measuring, and managing security professionals.Join Thomas Rogers, Co-Founder of Skillbit, as he connects with Grant Smith, Red Team Lead at Ally and CEO & Co-Founder of Surface Security, to discuss breaking into offensive security. Grant shares how his experience leading red teams shaped his approach to mentoring talent, evaluating candidates in the age of AI-assisted interviews, and balancing technical expertise with strong people skills. He also discusses the launch of Surface Security, the evolving browser security landscape, and how AI is reshaping both phishing attacks and modern security defenses.
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Cyber Talent Series 18: On-the-Job Training, Mission-driven Leadership, and AI with Alex Collison
Apr 1400:29:43Tap to summarizeCybersecurity talent management is nuanced. Traditional best practices around hiring, onboarding and professional development may not translate effectively into the security domain. The best people in cybersecurity are particularly adept at assessing, measuring, and managing security professionals.Join Thomas Rogers, Co-Founder of SkillBit, and co-host Phoebe DeVito as they connect with Alex Collison, Director of Information Security, Surface Area Management at Cargill, to discuss leading across vulnerability management, threat intelligence, and offensive security. Alex shares how she empowers her teams with autonomy and clear outcomes, and why leaning into discomfort is critical for growth. She also offers her perspective on upskilling through hands-on experience and navigating the security landscape influenced by the evolution of AI.
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Cyber Talent Series 17: Creating Psychological Safety and Building a Team Culture Around Curiosity
Mar 3100:37:32Tap to summarizeCybersecurity talent management is nuanced. Traditional best practices around hiring, onboarding and professional development may not translate effectively into the security domain. The best people in cybersecurity are particularly adept at assessing, measuring, and managing security professionals.Join Thomas Rogers, Co-Founder of SkillBit (formerly MetaCTF), and co-host Phoebe DeVito as they connect with Jose Ramos, Head of Offensive Security at Uber, to discuss transitioning from hands-on technical roles into leadership. Jose shares his approach for mentoring talent, understanding burnouts, and knowing when to hire. He also shares his perspective on how to balance build vs. buy decisions in a rapidly evolving landscape shaped by AI and new security tools. Throughout the episode, Jose reflects on the importance of resilience, continuous learning, and embracing failure as a foundation for long-term growth.
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Cyber Talent Series 16: Introducing SkillBit
Mar 1700:19:22Tap to summarizeJoin co-host Phoebe DeVito as she turns the microphone on fellow co-host Thomas Rogers to discuss MetaCTF's transition to SkillBit. Thomas shares the origins of MetaCTF, the philosophy behind hands-on CTF-based learning, and how that foundation evolved into a broader platform for cybersecurity skill development that's better captured with the name, SkillBit. They also explore the vision behind SkillBit’s bite-sized training model, the role of AI in guiding skill development, and how organizations can better measure and grow cybersecurity talent.
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Cyber Talent Series 15: Building Curious, High-Performance Cyber Teams
Mar 300:39:25Tap to summarizeCybersecurity talent management is nuanced. Traditional best practices around hiring, onboarding and professional development may not translate effectively into the security domain. The best people in cybersecurity are particularly adept at assessing, measuring, and managing security professionals.Join Thomas Rogers, Co-Founder of SkillBit (formerly MetaCTF), and co-host Phoebe DeVito as they speak with Joe McCallister, Senior Manager of Cybersecurity at The Trade Desk, about building and leading modern cybersecurity teams. Joe shares his unconventional path from retail and sales into cybersecurity leadership and how those early experiences shaped his approach to hiring, mentoring, and developing talent. The conversation explores why curiosity and community are critical traits in cybersecurity and how managers can evaluate these traits in candidates when building teams. Joe emphasizes the importance of psychological safety to allow for open lines of communication to avoid burnout and encourage collaborative conversations about career growth. Joe reflects on transitioning from an individual contributor to a leader and the importance of "letting go" and trusting your team to take on new opportunities.
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Cyber Talent Series 14: Exploring the Cyber Skills Gap and Taking Action
Feb 1700:37:28Tap to summarizeCybersecurity talent management is nuanced. Traditional best practices around hiring, onboarding and professional development may not translate effectively into the security domain. The best people in cybersecurity are particularly adept at assessing, measuring, and managing security professionals.Join Thomas Rogers, Co-Founder of SkillBit (formerly MetaCTF), and co-host Phoebe DeVito as they connect with Kevin Woods, Director of Learning and Development at GuidePoint Security. In this episode, Kevin shares his perspective on bridging the cyber skills gap by building scalable training programs and creating structured yet flexible learning pathways. Kevin discusses the importance of being disciplined and proactive to building a cybersecurity career. The episode also explores how organizations can invest in entry-level talent and design learning programs that drive retention and long-term success in the industry.
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Cyber Talent Series 13: Staying Technical, AI in Security, and Deciding When to Build vs. Buy
Feb 300:30:46Tap to summarizeCybersecurity talent management is nuanced. Traditional best practices around hiring, onboarding and professional development may not translate effectively into the security domain. The best people in cybersecurity are particularly adept at assessing, measuring, and managing security professionals.Join Thomas Rogers, Co-Founder of MetaCTF, and co-host Phoebe DeVito as they connect with Antoinette Stevens, Principal Security Engineer at Ramp, to discuss growing detection and response teams, transitioning into people leadership while staying hands-on, and hiring for humility and curiosity. Antoinette also shares how she approaches build vs. buy decisions, and why mastering the fundamentals matters before layering in AI-driven capabilities.
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Cyber Talent Series 12: Interview Rubrics, AI in hiring, and Cyber Talent Series 12: Interview Rubrics, AI in hiring, and Moving into Leadership
Jan 2000:25:29Tap to summarizeCybersecurity talent management is nuanced. Traditional best practices around hiring, onboarding and professional development may not translate effectively into the security domain. The best people in cybersecurity are particularly adept at assessing, measuring, and managing security professionals.Join Thomas Rogers, Co-Founder of MetaCTF, and co-host Phoebe DeVito as they chat with cybersecurity industry veteran, Rob "mubix" Fuller. Rob shares the importance of establishing interview rubrics and tips on transitioning into a leadership role as someone who also loves being "hands-on-keyboard". Their conversation also explores mentorship, community involvement, and why curiosity and humility remain essential at every stage of a cyber career.
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Cyber Talent Series 11: Hack, Build, Repeat
Jan 600:27:43Tap to summarizeCybersecurity talent management is nuanced. Traditional best practices around hiring, onboarding and professional development may not translate effectively into the security domain. The best people in cybersecurity are particularly adept at assessing, measuring, and managing security professionals.Join Thomas Rogers, Co-Founder of MetaCTF, and co-host Phoebe DeVito as they connect with Mike Takahashi, Director of Security Engineering at BetterHelp and AI Red Teamer. On this episode, they discuss hiring for real-world skills, building teams grounded in curiosity, and developing talent through autonomy and trust. He shares insights on AI security and the risks and opportunities of agent-based models. Although credentials are important, Mike explains why hacking, building, and experimenting matter even more in the age of AI.
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Cyber Talent Series 10: Building a Swiss Army Knife Cyber Team in the Age of AI
Dec 900:32:01Tap to summarizeCybersecurity talent management is nuanced. Traditional best practices around hiring, onboarding and professional development may not translate effectively into the security domain. The best people in cybersecurity are particularly adept at assessing, measuring, and managing security professionals.Join Thomas Rogers, Co-Founder of MetaCTF, and Chitra Dharmarajan, VP of Security and Privacy Engineering at Okta, as they discuss building balanced, collaborative, and adaptable security teams. Chitra shares her journey going from developer to security executive, the importance of soft skills in technical roles, and why diverse skill sets are key to scaling security programs. She also explores how AI is reshaping the workforce, from accelerating upskilling to redefining what it means to be “junior” in cybersecurity.
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