The Cyber Security Recruiter Podcast

Thomas Richard
  • 4.2 (6)
  • Technology
  • Updated Weekly

The mission is simple: To enhance your career growth within the Cybersecurity community & bring interesting and knowledgable guests onto the Podcast so that you can benefit from their experience.

  1. 1d ago

    Thomas Richard talks to Jeff Bailey, Director, IT and Information Security, Apptegy

    Protecting Student Data, Leading Security Teams, and Keeping Up With AI: Jeff Bailey on Security Leadership Thomas chats with Jeff Bailey on the Cybersecurity Recruiter podcast about his career path from GameStop into security roles at Simmons Bank and now as Director of Security and IT at Apptegy, a K–12 communications platform focused on protecting sensitive student data across all 50 states’ regulations. They discuss how rapidly evolving AI models (including Fable and Opus) are changing security work, vendor risk/GRC reviews as SaaS apps add AI features, and how teams can build small internal tools instead of buying expensive products. Jeff shares leadership lessons on perception and trust: making security approachable (including his bright shirts), encouraging reporting, and empowering experts to challenge him, while managing workload to prevent burnout by aiming for 80% capacity. They also cover AI’s impact on learning, CTF competitions, and parenting in an AI-saturated world. Book recommendation: “Time Management for Mortals” by Oliver Burkeman; Jeff also recommends Adam Grant’s work. 00:00 Welcome and Catch Up 00:52 Jeff Bailey Career Intro 01:36 ADHD and Security Culture 03:27 Director Role at Apptegy 04:42 Fable vs Opus AI Talk 07:57 Kids Growing Up With AI 09:36 Token Costs and IPO Pricing 11:06 Purpose Protecting Student Data 13:54 Leadership and Approachability 18:32 Empowering Experts on Your Team 20:03 Avoiding Burnout at 80% 21:22 AI Like the Cloud Shift 22:28 New AI Security Reviews 23:06 Vendor Acronyms and Confusion 23:56 Adapt or Get Left Behind 25:50 AI Slop in Customer Touch 28:45 Using AI for Real Gains 31:30 CTFs and AI Cheating 33:07 Learning Still Needs Struggle 35:56 Book Picks and Wrap Up For Executive, GTM, Cybersecurity searches, contact Tom: https://www.linkedin.com/in/thomaspropen/

    Thomas Richard talks to Jeff Bailey, Director, IT and Information Security, Apptegy

  2. Jul 31

    Thomas Richard chats with Michael Greenlaw, Founder & CEO, FedRock

    Michael Greenlaw on AI, DevSecOps, and FedRAMP Automation: Speed, Risks, and the Need for Fundamentals Tom and Michael discuss Microsoft’s strategy and licensing shifts pulling organizations toward Windows and Azure, and the frustration of incompatible cloud service naming across AWS/Azure/GCP. Michael describes using Claude to learn and build with LLMs rapidly, calling it “fast Google,” but warns about hallucinations, compounded errors in chained tasks, human limits in reviewing massive AI-generated code, poor handling of branching strategies, and the need for humans to own architecture and fundamentals. They debate layoffs attributed to AI versus post-COVID overhiring and shareholder optics, and note AI’s growing impact on vulnerability discovery and exploitation. Book recommendations: “How to Win Friends and Influence People” (Dale Carnegie), “The Trusted Advisor,” and “Thinking in Bets.” 00:00 Welcome and Intro 00:39 Career Path Update 01:25 Why Windows Again 05:41 Cloud Naming Frustrations 07:27 Keeping Up With Titles 09:12 AI Learning Acceleration 11:36 Curiosity in Hiring 15:39 Market Whiplash Era 19:11 FedRock and AI Experiments 22:19 Automating Workflows With RPA 24:31 AI Saving Lives Story 25:44 AI Pitfalls and Guardrails 31:09 Markets Overhyped AI 33:02 AI Errors And Whiplash 33:50 Why Juniors Still Matter 35:34 Overhiring Blamed On AI 38:11 Metrics Gaming And Talent 40:32 Shareholders And Productivity 42:28 AI Addiction And Frustration 47:08 Learning Boosts And Security Risks 51:58 Using AI With Responsibility 55:16 Scale Problems In Big Orgs 57:06 Books That Changed Everything 01:02:19 Closing Thanks And Wrap Up Nexo - Executive, GTM & Cybersecurity Recruitment https://www.linkedin.com/in/thomaspropen/

    Thomas Richard chats with Michael Greenlaw, Founder & CEO, FedRock

  3. Jul 28

    Thomas Richard & Lindsay Kaye, VP of Threat Intelligence, HUMAN Security & Book Author

    00:00 Welcome and introductions 00:39 Lindsay career snapshot 01:41 Threat intel at Human 02:37 New book launch 03:33 Malware needs context 04:42 Spotting real people online 08:25 AI as attack amplifier 09:45 Phishing at scale 11:50 Democratized hacking risks 15:18 Path to VP leadership 20:00 AI proof risk communication 21:53 Time boxing MIT MBA grind 23:13 Writing a book discipline 23:49 Small wins and purpose 25:15 Book writing deepens mastery 26:39 Communication skills through practice 29:15 Behind the scenes struggles 32:02 Mentors versus sponsors 34:41 Security community collaboration 35:48 Whats next and book teaser 37:46 Boat go faster mantra 39:49 Final thanks and wrap up

    Thomas Richard & Lindsay Kaye, VP of Threat Intelligence, HUMAN Security & Book Author

  4. Jul 24

    Thomas Richard talks to Spencer Grant, Lead R&D Recruiter at 7AI

    Recruiting in cybersecurity & AI: Relationships, what great candidates do, and fixing broken hiring processes Thomas hosts the Cybersecurity Recruiter podcast with Spencer Grant, lead recruiter at 7AI, discussing recruiting realities, relationship-driven hiring, and how top candidates stand out. Spencer describes his career path largely shaped by following a strong manager and emphasizes providing a “three-star Michelin” candidate experience. They outline traits of great candidates: depth of technical understanding (the “whys”), outcome-focused thinking tied to business ROI and honesty paired with curiosity. Spencer critiques broken application processes and advises proactive outreach after applying, strong interview preparation - company research, coding/system design readiness - and asking substantive questions. They discuss AI’s impact on jobs, valuing human touch over automated screening, and Spencer’s Meta layoff and contracting path back to full-time. Book recommendation: “The Mental Game: Winning the War Within Your Mind.” 00:00 Welcome and wins 00:47 Recruiter reality check 02:21 Spencer career intro 04:06 Relationships over tools 08:29 What makes candidates great 14:06 Curiosity and learning fast 19:03 Hiring process mistakes 23:37 Manual recruiting over AI 26:37 High touch candidate experience 27:43 AI expands security jobs 29:35 Layoffs and market cycles 31:52 Rebounding after Meta layoff 34:16 Contracting as a strategy 35:01 Office osmosis learning 39:04 Culture and knowledge sharing 42:04 Mindset book recommendation 46:54 Final thanks and wrap

    Thomas Richard talks to Spencer Grant, Lead R&D Recruiter at 7AI

  5. Jul 22

    Thomas Richard chats to Chad Fullerton, VP of Information Security, ECI

    Chad Fullerton on AI, Claude Code, and Staying Valuable in Cybersecurity Tom chats with Chad Fullerton, a former US Navy member and current VP of Information Security at ECI, about his career path, family life, and how AI is reshaping work. Chad emphasizes fundamentals like caring, continuous learning, and maintaining a positive mindset, noting he consumes about 120 audiobooks a year. He describes practical AI use cases such as using Claude to merge multiple pen test reports quickly, warns that deliverables and contracts will be reviewed by AI, and discusses token costs. He argues AI shifts value toward industry expertise, client-facing advisory skills, and automating small time savings at scale, not just coding, and advises professionals to adapt rather than fear disruption. Book recommendations include Uniquely Human (Barry Prizant), Good to Great, and CISSP 11th Hour, plus Brandon Sanderson’s fantasy books. 00:00 Welcome and Setup 00:45 Meet Chad Fullerton 02:01 Day in the Life 03:18 AI Revolution Pace 04:37 Fundamentals and Growth 05:41 Learning Habits That Compound 09:39 AI in Security Workflows 11:55 Claude Code and Automation 18:43 Adapting to Disruption 20:42 Positivity and Hiring Signals 26:10 Layoffs and Reputation 27:41 LinkedIn Is Not Therapy 31:43 Clicks at Scale 34:01 Stop Being Cost Center 36:37 Advisors Beat Hoodies 40:14 Work Backwards Roadmap 42:21 Daily Learning Mindset 43:29 Books That Shaped Chad 47:29 Sales Outreach Done Right 49:08 Social Media Reality Check 49:56 Wrap Up and Next Time Nexo - Executive, GTM & Cybersecurity Recruitment https://www.linkedin.com/in/thomaspropen/

    Thomas Richard chats to Chad Fullerton, VP of Information Security, ECI

  6. Jul 8

    Thomas Richard talks to Dixon Wright, Managing Director, Riveron

    Dixon Wright on career growth, leadership paths, and using AI without losing expertise Thomas chats with Dixon Wright about his career progression and what drives promotions, emphasizing hard work plus being in the right place at the right time. Dixon discusses playing the long game, building subject-matter expertise before leading, and the importance of choosing work you enjoy rather than chasing compensation. He highlights the value of early consulting for transferable skills, professionalism, and in-person learning, and warns remote work and AI can weaken development and enable shortcuts. They explore AI’s ROI, token costs, and how metric-driven cultures can reward low-value ‘activity’, arguing expertise is still essential to evaluate ideas and business impact. Book/podcast recommendations include How I Built This, Radical Candor, The Advantage, Deep Work, Digital Minimalism, Slow Productivity, and Unreasonable Hospitality. 00:00 Welcome and Guest Intro 01:30 Life as a Remote Dad 02:57 Career Growth and Promotions 05:31 Play the Long Game 08:32 Choose Passion Over Pay 12:49 Superstars vs Rock Stars 16:14 Why Consulting Builds Skills 20:09 AI Remote Work and Learning 22:57 AI ROI and Hidden Costs 35:03 Books Habits and Wrap Up

    Thomas Richard talks to Dixon Wright, Managing Director, Riveron

  7. Jul 7

    Thomas Richard talks to Mike Wilkes, Enterprise CISO at Aikido Security

    Mythos, Autonomous Pen Testing, and the Future of Self-Securing Software, with Mike Wilkes, Enterprise CISO at Aikido Security. On the Cyber Security Recruiter podcast, Mike Wilkes discusses a busy week of CISO events at Google (Mythos/Glasswing gathering), the Harvard Club, and Meta’s OSAC cybersecurity committee, plus an NYSE TV interview about Aikido Security’s Series B and growth. He explains Mythos Preview’s implications, including rapid vulnerability discovery (citing Firefox fixing 271 issues vs 20–30 historically), Anthropic’s restrictions, and the need for prioritization (EPSS) rather than chasing raw CVE volume. Mike describes autonomous pen testing where a $7,000, two-week API test was replicated for $4 in 80 minutes, arguing the “harness” and orchestration matter most. He emphasizes soft skills, listening, and translating security into business impact for boards, warns about privacy erosion, token-cost waste, supply-chain/model risks, and advocates small local models for privacy and resilience.

    Thomas Richard talks to Mike Wilkes, Enterprise CISO at Aikido Security

  8. Jul 1

    The Cybersecurity Recruiter talks to Manal Iskander, Founder, PCtronics Managed IT, Security and Automation

    AI-Native Cybersecurity, MSP Automation, and What Education Must Change Next - with Manal Iskander On the Cybersecurity Recruiter podcast, the host speaks with Manal Iskander, founder of PCtronics , co-owner of Green Shack Marketplace, and Marketing Lead at Fugazi about how AI and cybersecurity are now inseparable and how she’s using an AI-native, agentic software stack (including SuperOps, NinjaOne, SentinelOne, Huntress, and SharePoint-based automation) to speed onboarding, triage tickets, and generate monthly security and operations reporting that drives recurring revenue plus project work. She describes using a human-centered “double diamond” approach (discover, define, design, deliver) with governance and accountability to decide what to automate vs. keep human-in-the-loop, giving examples like overriding blocked logins for a traveling CEO. She discusses private equity buying MSPs based on MRR, her goal to build toward a much larger exit, and her July 30 keynote in Sacramento for California higher-education CTOs on standardized AI adoption, governance, curriculum shifts toward critical thinking, and risks like Anthropic’s “Mythos” zero-day tool. Book recommendations mentioned: “Abundance,” “The Human Fork Encoded,” and “The 80-Year Theory.” 00:00 Welcome and Introductions 00:28 Keynote and AI Security 01:51 Manel Background Story 03:25 Restaurants and Balance 04:47 Building an AI Native MSP 07:25 PBS Show Origin Story 09:47 Tech as Human Extension 13:54 Human in the Loop Security 15:19 Double Diamond Workflow 19:58 Automated Reporting Engine 23:20 Private Equity and Exit Plans 24:41 Leaving Reporting Teams 25:30 AI Tools For Operations 25:52 AI Boom For Business 26:57 Education Adapts To AI 30:18 Governance For Universities 31:30 Mythos Zero Day Fears 32:48 AI Geopolitics And Money 37:06 Human Fork And Cycles 40:22 Future Work And UBI 42:23 Keeping Up With Pace 43:42 July Keynote Preview 46:46 Adoption Divide And Wrap

    The Cybersecurity Recruiter talks to Manal Iskander, Founder, PCtronics Managed IT, Security and Automation
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4.2
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About

The mission is simple: To enhance your career growth within the Cybersecurity community & bring interesting and knowledgable guests onto the Podcast so that you can benefit from their experience.

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