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

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.

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

Marketing, personal branding, and networking for cybersecurity careers with Gary Piper

Tom introduces a delayed Cybersecurity Recruiter Podcast episode with Gary Piper, Marketing Director at Black Talon Security, and outlines Gary's career from graphic design and creative leadership into cybersecurity marketing.

Gary discusses the growing need for clear cybersecurity marketing, emphasising the importance of understanding a company's story, purpose and differentiators, while learning technologies well enough to communicate them effectively.

He also shares lessons from a layoff in 2018, including the importance of keeping your CV and portfolio updated, staying aware of market opportunities, and continually building relationships with recruiters and your network.

For personal branding, Gary recommends understanding what motivates you, highlighting what makes you different, and being willing to experiment with new platforms and approaches. He also discusses the importance of emotional intelligence, mentorship, communication skills and face-to-face networking.

Reading/learning recommendations from Gary:

• Crucial Conversations: Tools for Talking When Stakes Are High by Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler which is a program focused on handling difficult conversations, conflict resolution, and communication.
• Situational Leadership by Ken Blanchard, a leadership course about adapting leadership styles to different people and situations.
• Co-Active coaching training developed by Henry Kimsey-House, Karen Kimsey-House, Phillip Sandahl, and Laura Whitworth focused on active listening and professional coaching skills

00:00 Late release intro

00:49 Meet Gary Piper

02:14 From design to cyber marketing

03:36 Explaining cyber to buyers

06:03 Breaking into security

07:12 Networking that pays off

09:20 Staying job market ready

12:42 Personal branding basics

17:39 Brand building takes time

25:10 Healthy conflict at work

26:54 Communication over tech

27:42 Scaling team leadership

29:25 Should you lead?

31:00 Managing personalities

33:10 Remote work reality

36:37 Active listening coaching

38:06 Finding great mentors

40:12 Industry community vibes

41:50 Events and cyber risk

45:19 Recruiting meets marketing

47:01 Security marketing pitfalls

48:19 Final wrap up

Craig Adams on Building Security Products: Why Me/Why Now, AI-Driven Remediation, and Extreme Ownership

Tom chats with Craig Adams, Chief Product Officer at Rapid7 and Board Member at Peak Metrics.

Adams describes himself as a builder, focused on driving revenue growth through technology by avoiding innovation that isn’t leveraged and by anchoring product strategy in “why me, why now,” plus strong execution.

They discuss how AI has improved risk identification and verdicting (e.g., faster pen-test-like assessments) but has worsened alert volume, shifting cybersecurity’s center of gravity to remediation and response, including granular, agentic actions beyond traditional SOAR rules. Craig discusses how rapid industry change shortens roadmap planning to roughly nine-month increments, and he shares hiring priorities: attitude, work ethic (intensity), and intelligence defined as curiosity. They cover mission-driven teams, repetition in culture, EQ over IQ in leadership, and Craig recommends the book “Extreme Ownership,” emphasizing ownership paired with action and learning.

00:00 Welcome and Friday Vibes

01:06 Craig Adams Background

01:51 Builder Mindset and Growth

03:05 Why Me Why Now

05:39 AI Finds Risk Faster

07:19 From Detection to Remediation

09:53 Completing the Workflow

13:36 Roadmaps in Rapid Change

15:52 Hiring for Curiosity

20:24 Humans Still Do Analysis

22:56 Disruption and Services Future

25:41 Mission Driven Teams

30:32 Repetition and Culture

33:19 EQ Over IQ Leadership

AI’s Impact on Cybersecurity: SOC Automation, GRC Limits, and the Rise of Boutique Advisory

Tom welcomes cybersecurity veteran Dave Cronin, founder of Mission Security and vCISO/Head of Cyber Services with CyberTrust Massachusetts, who recounts his path from technical roles and teaching ethical hacking to senior leadership and nuclear compliance work across U.S. power plants.

They discuss AI as a pivot point in cybersecurity, accelerating both defense and attacks, including uncovering long-standing vulnerabilities. Dave argues AI is rapidly replacing repetitive SOC/MDR Level 1 triage tasks, contributing to consolidation, while human judgment remains critical for response actions and for gray-area domains like GRC where politics and control tradeoffs matter.

They cover market pressures from private equity, ROI scrutiny, workforce cuts, and CISO role changes, alongside increased demand for go-to-market, customer success, and relationship-driven services. Dave advises embracing AI, learning prompting, specializing skills, and he describes helping small organizations and municipalities with compliance needs such as CMMC.

00:37 Dave Cronin Background

02:10 Nuclear Compliance Stories

04:51 Ethical Hacking Roots

06:10 AI Finds Old Flaws

06:31 SOC Automation Impact

11:12 Human Relationships Matter

13:23 GRC and AI Limits

14:59 AI ROI and Cost Cuts

17:37 CISO Role Shifts

20:56 Future of MDR Vendors

22:37 Anthropic and Legal Disruption

23:28 AI for Legal Tasks

24:51 Who AI Disrupts Next

25:08 Future Proof Security Roles

26:21 Go To Market Surge

26:49 Human Service Comeback

28:24 Career Advice Embrace AI

29:36 Prompting and Learning Tools

31:27 AI Clones and Trust

33:54 Day Job Mission Security

35:04 CMMC Compliance Reality

38:42 Small Teams with AI

40:15 Layoffs and AI Washing

42:09 CISO Pay Compression Risks

43:02 Closing Thoughts

In this Cybersecurity Recruiter podcast episode, Thomas chats with Dale Hoak, a former US Navy veteran who transitioned to the commercial sector and progressed from to senior director and now Chief Security Officer/CISO at RegScale.

Dale explains that leaving the military is difficult because individuals must take ownership of healthcare, career planning, compensation negotiation, and resume-building, recommending an exit strategy starting two years before separation and seeking early help (including AI tools) while understanding one’s individual value.

He credits his advancement to strong networks and mentors, hard work, and learning to understand business value and communicate cyber risk in non-technical terms to leaders and boards, using approaches like threat modeling and risk scoring. He discusses AI as a helpful but fallible tool requiring fact-checking, emphasizes continuous learning.

Dale recommends as a starting point "The 7 Habits of Highly Effective People" and then progressing on to 2 series of books by Gary Hayslip. He listens to lots of podcasts

including New CISO and CISO Tradecraft.

00:00 Welcome and Introductions

00:36 Dale’s Career Snapshot

02:08 Life as a CSO

03:06 Leaving the Military

05:00 Certs Resumes and Value

07:31 First Civilian Break

08:51 Networking as a Superpower

10:05 How Promotions Happen

13:20 Building Business Awareness

17:03 Speaking Board Level Risk

17:40 Books and Daily Routines

18:26 AI Needs Human Communication

19:51 Phone Calls and Real Talk

21:18 Using AI Responsibly

22:15 AI Resumes and Hiring Reality

23:29 Culture Fit and Honesty

25:06 Never Stop Learning

27:11 Learning Resources and Creativity

30:26 AI Accelerates Skill Gaps

32:22 Leadership Lessons and Quotes

33:21 Books Podcasts and Wrap Up

Chris Tjotjos on building businesses through crashes, advisory boards, and compounding growth

Thomas chats with Chris Tjotjos on the Cybersecurity Recruiter podcast about his career from sales to leading Logos Communications and later co-founding Promithia and Simvay Systems

Chris describes early entrepreneurial “full throttle” focus, reinvesting profits for years, and the power of compounding, including examples using pennies and leveraged real estate and recurring revenue.

He recounts major disruptions - post-1999 internet implosion after buying out his partner and the 2008 crisis, and how transparency, profit-sharing via an EBIT plan, and shifting customer concentration helped stabilize and grow. A key turning point was meeting entrepreneur Jack Kale, starting an advisory board, and using book-based learning to reshape culture.

Chris explains being approached to sell Logos to Black Box, scaling the division, and critiques lack of synergy in acquisitions. Book recommendations mentioned include "Financial Freedom" Mark Harrelson, "The Vital Difference," and "Leading From The Heart," by Jack Kale, "Rockefeller: The Titan," and "The 38 Letters Rockefeller Wrote to His Son."

00:00 Welcome and Setup

00:39 Meet Chris Tjotjos

01:58 Focus Then Scale

03:04 Early Entrepreneur Grind

04:34 Compounding Mindset

06:55 Leverage and OPM

09:27 Life After the Exit

13:22 Dotcom Crash Lessons

15:29 Open Books EBIT Plan

17:39 Jack Kale Book Club

22:26 Partnership Synergy

23:33 Faith Prayer Meditation

25:31 Perspective and Mortality

26:12 Greek Roots and Big Questions

27:20 Faith Over Wealth

27:50 Servant Leadership in Business

28:12 Why Logos Was Founded

32:26 Selling After the 2008 Storm

36:55 Acquisition Lessons and Synergy

38:54 Starting Again With Promethea

40:18 Advisory Boards That Scale

43:51 Building the Board and Jack Story

47:53 Closing Reflections and Thanks

48:27 AI as a Virtual Board

49:42 When to Form a Board