The Top 5+ Cybersecurity Mentors (2025-2026)
Discover the top Cybersecurity Mentors in 2025-2026. Expert coaches with proven success in delivering cybersecurity advice to applicants and companies alike.
Posted October 5, 2025
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Breaking into cybersecurity calls for precise guidance from people who’ve actually built in the field. The mentors below bring hard-earned expertise from places like Microsoft, Intel, McKinsey, the FBI, translating complex realities into clear career moves. This curated list spans backgrounds and coaching styles so you can find the right fit for your goals and identity. See all our coaches here.
Kevin T.
Experience: Kevin brings 8+ years of cybersecurity experience across Microsoft, PwC, and Cognizant. As a Microsoft Security Consultant, he helps clients navigate complex security challenges and implement practical strategies.
Specialties:
- Breaking into cybersecurity
- Security problem-solving for clients
- Translating complex security topics into clear actions
If you want industry-informed coaching with zero fluff, Kevin’s background at top tech firms is a strong match. He’s especially effective for professionals who need to clear with tangible steps and accountability. Expect focused guidance on what actually moves the needle in interviews and on the job.
"I can’t thank Kevin enough for his help in reviewing and updating my resume. His attention to detail, insightful feedback, and expertise made a huge difference in presenting my experience in the best possible way. He took the time to understand my background and career goals, ensuring my resume was not only polished but also tailored to highlight my strengths effectively. His suggestions were spot-on, and I feel much more confident applying for opportunities now. I highly recommend Kevin to anyone looking for professional and thoughtful resume assistance!"
- Jennifer D., Coached by Kevin and landed a role at Amazon
→ Book a free intro call with Kevin
Julie C.
Experience: Julie’s career spans 20+ years across federal and private sectors including the FBI, Deloitte, McKinsey, BlueCross BlueShield, and even CISO roles. She’s coached 100+ clients on career planning, interview prep, and resume development.
Specialties:
- Career strategy for public and private sector roles
- Leadership development
- Interview preparation and resume optimization
- Building security programs in regulated environments
Candidates seeking senior mentorship will benefit from Julie’s perspectives and FBI-to-Fortune 100 toolkit. She blends business acumen with technical credibility, making complex environments feel navigable. If you need to position your experience for competitive teams, Julie offers the kind of strategic rigor that accelerates careers.
"I am pleased to recommend Julie as a transformative coach and leader in the field of cybersecurity. As a direct impact of her leadership, I was able to successfully navigate the complex intersection of cybersecurity, strategy, and risk management, ultimately landing my first cybersecurity role as a Business Intelligence Manager at GlaxoSmithKline. Her approach to coaching goes beyond technical knowledge—it’s about helping professionals like myself understand how cybersecurity and risk management can align with broader business objectives. This holistic perspective has been instrumental in my role, where I focus on bridging the gap between business-focused security and the central security and risk function. I am incredibly grateful for Julie’s guidance, and I believe her coaching is a key reason I’ve been able to excel in this role. Her leadership in the cybersecurity field is unparalleled, and anyone fortunate enough to work with her will be greatly impacted by her expertise, vision, and mentorship."
- Tina G., Coached by Julie and landed a role at GlaxoSmithKline
→ Book a free intro call with Julie
Bryan L.
Experience: Bryan is a cybersecurity professional, educator, and mentor with experience in AI Red Team operations at Microsoft. He holds 20+ cybersecurity certifications, and has coached 500+ clients.
Specialties:
- Cybersecurity Certification prep
- Career pivots into cybersecurity
- Resume, LinkedIn, and interview coaching
- Hands-on training: AI penetration testing, SOC/IR, cloud (Azure), GRC
If you want a structured, results-focused plan from topics like certification strategy to mock interviews, Bryan brings it. He excels with career changers, transitioning veterans, and practitioners looking to move up quickly. His breadth (AI security to compliance) and track record (500+ clients, 20+ certs) make him a strong guide for both technical upskilling and applicants looking to land offers.
"I’d like to express my deepest gratitude to Bryan Leon for his exceptional mentorship throughout my career journey. His guidance was instrumental in helping me bolster my resume and develop the skills to critically assess my own resume and LinkedIn profile—a level of self-sufficiency that proved invaluable in my job search. Thanks to Bryan’s expertise, I secured an internship at Microsoft. His coaching didn’t stop there—throughout my internship, he provided strategic guidance on how to maximize my time, ensuring I made the most of the experience. His insights helped me stand out, ultimately leading to a full-time offer at Microsoft. Beyond resume and interview preparation, Bryan also assisted me in reviewing my offer letter and negotiating terms, equipping me with the confidence and knowledge to make the best long-term decision for my career. Bryan’s mentorship goes beyond just landing a job—he focuses on sustainable career growth, setting up his mentees for long-term success. If you're looking for a coach who delivers real results and helps you take control of your career trajectory, I highly recommend working with Bryan."
- Carolina B., Coached by Bryan and landed a role at Microsoft
→ Book a free intro call with Bryan
Michael C.
Experience: Michael is a cybersecurity leader and educator with a Doctorate in Cybersecurity & Information Assurance. As a Business Information Security Officer at Stanley Black & Decker, he leads framework implementation. He’s coached 18 professionals into the field.
Specialties:
- Cybersecurity implementation and compliance
- Breaking in from non-traditional backgrounds
- Clear instruction on core security concepts
- Career growth planning rooted in real leadership experience
Michael’s journey from entry-level tech support to six-figure cybersecurity leadership resonates with learners who value grit. He’s particularly helpful for anyone who wants practical guidance and a mentor who’s walked the path. Expect straightforward plans, patient teaching, and measurable progress.
"Dr. Chambers brings years of valuable insight and experience into the classes I've had the pleasure to take under his instruction. He takes the concepts presented in the lesson plan and gives them real world, practical application via stories he tells of relevant situations. His insights into the industry make it much easier to grasp and remember what is taught in the classes."
- Nicholas S., Coached by Michael
→ Book a free intro call with Michael
Alex K.
Experience: Alex is a Cyber News Magazine “Top 40 Under 40” Cybersecurity Expert with 8+ years leading global operations and risk programs at companies like Intel and Deloitte. She has also helped lead dark web and cybercriminal investigations.
Specialties:
- Cyber threat intelligence
- Executive briefings and stakeholder alignment
- Enterprise risk programs
- Scaling security operations
For candidates pursuing CTI, Alex brings a rare end-to-end perspective. She’s adept at turning intelligence into measurable business outcomes. If you want to speak the language of both analysts and the C-suite, Alex is a powerful guide.
→ Book a free intro call with Alex
Matthew R.
Experience: Matthew has 35+ years as a Chief Information Security Officer, including 24 years at Intel, where he commanded the cyber crisis response team. He’s now CISO at Mercury Risk and Compliance and advises companies, universities, and governments worldwide.
Specialties:
- Cybersecurity leadership and design
- Enterprise strategy, governance, and value measurement
- Emerging threats, digital ethics, and regulatory risk
Leaders who need a seasoned strategist will find exceptional value in Matthew’s counsel. He’s skilled at translating risk into business decisions and building organizations that scale. If you’re preparing for leadership interviews or establishing a security function, Matthew’s playbook is incredibly helpful.
"Matt has seen it all! His contributions to Intel have been profound, and he has helped drive strategy into action. We are a more secure world with Matt's expert observations and contributions in all the forums he has so aptly served over the past decade+. Should you find yourself in a position that requires expertise around governance, risk and compliance, Matt should be one of your go-to counselors. I highly recommended his services and urge anyone who has not met him to reach out and start a dialogue."
- Jeff Towle, Coached by Matt
→ Book a free intro call with Matthew
Richard W.
Experience: Richard is a large-enterprise CISO with 30 years in IT. He’s hired and coached talent across public, VC-backed, and private companies.
Specialties:
- Career transitions from IT into cybersecurity
- Interview preparation and promotion strategy
- Privacy, compliance, and security leadership
- Cross-industry security program oversight
If you’re moving from IT to cybersecurity or aiming for your next promotion, Richard’s hiring and coaching experience makes the path clearer. He knows what leaders prioritize and how to position your impact across regulated industries. Mentees will find an empathetic coach who pairs practical advice with concrete steps to stand out.
"Richard has played a significant role in shaping my career in information security. As a coach, mentor, and trusted advisor, he has provided invaluable guidance throughout my journey. His deep expertise and broad knowledge enable him to offer practical, well-informed advice in a wide range of situations. Beyond his technical acumen, Richard is an exceptional communicator and a genuinely great person, making every interaction insightful and enjoyable. "
- Jason S., Coached by Richard
→ Book a free intro call with Richard
Find the Best Coach for Your Cybersecurity Journey
The fastest way to progress in cybersecurity is with targeted, expert guidance customized to your background, goals, and the roles you’re pursuing. Explore the coach profiles above and book a free 15-minute intro call to see who’s the best fit, or browse all coaches here.
Not sure where to start? Schedule a free strategy and coach-matching call with the Leland team, and we’ll help you pick the right mentor for your next move. Find the right coach and start building your cybersecurity career today.
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Top Cybersecurity Coaches – FAQs
How do I know if I need a cybersecurity mentor versus just getting certifications?
- Certifications are valuable, but they don’t always teach you how to position yourself for roles or navigate the job market. A mentor can show you how to turn certifications into real opportunities.
What should I look for when choosing a cybersecurity mentor if I want to move into a leadership role?
- If you’re aiming for management or executive positions, look for mentors with CISO experience or who have built security programs in large organizations. They’ll help you shift from focusing only on technical depth to also mastering executive communication.
Can a mentor actually help me land my first cybersecurity job without prior industry experience?
- Yes, mentors often work with career changers and early-career professionals. They can help you build a portfolio, highlight transferable skills, and prepare for interviews so hiring managers see you as a viable candidate even without specific cybersecurity experience.
