Cybersecurity leadership · Advisory · Speaking
I'm Lee Bailey, a former CISO with more than 20 years in cybersecurity leadership. I advise executive teams, speak on cyber leadership and help the next generation of security leaders grow into the role.
Free 30-minute call · Virtual or on-site · United States
Board briefing
● Open questions
01
02
03
Your board is already asking these questions. I help you answer them with confidence.
20+
Years in cybersecurity leadership
CISO
Former chief information security officer
75+
Leadership and security guides published
3
Ways to work together: advisory, speaking and leadership development
The leadership gap
Gap 01
The board hears acronyms, not business risk. Budgets stall, and security gets treated as a cost instead of a decision.
Gap 02
Incidents test judgment, not tools. Without a practiced plan, teams freeze, scatter or wait for someone else to call it.
Gap 03
Security becomes the department of “no”. Policies get written, but the culture that actually stops attacks never forms.
Ways to work together
Every engagement starts with the same question: what decision do you need to make, and what's stopping you from making it well?
01 — Advisory
Cyber governance, risk ownership, security program transformation and board reporting, so your leadership team decides with a clear view of the risk.
For executive teams and boards that need an experienced security voice in the room.
02 — Development
Coaching and mentoring for security professionals stepping into leadership, from first-time managers to aspiring CISOs.
For aspiring CISOs, new security managers and the organizations growing them.
03 — Speaking
Keynotes, panels and workshops on cyber leadership, governance and resilience that leave audiences with decisions to make, not just facts to remember.
For conferences, leadership offsites and executive training days.
How it works
Step 01
Thirty minutes on your situation and goals, with an honest answer on whether I'm the right fit.
Step 02
Scope, outcomes and timeline in writing, so you know exactly what you're getting before we start.
Step 03
Coaching sessions, workshops or advisory work, with regular check-ins to keep momentum.
Step 04
Progress you can point to in front of your board, your team and yourself.
In their words
“
If you are looking for an engaging, knowledgeable speaker, I highly recommend Lee. His ability to tackle subjects critical to leadership and technology is unique and dynamic, especially cybersecurity leadership.
Marina O'Rourke
Franchise Growth Strategist
“Lee is a dynamic and knowledgeable presenter on technology and leadership, especially cybersecurity leadership. I walked away with one or two nuggets I could use. I highly recommend him for any speaking engagement!”
Alexis Gallagher · Vice President, Tandym Group
“As a manager his focus on staff development creates a loyal and knowledgeable staff. Lee's work ethic, management skills, and IT knowledge would make him a tremendous asset to any organization.”
Andrew Warrner · Senior Account Executive, Technology & Professional Development Training
“Lee is a talented, engaging speaker. His manner makes you feel comfortable and open to hear what he has to say.”
Paul Simkins · Leadership Speaker & Trainer, Ah-Ha! Moments Learning
At a glance
20+ years
Building and leading cybersecurity and IT programs
Former CISO
Accountable for security at the executive table
Advisor · Speaker · Mentor
Executive advisory, keynotes and leadership development
Meet Lee
I'm Lee Bailey. I've spent more than 20 years building and leading cybersecurity programs, including serving as a CISO.
I started LeadingCyber to share what that work actually takes: thinking clearly about risk, explaining it to the people who fund it, and leading teams through pressure. Today I advise leadership teams, speak at industry events and mentor security professionals on their way up.
Insights
Risk & governance
How to identify, assess, treat and monitor cyber risk in language your board understands.
Leadership
When a fractional security leader makes sense, what they should deliver and what it costs to get wrong.
Threats
Why senior leaders are the most valuable target in your company, and how to make them a hard one.
Start with a conversation
Book a free 30-minute discovery call. You'll leave with a clearer picture of your biggest risk and the first move to make.
