Direct Access
Focused advisory sessions for founders, investors, and technology leaders who need an experienced enterprise security executive's perspective on AI accountability, cybersecurity, enterprise trust, product strategy, and market positioning.
Each session is a focused, candid conversation. Pick the format that fits your need.
You have one specific question and need a straight answer. Pressure-test a decision, get a read on a pitch or positioning, or sanity-check a direction before you commit.
The core session for founders, product leaders, and investors. Get an enterprise buyer’s perspective on your product, pitch, GTM approach, or market, or an operator’s read on a company or category you’re evaluating. Enough time to go deep on one topic and leave with valuable insights and clear takeaways.
An extended working session for complex questions: enterprise positioning, governance strategy, product direction, or diligence support. We work the problem together and you leave with a clear plan for what to do next.
All sessions are private video calls. If you would like materials reviewed before the call, send them at least 48 hours in advance.
Send a short note describing who you are and what you want to cover. If it's a fit, I'll point you to the right session. If it isn't, I'll tell you that too. I would rather turn away a booking than waste your money on the wrong conversation.
Check Fit Before Booking
Greg Crowley is a former enterprise CISO, founder of Runtime Executive, and author of Secure AI Enablement: A CISO's Practical Guide to Governing AI at Scale. He has spent 25+ years on the enterprise side of the table: building security programs, evaluating vendors, and sitting through the pitches, diligence calls, and board conversations you are preparing for.
Explore the BookThese sessions are built for founders, product leaders, and GTM teams at AI and cybersecurity companies who need an honest, informed enterprise perspective.
Whether you are pressure-testing a pitch, validating product direction, sharpening competitive positioning, or trying to understand how enterprise buyers actually evaluate what you are selling, this is a direct line to someone who has been on the other side of that conversation for over two decades.
For investors, these sessions serve the same purpose as an expert-network call, booked directly: an operator's perspective on companies, categories, and markets in cybersecurity and AI, without an intermediary in the middle.
