What I Offer
Most cybersecurity careers stall not because of a skills gap but because of a visibility gap — the right people don’t know what you’re capable of, or you’re building toward a role that doesn’t actually exist the way you imagine it. I’ve sat in the rooms where those decisions get made.
I spent thirty years in IT and cybersecurity, including fifteen years in security leadership — as a founder, CTO, VP, and CEO. I’ve hired security professionals, fired them, built teams from scratch, and made the calls about who gets promoted and who gets passed over. That perspective is what I bring to every mentoring engagement.
I work with people at three specific inflection points: breaking into the field for the first time, moving into a security leadership role, and closing the gap between where they are and a promotion that keeps not happening. I don’t do general career advice. Each engagement is built around your situation and where you’re actually stuck.
The thing that separates a mentor with real executive experience from one who’s had a long career as an individual contributor is that I’ve made the decisions on the other side of the table. I know what a hiring manager is actually looking for when they read a security résumé, because I’ve read hundreds of them. I know what gets someone promoted into a CISO role and what gets them quietly skipped over, because I’ve been the person making that call. I know what the first two years of a security leadership role actually feel like, because I’ve lived it and watched people around me succeed and fail at it.
That’s the lens I bring to this work. Not a framework, not a methodology — a specific, tested read on how security careers actually develop inside real organizations.
Live 1:1 Mentoring Session – $500
Monthly Career Mentoring Subscription- $1,500/month
Security certifications fail people in predictable ways — not because the material is too hard, but because they study the wrong things for too long and walk into the exam without a realistic sense of where their gaps actually are. This engagement is structured around fixing that.
Getting promoted into a senior security role or a first management position requires a different argument than doing your current job well. Most people who get passed over aren’t less competent than the people who advance — they’ve just failed to make their impact legible to the people making the decision.
Most security professionals who want to move roles — into a new sector, up into management, or out of a company that’s stopped growing — spend six to nine months longer than necessary because they’re getting generic career advice from people who don’t understand how security hiring actually works.
Have Roger come to speak to your company, gathering or church.