Director-Level Security Leadership • System Security Engineering • AI & Platform Security

I lead security engineering programs that make complex, high-consequence systems safe to operate at scale.

I’m Jason Grob - a CISSP-certified cybersecurity and system security engineering leader. I own portfolio-level security initiatives, lead cross-functional teams through ambiguity, and translate architectural risk into executive-ready decisions. My focus is building durable security programs that scale with the business.

Portfolio ownership • cross-functional leadership • executive communication
What I Do

Security leadership that scales delivery - not just controls

I lead security work that ships: aligning teams, clarifying risk, and building guardrails that make delivery faster and safer. My focus is outcomes leadership can trust - across architecture, lifecycle, and operations.

System Security Engineering (SSE)
Architecture & lifecycle
  • Security-by-design through the full lifecycle (requirements → architecture → verification → ops)
  • Threat modeling + control mapping that produces decision-ready priorities
  • Dev/test/prod patterns that make secure operation repeatable in complex environments
High-assurance engineering Risk-driven controls Lifecycle security
Security Leadership & Enablement
People & programs
  • Partner with engineering and product so security accelerates delivery instead of blocking it
  • Translate risk into action leaders can prioritize (plain language, clear tradeoffs, measurable outcomes)
  • Develop people and culture: mentoring, standards, and feedback loops that raise the whole team
Director-level leadership Cross-functional alignment Executive communication
AI / Advanced Tooling Security
Data, models & usage
  • Define usage guardrails in sensitive environments
  • Establish audit-ready patterns for identity, logging, and approvals that don’t break velocity
  • Enable experimentation safely with clear constraints that match mission and policy
AI/ML security Usage governance Data protection
Enterprise-Style Homelab & Testing
Hands-on validation
  • Run an enterprise-style testbed to validate architectures (segmentation, identity, DNS, and observability)
  • Prototype operational controls (DNS policy, logging, SIEM readiness, failover) before production equivalents
  • Document decisions and tradeoffs like a real program: standards, runbooks, and repeatable patterns
Architecture validation Operational hardening Security monitoring
Experience & Impact

Projects, systems, and outcomes I’ve led

This is a high-level view for technical and organizational leaders.

Selected themes
  • Shaping security plans for AI and advanced tooling in environments with DoD/DoE-level sensitivity.
  • Bringing system security engineering discipline into organizations whose tooling outgrew their guardrails.
  • Designing and operating an enterprise-style homelab that mirrors real-world production constraints.
System Security Engineering & Cybersecurity
Security architecture & engineering leadership in high-consequence environments
  • Worked on federal programs where confidentiality, integrity, and availability are truly mission-critical.
  • Aligned engineering teams, security requirements, and system constraints into coherent architectures.
  • Contributed to cost-aware, risk-aware decisions that respected both mission and budget.
Proof-of-execution
Security plan for AI & tooling
Governance & guardrails

Developing a comprehensive, living security plan for AI/ML and advanced tools in a high-sensitivity engineering environment, focused on:

  • Environment separation (dev/test/prod) and zero-trust access to models, data, and tools.
  • Least-privilege access, auditable workflows, and clear accountability for usage.
  • Preventing data leakage while still allowing engineers to innovate.
Enterprise-style homelab build
Architecture & operations

Built a homelab to mimic enterprise operations, including:

  • Virtualized infrastructure with centralized identity, role separation, and policy-based access controls
  • Segmented network services with hardened name resolution, traffic isolation, and auditability
  • Roadmap for security monitoring, log aggregation, and controlled administrative access.

Note for readers: I’m happy to map these experiences directly to your architecture, risk posture, and roadmap in a conversation or technical deep-dive.

Homelab & Labs

A controlled environment to pressure-test security decisions

My lab environment isn’t a hobby setup - it’s a structured system for validating security architecture, operational tradeoffs, and failure modes before they reach production environments. I use it to practice what I expect teams to live with: segmentation, layered controls, identity-first design, and systems that are observable, supportable, and resilient under stress.

Core lab design
Modeled after real enterprise environments
  • Segmented network domains representing management, trusted users, workstations, servers, test systems, and remote access.
  • Centralized identity and access controls with role separation, policy enforcement, and auditable change paths.
  • Layered name resolution and traffic control services, each with a clearly defined responsibility and failure boundary..
Zero-trust-friendly layouts DNS and identity as first-class controls Defense in depth
Security & observability roadmap
Intentional evolution, not tool sprawl
  • Incremental introduction of centralized logging and security monitoring to support detection, triage, and post-incident analysis.
  • Designing controlled administrative access paths that enable emergency response without undermining segmentation or least privilege.
  • Evaluating intrusion detection and prevention placement with attention to signal quality, operational overhead, and cost.
Why this matters for you
  • I test ideas in a controlled environment before recommending them to teams or leadership.
  • I understand the day-two realities of operating segmented networks, identity systems, and security controls - not just the design diagrams.
  • I speak from lived operational experience, not just policy language or vendor slideware.

In short: if I recommend a security design, it’s one I’d be willing to run, debug, and be accountable for myself.

About

Builder first, security leader always

I see security as an engineering discipline: deeply practical, grounded in reality, and always connected to the mission.

I’ve spent my career working on complex systems where the stakes are high and the tolerance for hand-wavy security is low. I’m comfortable moving between:

  • Big-picture architecture and system risk discussions with leadership.
  • Hands-on debugging of DNS, VLAN, or identity issues in the weeds.
  • Coaching engineers toward a systems-thinking mindset about security.

My goal in the next phase of my career is clear: step fully into security leadership – Director-level and beyond – while staying close enough to the technology to keep decisions honest.

What it’s like to work with me
Day-to-day
  • Direct, honest communication – no fear-mongering, no jargon for its own sake.
  • Strong bias toward clarity, documentation, and repeatable processes.
  • Respect for constraints: budget, politics, timelines, and legacy systems.
Quiet consulting
Advisory, by fit

While my primary focus is on full-time leadership roles, I occasionally advise organizations on:

  • System security engineering strategy and roadmapping.
  • Secure introduction of AI/ML and LLM tooling into existing environments.
  • Designing realistic homelab/test environments for internal teams.

If that sounds like a fit, reach out and we can discuss whether it makes sense.

Contact

Let’s talk about your systems and security roadmap

If you’re exploring senior security engineering or Director-level roles, or you want to discuss advisory work, I’d be glad to connect.

For hiring managers & leaders
Full-time roles

I’m particularly interested in roles that combine:

  • System security engineering with architecture and leadership.
  • Responsibility for AI/ML, advanced tooling, or complex infrastructure.
  • Space to build clear processes and mentor strong technical teams.

The best way to reach me is via email or LinkedIn.

I’m happy to provide a full CV, detailed project breakdowns, or references on request.