Bobby Simpson
Systems · Security · AI · Technical Leadership

Complex systems. Clearer edges.

Senior Systems & Security Engineer

I design, build, and improve systems where infrastructure, security, identity, automation, and organizational complexity meet. My background spans more than 20 years of enterprise technology — from carrier-scale systems engineering and security architecture to long-tenure CIO leadership — with current work in AI grounding, agentic workflows, and human-centered security.

selected technical impact

Work that changed the system.

I tend to be most useful when a problem crosses boundaries: data and permissions, infrastructure and continuity, architecture and operations, or product capability and customer reality.

70%

Faster employee provisioning

Led a two-year Data Revitalization effort aligning people, roles, permissions, data repositories, and automation across a regulated professional-services firm.

<1s

Live backbone migration

Recovered and re-architected a failed dual-Cisco 6509 hospital backbone, moving static routing to OSPF with sub-second production interruption.

17+

Years of technical CIO work

Designed and operated secure enterprise infrastructure, security architecture, continuity, client connectivity, and technical services while leading a seven-person engineering team.

4

National carrier environments

Supported AT&T, SBC, Verizon, and WorldCom/UUNET in carrier-class IP-services engineering, convergence architecture, and QoS across Layer 2/3 networks.

2025 — present / technical R&D

Current work.

Recent projects extend the same systems instinct into AI-assisted engineering, source-grounded knowledge architecture, automation, and trust/security protocols. AI is an extension of the systems career, not a replacement for it.

career spine

Built at several altitudes.

Titles changed. The recurring work did not: understand the real system, make the dependencies legible, reduce unnecessary complexity, and leave something more durable behind.

2025 — present

Independent Technical R&D

AI Systems, Security & Automation

AI-assisted engineering, agentic workflows, source-grounded knowledge systems, trust/security protocols, local-first tooling, static validation, and browser/serverless prototypes.

2007 — 2024

Chief Information Officer

Finley & Cook, PLLC

Hands-on executive and technical leadership for enterprise infrastructure, information security, data/access architecture, resilience, client-facing technical services, and a seven-person engineering team. Data Revitalization reduced provisioning time by 70%, simplified backup/compliance labor, and automated external security-audit responses.

2005 — 2007

Security Architect

Oklahoma Department of Human Services

Enterprise datacenter security architecture, segmentation, IDS, load balancing, HIPAA-aligned reviews, and technical leadership for the Computer Emergency Response Team.

2004

Senior Systems Engineer

iPolicy Networks

Pre- and post-sales engineering for multi-gigabit security appliances: technical discovery, labs, enterprise evaluations, RFI/RFP responses, partner enablement, and solution architecture.

2000 — 2003

Senior Consulting Systems Engineer — IP Services

Lucent Technologies / SpringTide

Carrier-class IP-services systems engineering, lab architecture, large-account support, VoIP/IP Centrex convergence, and QoS for national telecommunications providers.

1998 — 2000

Director of Engineering, Internet & Broadband Operations

Logix Communications

National ATM backbone and broadband engineering, routing architecture, circuit diagnostics, IP allocation, QoS/SLA operations, and voice/data convergence strategy.

Credentials: CISSP · GCIA (Honors) · GCIH (Honors) · GPEN (Honors) · former SANS Mentor Instructor · SANS Advisory Committee · InfraGard

Education: MBA, Information Technology Management · BS, Information Technology — Security · Western Governors University

where I tend to fit

Senior capability. Useful scope.

I am not optimizing for title. I am looking for environments where broad technical experience is useful, the work is real, and responsibility can stay close enough to the system to see whether it actually works.

01

Systems / Security

Senior systems, infrastructure, security, integration, architecture, resilience, and complex troubleshooting roles.

02

Technical Leadership

Small or experienced technical teams where leadership still benefits from architecture depth and direct technical engagement.

03

Solutions Engineering

Complex products and enterprise customers where discovery, technical validation, architecture, and translation matter more than prospecting.

04

AI + Automation

Grounding, agentic workflows, knowledge architecture, integration, and automation where reliability and inspectability matter.

ideas / research / experiments

The stranger edges

Not everything I make is a product, and not every useful idea belongs in a résumé. These are some of the places where I explore trust, continuity, consent, meaning, memory, and human-machine coordination.

professional conversation

Have a real system with a difficult edge?

I am interested in senior engineering, technical leadership, solutions engineering, and AI-enabled systems work where broad technical judgment can create measurable leverage.

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