AI Engineering · Infrastructure Architecture · Team Leadership

Hi, I'm Chris Woolard

Senior technology leader with 15+ years of enterprise IT experience across AI engineering, hyperconverged infrastructure, and software development — from datacenter strategy and team building to production AI pipelines and shipped software products.

15+
Years Enterprise IT
5+
Hypervisor Platforms
3
Games in Development
~/portfolio $ whoami
chris woolard — ai engineer & infrastructure lead
~/portfolio $ cat expertise.txt
▸ Enterprise IT Architecture & Strategy
▸ AI Engineering / LLMs / Generative AI
▸ Hyperconverged Infrastructure (5 platforms)
▸ Distributed Storage (ZFS / Ceph / GlusterFS)
▸ Team Leadership & Mentorship
▸ Software Dev (Godot / Flutter / Python)
~/portfolio $ status
● Open to New Opportunities
👨‍💻

Strategic leader.
Deep technical roots.

I'm a senior technology leader with over 15 years of enterprise IT experience — starting at the helpdesk in 2011 and growing into architecture, engineering leadership, and AI strategy. Currently leading multiple engineering teams at a large healthcare organization, responsible for enterprise identity, authentication infrastructure, and platform operations at scale.

Outside of my day job, I run a fully self-managed homelab environment — multi-platform hypervisors (Proxmox, Hyper-V, XCP-NG, bhyve, UnRAID, VMware), distributed storage (ZFS, Ceph, GlusterFS), containerized services, custom networking with VLAN segmentation and SSL inspection, and AI pipeline experimentation.

I'm also co-founder of Dog Water Development, an indie game studio with multiple titles in development for Steam and mobile.

  • Peoria, AZ — Available Remote & On-site
  • MBA in IT Management · BS in Information Technology — WGU
  • U.S. Army Veteran · IT Specialist (25B)
  • chris@teamwoolard.com
  • github.com/virtiz
  • Steam Developer — Dog Water Development

Core competencies

🏢 Leadership & Strategy

Enterprise Architecture Team Building Technology Roadmapping Hiring & Mentorship IT Governance Vendor Management Cost Optimization Cross-functional Leadership

🤖 AI & Machine Learning

LLMs (GPT-4 / Claude / Gemini) AI Pipeline Architecture RAG / Retrieval Systems GitHub Copilot ComfyUI / Stable Diffusion AudioCraft LangChain OpenAI API Generative Media AI-Augmented Development

🖥️ Hypervisors & Virtualization

Proxmox VE XCP-NG / Xen Orchestra Hyper-V + WSFC VMware ESXi / vSphere UnRAID FreeBSD bhyve GPU Passthrough Live Migration VM Snapshots & Replication

💾 Storage & Data Architecture

ZFS (30-disk pools) Ceph Distributed Storage GlusterFS TrueNAS SCALE CSV / iSCSI / SMB SLOG / L2ARC DFS Namespaces Large-Scale RAID

🔐 Networking & Security

OPNsense / pfSense VLAN Segmentation WireGuard VPN Squid Proxy + SSL Bump AdGuard / Split-Brain DNS Cloudflare Zero Trust Active Directory / GPO Uptime Kuma Monitoring

🌐 DevOps & Cloud

Docker / Compose Portainer Nginx / Reverse Proxy Cloudflare Microsoft Azure Python Automation PowerShell Bash / Shell Scripting REST API Integration

⚙️ Development

Godot 4 / GDScript Unreal Engine C# / .NET Flutter / Dart Python TypeScript Lua SQL

Selected Projects

A cross-section of infrastructure builds, AI work, and software products. Each project reflects real-world decision-making, architecture ownership, and hands-on delivery.

View All Projects

Let's work together

I'm open to new opportunities. If you're building or scaling a team that needs someone who bridges deep technical execution with strategic thinking — let's talk.

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