Jason Kozak

Technology lead for a multi-site Alaska distributor with offices in Alaska, Washington and Oregon and remote village stores in rural Alaska: off the road system, reached by small plane, with satellite internet and often no cell service, where every install depends on planning, shipping and staging everything ahead. I design, build and run the full stack: multi-site network, identity and security, helpdesk, intranet, backups and monitoring. I led the company's AI adoption program and built its security awareness program. I use AI the way a good manager uses a team: clear jobs, written rules, independent checks, and a human making the calls. Before that, I spent nine years in enterprise information security at a Fortune 500 insurer, including PCI audits. I document systems so others can run them.

1. Mar 2026 – now

   Senior Technology Strategist · R&D and IT group, multi-site Alaska distributor

   • Led the company-wide AI adoption program: chose the platform, set up single sign-on access, wrote staff safety rules and cost controls, and grew usage from 5 to 11 seats.
   • Host weekly AI training sessions: 24 since May 2026, with 14 staff taking part.
   • Became the project manager the company didn't have on payroll. The village-store project tracker lived in one person's personal drive and had fallen out of date; I moved it to a shared team site, repaired 252 broken formulas in its dashboards, set the weekly meeting to record automatically, and built a Wednesday digest that flags overdue tasks, blockers and trips without booked travel before the meeting starts.
   • Automated summaries for every meeting I attend: each transcript is summarized, then a second, independent AI checks the summary against the transcript and notes anything missed before it posts. Nobody takes notes and nobody proofreads.
   • Run a one-person IT department with the output of a small team: seven AI agents, each with a defined job (coordination, engineering, documentation, review), working under written rules and an approvals log, with an independent reviewer that checks work before anything ships. They do the legwork; I make the decisions.
   • Stood up a private AI server running open-weight models for coding, speech-to-text, image and video generation, and bulk text work. Routine work runs in-house at no per-use cost, and company text never leaves the company. It transcribes ten minutes of audio in under eight seconds.
   • Run an unrestricted open-weight model for authorized penetration testing and security assessments of the company's own systems, for the work commercial AI declines. Access is limited to three named people with their own keys, every use is recorded in a tamper-evident log, staff tools refuse it, and the model was verified against its published hash and tested before use.
   • Building an AI social media agent for customer outreach on the company Facebook page. It drafts posts in the company voice and a person approves each one before it goes out.
   • Built a shared work queue where colleagues donate spare AI capacity to company jobs, and a daily brief that puts every open ask, ticket and promise in one morning email.
   • Built the security awareness program: one reporting channel for phishing and fraud, and a monthly staff newsletter built on real attacks against the company.
   • Took over with no security awareness program and few security controls in place. Closed real gaps one at a time; the Microsoft Secure Score rose from 61% to 70% in three months as a result, never as the target.
   • Built a dashboard that shows all 23 backup jobs (servers, NAS, Microsoft 365 and point-of-sale vaults) and their status at a glance, with alert emails that fire only when a job fails, so every alert is actionable, not noise. The page turns red when its own data goes stale, so a silent failure can't pass for a healthy night.
   • Built an AI usage telemetry pipeline (OpenTelemetry into OpenSearch and Grafana) with a privacy split the owner signed off on: usage metrics on the dashboard, prompt content sealed. It once went quiet for four weeks before anyone noticed, which says less about the monitoring than about the audience: AI was brand new at the company and the user base was me. I fixed and backfilled it, and reported exactly which dates were gone for good.
   • Moved six sites onto one hub-and-spoke SD-WAN in an 18.5-minute planned window; new sites now join with no outage.
   • Lead the PCI DSS program: automatic encryption of card numbers in outbound email, a clean card-data discovery scan and an evidence-based readiness tracker.
   • Built a single sign-on intranet with department workspaces and a 251-page wiki of runbooks and SOPs in under four months.
   • Moved inbound mail to MTA-STS enforcement alongside DKIM, DMARC and data-loss prevention; replaced a commercial password manager with self-hosted vaults.
   • Stood up monitoring for 18 network devices across five sites, a SIEM and a self-hosted helpdesk with SLA targets.
2. Dec 2024 – Mar 2026

   IT Consultant · same company, contract

   • Network segmentation and security projects, a point-of-sale installation at a remote Alaska village store, and staff training.
   • Found Digits, an AI-native accounting platform, and brought it to leadership as a QuickBooks replacement; the company's CPA firm adopted it too. Now on the integration team.
3. From Apr 2023

   Independent IT Consultant

   • Secured shared computers for property offices, point-of-sale terminals and a server for a local business, and supported individual clients.
4. 2006 – 2015

   Information Security Analyst III · Fortune 500 insurance company

   • Owned the network intrusion detection and firewall platforms; managed firewall policy for corporate and PCI requirements.
   • Led external PCI audits for firewall and intrusion detection controls; handled alerts and incidents with an MSSP, SIEM and central logging.
5. 2001 – 2020

   Earlier roles

   • Enterprise desktop and remote support at the same insurer, retail computer technician, and retail store operations management.

AI operations

Multi-agent workflows with independent review, local open-weight models (Ollama, Whisper, image and video generation), Claude administration, staff training, safety rules, cost controls

Security

Microsoft 365 Conditional Access, Intune, Defender, DLP, SIEM, DKIM/DMARC/MTA-STS, security awareness

Compliance

PCI DSS program management, card-data discovery, audits

Networking

UniFi SD-WAN, site-to-site and staff VPN, firewall policy, high availability, monitoring

Systems

Windows Server, Remote Desktop Services, Hyper-V, Proxmox, Linux, Apple Business Manager

Service management

Helpdesk and SLAs, knowledge base, runbooks and SOPs

Project management

Shared trackers, Gantt dashboards, weekly status digests, meeting recording and summaries

Automation

Python, PowerShell, Microsoft Graph, SharePoint, Teams

Strategy

IT roadmapping, vendor management, cost optimization, technology evaluation

Field work

Remote Alaska site installs, point-of-sale and network support

• B.S., Information Systems Security, ITT Technical Institute (fully online program). Graduated with Honors, 4.0 GPA, completed while working full-time in enterprise IT.
• A.A.S., Electronic Engineering / Computer Maintenance and Networking, Lorain County Community College. Dean's List.
• CompTIA Network+ · CompTIA A+ · Microsoft Certified Desktop Technician (MCDST) · Microsoft Certified Professional (MCP)