Available for hire · San Francisco Bay Area

IT OperationsManagerwho ships production AI tools.

12+ years scaling enterprise infrastructure at high-growth tech companies. Most recently IT Operations Manager at a NASDAQ-listed tech company. 900 employees, fully remote, 6 years, 4 promotions.

Download ResumeLinkedIn
900+
Users Supported
550
Devices Migrated
200+
SaaS Platforms
98%
CSAT · 3 Yrs Straight
$500K+
Vendor Contracts Owned
6 YRS
NASDAQ-Listed · LIF

Selected Work

Built, not just managed.

PythonLive

IT Helpdesk Triage Agent

AI-powered triage tool that categorizes, prioritizes, and routes IT support tickets in batch. Built on the same logic used to manage 5,000+ tickets/year across a 900-person org.

GitHub↓ more
PythonLive

SaaS Spend Auditor

Enterprise SaaS portfolio intelligence tool. Ingests 50+ vendor records, runs AI categorization via Claude, and surfaces spend waste, security gaps, and renewal risk across 4 audit tabs.

GitHub↓ more
PythonLive

IAM Access Review Tool

5-module identity governance tool covering new hire provisioning, cross-app access review, AI violation detection, offboarding, and SOX audit reports — for a simulated 50-person org.

GitHub↓ more
PythonLive

Okta Integration Auditor

Audits Okta app integrations for dormant, misconfigured, and high-risk apps. Connects to live Okta API or runs in demo mode with 20 realistic sample apps.

GitHub↓ more
PythonLive

SOC2 Readiness Suite

Full-lifecycle SOC2 Type I/II readiness assessment tool — gap scoring across all 59 controls and all 5 Trust Services Criteria, 12 data source connectors, Claude-powered policy generation, Supabase snapshot persistence, and drift detection.

GitHub↓ more
PythonLive

HIPAA Readiness Agent

Full-lifecycle HIPAA Security Rule assessment tool — gap scoring across all 42 controls (Administrative/Physical/Technical), BAA inventory tracking, SOC2 crosswalk analysis, and Claude-generated phased remediation roadmap.

GitHub↓ more
PythonLive

GWS Security Auditor

Audits a Google Workspace tenant across 6 security dimensions and produces a prioritized finding report. Demo mode runs against a synthetic 200-person org — no credentials required.

GitHub↓ more
PythonLive

Slack IT Ops Bot

Automates IT operations directly in Slack — three slash commands handle ticket triage, access request routing, and incident response. Claude-powered, with Jira integration, Confluence KB search, and interactive Approve/Deny workflows.

GitHub↓ more
PythonLive

IT Budget and Vendor Renewal Tracker

Per-seat cost modeling, renewal date tracking, and budget vs. actuals dashboard across a 45-vendor SaaS portfolio. Built to demonstrate $500K+ contract ownership for IT Director and SAM roles.

GitHub↓ more
PythonLive

JSM Configurator

Design your Jira Service Management configuration before you build it — request types, SLA tiers, automation rules, and escalation paths, with Confluence-ready export.

GitHub↓ more
PythonLive

HRIS Lifecycle Designer

Designs Joiner/Mover/Leaver automation flows for HRIS → identity platform → downstream apps. Live flow diagram preview and production runbook export.

GitHub↓ more
PythonLive

MDM Migration Planner

Generates fully dynamic MDM migration plans. Phase structure, wave count, and durations change based on source/target platform, device count, team size, and urgency — not just the numbers.

GitHub↓ more
PythonLive

GitHub EMU Toolkit

Compliance audit tool for GitHub Enterprise Managed User orgs. Surfaces outside collaborators, public repos, team permissions, and app installations in a single dashboard.

GitHub↓ more
PythonLive

Incident Postmortem AI

Generates structured incident postmortems from a plain-language description. Outputs executive summary, timeline, 5-Why root cause chain, action items with owners, and prevention measures.

GitHub↓ more
Python

Okta MCP Server

Read-only MCP server that exposes Okta identity data to Claude via the Model Context Protocol. 14 tools across users, groups, apps, and policies. Demo mode runs on Apex Labs fixture data with no credentials required.

GitHub↓ more
Claude MCP

Technical Intake Skill

25-question adaptive client interview system for Claude. Calibrates to the client's technical level mid-conversation, detects goal drift, and produces 5 structured outputs.

No public repo↓ more
Python

NetWatch

Lightweight network monitor and auto-repair tool for Apple Silicon Macs. Detects Wi-Fi drops, DNS failures, gateway issues, and packet loss — then fixes them automatically.

GitHub↓ more
React

Derelict Command

Retro-futuristic tactical extraction roguelike built with WebGL. Procedurally generated space stations, A* pathfinding AI, Bresenham line-of-sight raycasting, and fog of war.

GitHub↓ more
Python

OEM Hunter

Automotive parts procurement agent that scrapes 18+ sources via 14 plugins. Non-LLM, pure signal — WAF bypass via Camoufox, direct scraper orchestration across dealer networks.

GitHub↓ more
Python

OpenTaxes

Tax document parser purpose-built for real-world malformed PDFs — Fidelity 1099-B dot-leader formatting, 2-digit year dates, and edge cases that break commercial tools.

GitHub↓ more
Android

JST TXT

Clean, secure SMS/MMS replacement for Android. Encrypted local storage, no telemetry, no bloat — built as a drop-in replacement for Samsung Messages.

GitHub↓ more

Core Stack

Platforms I run at depth.

🔐

Identity & Access

  • Okta (SSO / MFA / OIG)
  • Lumos
  • RBAC / SCIM
  • AWS IAM
  • Atlassian Guard
💻

Device Management

  • Microsoft Intune
  • Jamf Pro
  • Kandji
  • VMware Workspace ONE
  • LogMeIn Central
☁️

Cloud & Infrastructure

  • Google Workspace
  • GCP / Firebase
  • AWS
  • Azure / O365
  • GitHub EMU
⚡

AI & Automation

  • Anthropic Claude
  • OpenAI / ChatGPT
  • Google Gemini
  • MCP Servers
  • Slack Bots + APIs
🤝

ITSM & Collaboration

  • Jira Service Management
  • Confluence
  • Slack Enterprise Grid
  • Salesforce
  • Box
🛡️

Security & Compliance

  • SOX Audits
  • FINRA / SEC
  • RBAC Design
  • Access Reviews
  • Change Management
Certifications
Google Workspace Administrator
Okta Certified Administrator
Proofpoint Certified Administrator

Contact

Let's talk.

Open to IT Manager, IT Director, and IT + AI hybrid roles.

ostrutsovski@gmail.comlinkedin.com/in/olegst