Jason Cassella.

IT Operations EngineerNew York, NY

About

IT operations professional specializing in automation, identity and access management, and endpoint engineering.

I lead on-site IT for DraftKings' NYC office and build the tooling that takes repetitive work off the queue: AI agents that research and resolve tickets, self-service routing for common requests, and guardrails that keep access changes safe.

Selected work

AI-powered IT knowledge platform

Problem
Answering “have we seen this before?” meant minutes of manual ticket digging.
Built
An MCP server indexing 234K+ tickets and ~900 knowledge articles so AI agents can investigate, resolve, and document tickets.
Result
Research time from ~5 minutes to under 1.
  • Python
  • MCP
  • SQLite
  • REST APIs

Ticket automation

Problem
Repetitive requests (MFA resets, mail rule changes, self-service redirects) waited in the queue for a human.
Built
Event-driven handlers that triage, reply to, and resolve common request types end to end, with a ledger to track every action.
Result
144 tickets handled in the first three weeks, 89 resolved automatically.
  • Python
  • REST APIs
  • Slack

RBAC validation guardrails

Problem
Role-based access requests were slow to prepare and easy to get wrong.
Built
A PowerShell validation tool adopted across IT that blocks prohibited group assignments before they are made.
Result
Prep time down 58%, from 12 minutes to 5, across 270+ requests.
  • PowerShell
  • Active Directory
  • Entra ID

Enterprise AI rollout

Problem
Hundreds of employees needed access to Claude for Enterprise without granting it to departed or disabled accounts.
Built
A scripted, dry-run-first provisioning run with terminated- and disabled-account safeguards, plus hands-on Claude Code and MCP setup for individual teams.
Result
969 employees across 17 departments provisioned in one run.
  • PowerShell
  • Active Directory
  • Claude
  • MCP

Email security review

Problem
Junk mail complaints rose sharply after an email security platform migration.
Built
A Microsoft Defender for Office 365 configuration review with Microsoft and InfoSec, and a phased rollout plan with pilot groups, change management, and rollback steps.
Result
Microsoft’s top findings turned into a pilot-first rollout plan with rollback steps for every phase.
  • Defender for Office 365
  • Exchange Online
  • PowerShell

At DraftKings, 2025–2026

tickets resolved
2,700+
access requests
1,100+
high-priority incidents
550+
tickets auto-resolved in 3 weeks
89

Experience

Senior IT Services Technician

DraftKings · New York, NY

May 2025 – Present

  • Sole on-site IT lead for DraftKings’ NYC office, supporting 70+ employees across macOS, Windows, iOS, and AV.
  • Administer Jamf, Intune, Entra ID, and Microsoft 365 across identity, device compliance, and endpoint security; own hardware lifecycle from procurement to secure decommissioning.
  • Own access provisioning, revocation, and RBAC governance workflows.
  • Build internal automation and AI tooling (see Selected work) and enable non-technical teams with Claude Code and MCP.

Service Desk Analyst

Star Group LP · Woodbury, NY

Apr 2023 – May 2025

  • Provided enterprise IT support for 900+ employees across Windows endpoints, Microsoft 365, identity, network connectivity, and SaaS applications.
  • Administered Active Directory and Entra ID user accounts, security groups, and access permissions, resolving authentication and access issues.
  • Delivered white-glove technical support for C-level executives and senior leadership.
  • Provisioned and deployed Windows workstations using MDT, including imaging, configuration, domain enrollment, and software deployment.
  • Troubleshot DNS, DHCP, VPN, endpoint connectivity, and hardware issues, escalating infrastructure problems when required.
  • Mentored junior analysts on internal systems, support procedures, troubleshooting, and escalations.

Education

SUNY Oneonta

B.S. Computer Science · 2017 – 2020

Skills

Endpoint
JamfIntunemacOSWindowsLinuxiOS
Identity & Security
Entra IDActive DirectoryOktaRBACMFAConditional AccessDuoConductorOneExchange OnlineDefender for Office 365
ITSM & Collaboration
FreshserviceZoom RoomsGoogle WorkspaceMicrosoft 365Slack
Automation & AI
PowerShellPythonClaude CodeMCPSQLiteREST APIs