Senior IT Services Technician

Jason Cassella.

New York, NY

About

Senior IT professional specializing in endpoint management, identity and access administration, and workflow automation. Sole on-site IT lead for DraftKings' NYC office, supporting a primarily macOS environment alongside Windows, mobile, and AV systems. I build AI-assisted automation that makes IT faster and more secure.

Selected impact

01 / 02

RBAC Validation Tool

PowerShell · WinForms · Active Directory

GUI tool, adopted by the entire IT team, that validates access requests against live Active Directory before provisioning. It skips invalid security groups, then drafts the ticket note and user reply.

10 min → <5 min

per ticket · Recognized by Compliance

Freshservice MCP Server

Python · MCP · SQLite · Freshservice API

Read-only MCP server that lets Claude Code search our full Freshservice history in plain English. A local full-text index covers ticket descriptions and replies, which the Freshservice API can't search.

5 min → <1 min

to find past fixes · Plain-English search

Experience

Senior IT Services Technician

DraftKings · New York, NY

May 2025 — Present

  • Sole on-site IT lead for the NYC office, supporting 70+ employees across macOS, Windows, iOS, and AV
  • Administer Jamf, Intune, Entra ID, and Microsoft 365 for identity, device compliance, and endpoint security
  • Build PowerShell automation for identity lifecycle, M365 administration, and endpoint management
  • Drive adoption of AI tools including Claude Code across the organization
  • Own the end-to-end hardware lifecycle, from procurement through secure decommissioning
  • Provision and maintain RBAC across internal systems and SaaS platforms

Service Desk Analyst

Star Group LP · Woodbury, NY

Apr 2023 — May 2025

  • Enterprise IT support for 900+ employees across Windows, macOS, M365, and SaaS
  • White-glove executive support for C-level staff
  • Managed AD accounts, group policies, and MDT workstation deployments
  • Mentored junior analysts

Education

SUNY Oneonta

B.S. Computer Science · 2017 — 2020

Skills

Endpoint
JamfIntunemacOSWindowsLinuxiOS
Identity & Security
Entra IDActive DirectoryRBACMFAConditional AccessConductorOne
AV & Collaboration
Zoom RoomsGoogle WorkspaceMicrosoft 365Slack
Automation & AI
PowerShellPythonClaude CodeMCPSQLiteFreshservice API