Underdog Fantasy

IT Support Engineer

Underdog Fantasy

full-time

Posted on:

Location Type: Remote

Location: United States

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Salary

💰 $90,000 - $112,500 per year

Tech Stack

About the role

  • Serve as the initial point of contact for hardware, software, and access requests across our fully distributed team, triaging and resolving issues efficiently with a high standard for response time and quality.
  • Build and maintain automations and AI workflows using tools like Okta Workflows, n8n, OpenAI, Claude and similar platforms to streamline provisioning, requests, and routine operational work.
  • Execute end-to-end onboarding and offboarding workflows in partnership with our People team, including account provisioning/deprovisioning, Google Workspace account management, SaaS access grants and revocations, and enterprise fleet management.
  • Manage Mac and Windows device lifecycle through Kandji and Jumpcloud MDM: procurement, enrollment, configuration, app deployment, compliance enforcement, and secure wipe/retrieval.
  • Administer identity and access management in Okta, including SSO configuration, group management, and SCIM integrations.
  • Support IT security initiatives including endpoint compliance, access audits, and Device Trust enforcement in partnership with the Security/Technical Compliance team
  • Identify inefficiencies, document processes, and build self-service resources that scale IT operations as the company grows.

Requirements

  • 2–4+ years of hands-on IT Support, Systems Administration, or IT Engineering experience, preferably in a remote-first or distributed environment.
  • Extensive experience in administering Okta (SSO, MFA, lifecycle management, group/policy configuration) — this is a must-have.
  • Working experience administering macOS and Windows devices at scale using an MDM platform (Kandji and Jumpcloud strongly preferred).
  • Working experience in building automations using Okta Workflows, scripting (Bash/Python), and API integrations to streamline provisioning, offboarding, and recurring IT operations.
  • Working knowledge of Google Workspace administration (user management, OUs, Groups, GAM is a plus).
  • Strong customer service instincts and clear written communication — you’re someone teammates trust to solve their problems quickly and keep them informed.
  • Comfort working in a security-conscious environment with exposure to access audits, compliance standards, and endpoint security tooling.
  • A proactive, continuous-improvement mindset — you look for root causes, document what you learn, and reduce repeat issues over time.
Benefits
  • Unlimited PTO for full-time employees (we're extremely flexible with the exception of the first few weeks before & into the NFL season)
  • 16 weeks of fully paid parental leave
  • Home office stipend
  • A connected virtual-first culture with a highly engaged distributed workforce
  • 5% 401k match, FSA, company paid health, dental, vision plan options for employees and dependents
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
IT SupportSystems AdministrationIT EngineeringOktamacOSWindowsMDMBashPythonGoogle Workspace
Soft Skills
customer servicewritten communicationproactive mindsetcontinuous improvementproblem-solvingtrustworthinessefficiencydocumentationscalabilitycollaboration