IT Support Engineer - Underdog Fantasy

At Underdog, we make sports more fun.

Our thesis is simple: build the best products and we’ll build the biggest company in the space, because there’s so much more to be built for sports fans. We’re just over five years in, and we’re one of the fastest-growing sports companies ever, most recently valued at $1.3B. And it’s still the early days.

We’ve built and scaled multiple games and products across fantasy sports, sports betting, and prediction markets, all united in one seamless, simple, easy to use, intuitive and fun app.

Underdog isn’t for everyone. One of our core values is give a sh*t. The people who win here are the ones who care, push, and perform. If that’s you, come join us.

Winning as an Underdog is more fun.

As the IT Support Engineer, You aren’t just keeping the lights on; you are a core player that powers our internal growth. In this role, you will move beyond standard ticket closing to being the technology advocate for our identity solutions and SaaS integrations that support our scaling workforce. You’ll be the face for the entire IT organization, turning manual tasks into streamlined, secured, and automated workflows that allow us to scale securely.

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.

Who you are

• 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 u