IT Support Engineer

Underdog Fantasy is a rapidly growing company in the sports industry, focused on enhancing the experience for sports fans through innovative products. The IT Support Engineer role involves being a key player in supporting the internal growth by managing IT support requests, automating workflows, and ensuring efficient onboarding and offboarding processes.

Responsibilities:

• 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
• Experience with CrowdStrike or similar security tooling
• Familiarity with Linear, Freshservice, Jira, or similar ITSM/ticketing platforms
• Experience with identity governance concepts (least privilege, RBAC, JIT access)
• Experience running SaaS license audits and access cleanup projects
• Exposure to Workday or HRIS integrations with identity platforms
• Experience in a high-growth environments
• Okta Certified Administrator or similar IT certifications