IT Support Engineer - Remote Role at Underdog

About the Role

Join Underdog as an IT Support Engineer and help us make sports more fun! In this remote IT Support Engineer position, you will play a vital role in our rapidly growing company, which has recently been valued at $1.3 billion. As part of our team, you will not only keep the lights on but also advocate for technology solutions that enhance our internal operations. You will be instrumental in transforming manual tasks into streamlined, automated workflows that support our scaling workforce.

What You'll Do

• Act as the initial point of contact for hardware, software, and access requests across our fully distributed team, ensuring efficient resolution of issues with a high standard for response time and quality.
• Build and maintain automations and AI workflows using tools like Okta Workflows, n8n, OpenAI, and Claude to streamline provisioning, requests, and routine operational work.
• Execute end-to-end onboarding and offboarding workflows in collaboration with our People team, including account provisioning/deprovisioning, Google Workspace account management, and SaaS access management.
• Manage the lifecycle of Mac and Windows devices through Kandji and Jumpcloud MDM, overseeing procurement, enrollment, configuration, app deployment, and compliance enforcement.
• Administer identity and access management in Okta, including SSO configuration, group management, and SCIM integrations.
• Support IT security initiatives, including endpoint compliance and access audits, in partnership with the Security/Technical Compliance team.
• Identify inefficiencies, document processes, and create self-service resources to 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 administering Okta (SSO, MFA, lifecycle management, group/policy configuration) is a must-have.
• Experience managing macOS and Windows devices at scale using an MDM platform (Kandji and Jumpcloud preferred).
• Proficiency in building automations using Okta Workflows, scripting (Bash/Python), and API integrations.
• Working knowledge of Google Workspace administration (user management, OUs, Groups, GAM is a plus).
• Strong customer service instincts and clear written communication skills.
• Comfort working in a security-conscious environment with exposure to access audits and compliance standards.
• A proactive mindset focused on continuous improvement.

Nice to Have

• 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.
• Okta Certified Administrator or similar IT certifications.

What We Offer

• Unlimited PTO for full-time employees, with flexibility around the NFL season.
• 16 weeks of fully paid parental leave.
• Home office stipend to support your remote work setup.
• A connected virtual-first culture with a highly engaged distributed workforce.
• 5% 401k match, FSA, and company-paid health, dental, and vision plan options for employees and dependents.
• Opportunities for relocation support to help you move and settle into your new role.

As a remote-first company, we value in-person connections and expect team members to gather 2-3 times per year for team and company offsites, trainings, and more. If you are passionate about technology and want to join a fast-growing sports company, apply now to become our next IT Support Engineer remote team member!