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.

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.

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

Underdog Fantasy

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