IT Support Engineer
WFA Digital Insight
As remote work continues to redefine the modern workplace, demand for skilled IT support engineers has surged. With the rise of distributed teams, companies like Underdog Fantasy are seeking experts who can streamline IT operations, ensuring seamless connectivity and security. The IT support engineer role is particularly crucial in high-growth environments, where efficient technology infrastructure can make or break a company's ability to scale. According to recent trends, the need for professionals with expertise in Okta and IT engineering has grown significantly, with many companies seeking candidates who can automate workflows, manage device lifecycles, and administer identity and access management systems.
Job Description
About the Role
The IT Support Engineer plays a vital role in powering Underdog Fantasy's internal growth by streamlining IT operations and supporting the company's fully distributed team. This involves serving as the initial point of contact for hardware, software, and access requests, as well as building and maintaining automations and AI workflows to enhance efficiency. The successful candidate will be responsible for executing end-to-end onboarding and offboarding workflows, managing device lifecycles, and administering identity and access management in Okta.As a key member of the IT organization, the IT Support Engineer will be expected to identify inefficiencies, document processes, and build self-service resources that scale IT operations as the company grows. Collaboration with the People team and Security/Technical Compliance team will be essential in ensuring that all IT operations are aligned with the company's goals and security standards.
Underdog Fantasy is committed to creating a dynamic and innovative work environment that fosters growth and creativity. As a company that values simplicity, intuitiveness, and fun, the IT Support Engineer will be expected to embody these principles in their work, constantly seeking ways to improve IT operations and support the company's mission.
What You Will Do
- Serve as the initial point of contact for hardware, software, and access requests across the fully distributed team
- 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 partnership with the People team
- Manage Mac and Windows device lifecycles through Kandji and Jumpcloud MDM, including 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
- Collaborate with the People team to ensure seamless onboarding and offboarding processes
- Develop and maintain technical documentation to support IT operations
What We Are Looking For
- 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)
- 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
- Strong customer service instincts and clear written communication
- Comfort working in a security-conscious environment with exposure to access audits, compliance standards, and endpoint security tooling
- A proactive, continuous-improvement mindset
- Experience with Google Workspace administration (user management, OUs, Groups, GAM) is a plus
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 A
Benefits and Perks
- Competitive compensation package
- Opportunity to work with a high-growth company in the sports technology industry
- Collaborative and dynamic work environment
- Professional development opportunities
- Access to cutting-edge technology and tools
- Flexible working hours and remote work options
- Comprehensive health insurance package
- Generous PTO policy
- Employee recognition and reward programs
How to Stand Out
- Ensure you have hands-on experience with Okta and IT engineering, as these skills are crucial for the role.
- Familiarize yourself with the company's products and services to demonstrate your interest and knowledge.
- Highlight your ability to work independently and collaboratively in a remote environment.
- Showcase your problem-solving skills and experience with automation tools and workflows.
- Prepare examples of how you've improved IT operations and supported remote teams in previous roles.
- Research the company's culture and values to demonstrate your alignment with their mission and principles.
- Be prepared to discuss your experience with security-conscious environments and access audits.
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