Note: The job is a remote job and is open to candidates in USA. OpenSesame is transforming workforce development through an AI-powered marketplace of skill-building courses and learning pathways. The Systems Administrator supports and improves internal IT systems by resolving escalated issues, administering core tools, and driving automation, integrations, access management, and security initiatives. The role also owns systems projects and process improvements that enable secure and reliable AI-powered workflows.
Responsibilities
- Meet with the IT Manager to understand team priorities, success metrics, and upcoming projects
- Review OpenSesame’s existing IT infrastructure, including cloud environments and SaaS platforms, and demonstrate the ability to speak to their functions and interdependencies
- Shadow IT Support Specialists to observe ticket workflows and identify support-related bottlenecks or recurring issues
- Shadow the Systems Administrator to learn OpenSesame’s tool setup, user administration practices, and system documentation
- Complete all onboarding and internal training required for IS tools and systems
- Successfully assist with and resolve at least two active project tasks assigned by the current Systems Administrator
- Independently manage and resolve escalated IT support tickets within expected service timelines
- Complete at least three project assignments independently from start to finish
- Demonstrate working proficiency in Jamf, Google Workspace, and Okta, with an emphasis on endpoint management and user access controls
- Begin maintaining enterprise data and internet security practices, including documentation updates and enforcement of established policies
- Carry a full ticket and project workload equivalent to team peers, delivering consistent and timely resolutions
- Participate in the cross-training of Help Desk Support personnel on key internal systems and applications
- Demonstrate admin-level proficiency in three additional IT tools under the IS team’s purview
- Identify and introduce an AI-driven or automation-based solution to improve a repetitive internal process
- Actively contribute to upcoming internal security compliance audits by preparing systems documentation and responding to audit requests
- Audit existing account provisioning and deprovisioning workflows; recommend and present a plan to streamline these processes
- Identify at least two manual workflows for automation, and lead their technical evaluation and implementation
- Identify opportunities to strengthen the reliability, security, and maintainability of internal AI workflows through improved automation, system integrations, and access management
- Demonstrate full ownership of all tools and applications within the IS environment through a performance review with IT leadership
- Transition into autonomous operations, confidently managing support tickets, systems projects, and process improvements with minimal oversight
Skills
- Review OpenSesame's existing IT infrastructure, including cloud environments and SaaS platforms, and demonstrate the ability to speak to their functions and interdependencies
- Demonstrate working proficiency in Jamf, Google Workspace, and Okta, with an emphasis on endpoint management and user access controls
- Demonstrate admin-level proficiency in three additional IT tools under the IS team's purview
- This position can be based anywhere in the US
- We operate as a remote-first company, and invest in mandatory all-company meetings several times a year in addition to required team travel as necessary
- All positions can be based anywhere in the US, and require up to 15 days of travel per year, with senior management and leadership teams requiring up to 35 days
- We're looking for self-starters with a proven track record of delivering excellent results
Benefits
- Comprehensive medical, dental, and vision coverage
- Flexible PTO
- 401(k) matching
- Incentive stock options
- Volunteer time off
- Employee Resource Groups
- A generous professional development program with dedicated annual time off for learning and growth
- Remote-first work arrangement
- Hands-on training and clear guardrails to experiment responsibly with AI tools
Company Overview