Systems Administrator

About OpenSesame

OpenSesame is transforming workforce development with an AI-powered marketplace of skill-building courses and learning pathways. We help organizations build skills and stay compliant through a high-quality content catalog, seamless LMS/LXP integrations, and advanced capabilities like skills-based curation and multilingual content creation. More than 2,000 companies, including 150+ of the Global 2000, rely on OpenSesame to develop the world's most productive and admired workforces.
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About the Team

At OpenSesame , the Information Systems team empowers employees with the tools and systems to deliver exceptional customer service. We maintain key business platforms, streamline operations through automation, and enhance the employee experience through cross-functional collaboration.
About the Role

The Systems Administrator supports and improves OpenSesame ’s internal IT systems, resolving escalated issues, managing core tools, and driving automation and security initiatives. This role is ideal for someone proactive and hands-on, ready to take ownership in a fast-paced environment. The role will also help build, administer, and improve the internal systems, integrations, permissions, and automation that enable secure, reliable AI-powered workflows across the business.
Performance-Based Objectives
Within 30 Days

- 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.

Within 60 Days

- 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.

Within 90 Days

- 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.

Within 120 Days

- 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.

Tech Stack

- OKTA

- Apple Macbook

- Google Workspace (GSuite)

- Jira

- Confluence

- Zoom

- Mi