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.
Learn more: www.opensesame.com/about

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
• Microsoft Intune
• JAMF
• Password Manager
• ZScaler

You might notice we don’t have the typical list of requirements and buzzwords here. That’s intentional.

We’re looking for proven examples from your career that show you can do this job, that you’ve built systems, driven alignment, and created impact at scale. When you look back a year from now, you’ll know you’ve made OpenSesame better, faster, and stronger because of your leadership.

Although it should go without saying (but it doesn’t), OpenSesame is an equal opportunity employer and we strive to create a welcoming, inclusive environment that celebrates diversity.

We use AI. For real. Every team at OpenSesame works with AI tools daily, not as a buzzword, but as practice. You'll build fluency that most companies are still talking about adopting, with hands-on training and clear guardrails to experiment responsibly. AI amplifies your creativity and judgment. It doesn't replace them. The skills you build here travel with you.

Location: 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.

Performance-Driven: We're looking for self-starters with a proven track record of delivering excellent results, but we're highly selective about who we hire. We don't focus on typical job requirements, instead, we're interested in specific examples from your past experiences. 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.

Compensation: The base salary for this position typically ranges from $80,000 to $88,000, depending on experience. We carefully consider a wide range of compensation factors, relying on market data to determine compensation and consider your specific job family, background, skills, and experience. We prioritize pay transparency, fairness, and equity to create a positive and inclusive work environment, regularly reviewing our compensation practices to align with our values and goals.

Benefits: Benefits include comprehensive medical, dental, and vision coverage, flexible PTO, 401(k) matching, incentive stock options, volunteer time off, Employee Resource Groups, and a generous professional development program with dedicated annual time off for learning and growth.

Equal Employment Opportunity: OpenSesame is an Equal Employment Opportunity and Affirmative Action employer that values and welcomes diversity. We do not discriminate on the basis of various legally protected characteristics, including criminal history, and strive to provide reasonable accommodations to qualified individuals with disabilities. We prioritize safety and security and may use your information accordingly, and you can contact us for assistance or accommodations during the job application process. 

Pay Transparency: At OpenSesame, we prioritize pay transparency, fairness, and equity to create a positive and inclusive work environment, regularly reviewing our compensation practices to align with our values and goals. We provide competitive and fair compensation to our employees based on their skills, experience, and performance.

CPRA (California Candidates): When you submit your application, OpenSesame may collect and use your personal information in accordance with our privacy policy and the CPRA. This may include personal details and employment history, and will only be used for employment-related purposes. We may share this information with third-party service providers, but we will not sell it to third parties. If you have any questions or concerns, please contact us, and for more information on your rights under the CPRA, refer to our privacy policy or the California Attorney General's website.