Systems Administrator
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.