Remote Senior Systems Administrator - Chicago

Who We Are

At Firstup, our mission is to improve the employee experience at every moment that matters, large and small. As the communication pipeline for the world's workforce, we now serve 40 of the Fortune 100 companies, reaching and connecting more than 17 million employees daily.

Our employees are experts in the employee experience, workforce communications and technology. 

Joining Firstup means joining a movement to make work better for every worker. As the world's first intelligent communication platform, Firstup meaningfully engages employees at every moment from hire to retire, and delivers engagement insights to help companies support, promote and retain their talent. Our movement has taken root and is evident in our world-class customer base. Now we need your help. Ready to make a difference in the world?

Reporting to the Director of Technology, the Senior Systems Administrator is responsible for ensuring the reliability, security, and continuous improvement of the organization's enterprise technology environment. As a fully remote role supporting a globally distributed workforce, this position owns and manages core infrastructure services, identity and access management, endpoint management, SaaS platforms, and security and compliance initiatives. The role plays a key part in delivering a seamless technology experience for employees worldwide while driving operational excellence and scalability across the IT landscape. 

This role serves as a senior technical owner across endpoint management, identity and access management, collaboration platforms, enterprise SaaS applications, and workplace technology initiatives, balancing operational excellence with strategic technology improvements.

Candidates will be located in the Chicago area.

Responsibilities

• Administer and support Google Workspace, MS Teams, Zoom, Slack, and associated collaboration technologies.

• Manage platform configuration, security settings, licensing, integrations, and lifecycle management.

• Manage the full lifecycle of corporate endpoints across macOS and Windows environments, including provisioning, deployment, support, and retirement.

• Administer Jamf, BeyondTrust, Microsoft Intune, and related endpoint management and security platforms.

• Administer Okta and related identity management services, including SSO, MFA, lifecycle management, and application integrations.

• Manage user provisioning, deprovisioning, access reviews, and role-based access controls.

• Administer and maintain Google Workspace, Microsoft 365, and associated enterprise systems.

• Monitor system health, performance, availability, and capacity, proactively identifying and resolving issues.

• Lead implementation, migration, and enhancement projects across enterprise technology platforms.

• Develop project plans, technical designs, implementation strategies, and operational transition plans.

• Ensure systems and services comply with corporate security policies and industry standards, including SOC 2 and ISO 27001.

• Support security audits, vulnerability remediation, and compliance initiatives.

• Act as a senior escalation point for complex technical issues affecting employees globally.

• Collaborate with internal teams and external vendors to deliver technology projects and operational improvements.

Required Qualifications

• Proven expertise in Apple/macOS environments, Google Workspace, and Jamf device management.

• Experience managing enterprise endpoint platforms, device lifecycle processes, patching, configuration standards, and asset management programs.

• Strong understanding of identity and access management, including Okta, SSO, MFA, conditional access policies, user lifecycle management, and access reviews.

• Experience administering cloud-based SaaS platforms, including user provisioning, configuration, integrations, lifecycle management, and governance.

• Demonstrated experience implementing and maintaining security controls, endpoint protection, compliance initiatives, and enterprise security best practices.

• Experience supporting a remote-first or globally distributed workforce.

• Proficiency in scripting and automation using Bash, Python, PowerShell, or similar technologies.

• Strong documentation skills, including technical standards, operational procedures, and knowledge base content.

• Excellent communication and interpersonal skills, with the ability to explain technical concepts clearly to technical and non-technical audiences, including business stakeholders.

• Analytical problem solver with a root-cause mindset and a focus on scalable, long-term solutions.

• Proactive and self-motivated, with strong ownership, accountability, and collaboration skills.

• 5+ years of progressive experience in systems administration, enterprise IT, endpoint management, or related infrastructure roles.

Preferred Qualifications

• Experience with network administration and diagnostics, including Aruba, Palo Alto, and Zscaler technologies.

• Experience supporting cloud infrastructure platforms such as AWS, Azure, or Google Cloud Platform.

• Experience with Microsoft Intune, Microsoft 365, BeyondTrust, virtualization platforms, or similar enterprise technologies.

• Experience evaluating, deploying, or governing enterprise AI solutions, including ChatGPT, Gemini, Claude, or related technologies.

• Bachelor's degree in Information Technology, Computer Science, or a related discipline, or equivalent practical experience.

• Relevant certifications such as Jamf Certified Administrator, Google Workspace Administrator, Okta Certified Administrator, Palo Alto Networks, Microsoft, or equivalent certifications.

$125,000 - $140,000 a year

Firstup expects the base salary for this role to be between $125,000-$140,000. The starting rate of pay may vary based on factors including, but not limited to, position offered, location, education, training, and/or experience.

Why Firstup?

Because you care - about people, the work you do, and the connections you make. Work is such a large part of life; it only makes sense to make it awesome.

If you want to engage brilliant minds in a high-growth and inclusive environment where ideas are rewarded regardless of who they come from, join us. This is a rapidly changing space so if you thrive on ambiguity, are hungry for a challenge, and have the guts to speak your mind, you could be a perfect fit.

We offer an excellent PTO program, great health benefits, a casual and friendly environment, remote work, and a leadership team who truly believes in your growth – both personally and professionally.

Firstup is committed to providing equal employment opportunities to all applicants for employment and to all employees, without regard to race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, protected disability, veteran status, or any other protected status in accordance with applicable federal, state or local laws.

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We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.