IT Operations Engineer

Keystone AI® is the leading AI GRC platform for the Enterprise, helping governance, risk, and compliance teams limit surprises, strengthen resilience, augment program performance, and confidently quantify impact and business value. Built to provide a centralized view of risk and compliance, with AI intelligence woven into the platform's core, Keystone AI delivers real-time insights and actionable data to help drive current business decisions, with the flexibility to scale alongside evolving business needs. Recognized as a Leader in the GRC Market, Keystone AI continues to further solidify its position as a best-in-class platform. At Keystone AI, our people are the foundation of everything we do. We are committed to delivering an exceptional experience for our employees and our customers by empowering and enabling our people to take ownership, make an impact, and deliver their best work. Chicago, IL (Hybrid) At Keystone AI, we recognize that exceptional talent comes in all shapes and forms, and that there is no such thing as a 'perfect' candidate. The qualifications below represent the core competencies, skills, and experiences that align most closely with the day-to-day responsibilities of this role - if you don't check every single box and are excited about this work, we still highly encourage you to apply. About the Role The IT Operations Engineer serves as a primary technical driver of Keystone AI’s internal technology ecosystem, responsible for hands-on administration, lifecycle automation, and maintenance of our cloud infrastructure. Acting as the functional anchor for our SaaS stack, you will design integrations and secure our endpoint fleet to drive operational efficiency across the business. Because this role sits at the intersection of multiple departments, success hinges on exceptional collaboration and a polished communication style. You excel at breaking down sophisticated systems architecture and technical concepts into approachable, straightforward insights, and will routinely translate technical data into executive-ready reports that guide priority alignment and update senior leadership on infrastructure progress. What You’ll Do Architectural Maintenance: Own and continuously improve Keystone AI’s IT infrastructure at a foundational level—including endpoint management (Jamf), identity services (Okta), SaaS stack integrations, and zero-trust network access controls (Zscaler). Lifecycle Automation & Administration: Design, implement, and maintain advanced automation (via Python, Bash, Okta Workflows, or Zapier) to streamline RBAC frameworks, automated user provisioning (including Paylocity sync), and entitlement reviews. Cross-Functional Initiatives: Execute high-impact corporate IT operations projects end-to-end, including MDM policy deployment, SaaS license consolidation, and automated access review programs. Security & Identity Governance: Partner closely with InfoSec to manage secure authentication architectures (SAML, SCIM, JIT, OAuth), audit SaaS access control policies, and ensure strict compliance with least-privilege principles. Infrastructure Support: Maintain and troubleshoot critical backend architecture, including AWS VDI workspaces and hosted SCIM bridges on Google Cloud Platform (GCP). Emerging Technology & AI Enablement: Evaluate and implement AI powered productivity solutions, workflow automation, and emerging technologies that improve employee experience and operational efficiency while maintaining security and governance standards. HQ Technology Operations: Provide support for Chicago HQ technology operations, service as an escalation resource for office infrastructure, conference room technology, networking, and onsite employee support when needed. What You Bring Required Proven Domain Experience: 3+ years of experience in IT operations, systems administration, or systems engineering, demonstrating hands-on administration of enterprise cloud environments and project delivery. Identity & Network Security Expertise: Okta Certified Professional or Administrator designation and expertise in advanced Okta administration- including SSO, MFA, profile mastering, attribute mapping, and directory integrations with core apps (Paylocity, Google Workspace, Atlassian, and 1Password)- alongside cloud network security platforms like Zscaler ZIA. MDM & Endpoint Mastery: Strong working knowledge of macOS environments and Jamf MDM fleet management at scale, including custom configuration profiles, software deployment, and compliance enforcement. Automation & Scripting Proficiency: Adept at building logic-driven integrations using tools like Okta Workflows or platform APIs to eliminate manual tasks. AI Literacy & Curiosity: Active interest or hands-on experience in utilizing AI productivity tools (e.g., ChatGPT, Claude, Gemini) to optimize code output, accelerate troubleshooting, and safely drive administrative efficiencies. Nice to have Certifications: Jamf 200/300. Google Workspace Administrator. Cloud Inf