Principal Enterprise Systems Engineer

Role Overview

As a Principal Enterprise Systems Engineer at Cboe, you will lead the architecture, engineering, and delivery of enterprise infrastructure solutions that power both internal operations and customer-facing platforms. You will solve complex technical challenges, design resilient and scalable systems, and drive modernization across hybrid and multi-cloud environments.

This role carries broad, senior-level responsibilities in infrastructure leadership, cross-functional collaboration, and enterprise transformation. You will define and execute infrastructure strategy, align technology investments with long-term business goals, and serve as a technical authority across the team.

• Define and drive the enterprise infrastructure strategy and roadmap, aligning investments with business objectives and compliance requirements
• Architect scalable, secure, and resilient systems across hybrid and multi-cloud environments, including Windows Server, VMware, Microsoft 365, and Azure
• Establish and govern engineering standards for automation, monitoring, configuration management, and disaster recovery across the team
• Build and maintain AI-assisted workflows using tools such as Claude Code or GitHub Copilot, enabling faster IaC development, automated documentation, and intelligent incident response
• Design and deploy AI agent pipelines for operational tasks: incident triage, configuration drift detection, Jira workflow automation, and runbook generation
• Champion automation and observability at scale using PowerShell, Graph API, Terraform, Ansible, and AI agent frameworks
• Lead incident response and learning review analysis for critical infrastructure events; drive systemic improvements from findings
• Mentor senior and staff engineers, promoting innovation, accountability, and continuous growth
• Oversee vendor and partner relationships, including solution evaluation and contract negotiation
• Represent infrastructure engineering in executive forums, audits, and strategic planning sessions
• Participate in on-call rotation

Requirements

The ideal candidate has:

• Minimum 10 years of experience in enterprise infrastructure engineering, with at least 3–5 years operating at a principal or staff engineer level
• Deep expertise across Microsoft Cloud technologies: Microsoft 365, Intune, Exchange Online, Defender for Endpoint, Azure AD, and Azure infrastructure
• Strong knowledge of Windows Server (2016–2025), Active Directory, DNS, DHCP, GPO, DFS, SQL Server, and VMware vSphere
• Proven experience with infrastructure-as-code tooling: Terraform, Ansible, and PowerShell automation at scale
• Experience with vulnerability management platforms (Microsoft Defender, Conditional Access) and certificate lifecycle management
• Demonstrated experience designing and operating disaster recovery and high-availability architectures using tools such as Rubrik
• Experience building or operationalizing AI-assisted engineering workflows, LLM agent pipelines, or agentic automation frameworks (strongly preferred)
• Track record of mentoring engineers and influencing technical direction across a team or organization