Principal Enterprise Systems Engineer

Insight Global; Lenexa (KS); On-site; USD 170,000 - 210,000; Full time

Job summary

Cboe Global Markets, based in Overland Park, KS, is seeking a Principal Enterprise Systems Engineer to lead architecture, engineering and delivery of enterprise infrastructure across hybrid and multi‑cloud environments. You will define strategy, solve complex challenges and drive modernization while aligning with business goals.

Responsibilities include scalable design, automation, incident response, AI‑assisted workflows, mentoring engineers, vendor management and participation in executive

Qualifications

• The ideal candidate has 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.

Responsibilities

• 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

Skills

Enterprise infra engineering

Microsoft 365 / Azure

Windows Server / Active Directory

Terraform / Ansible / PowerShell

Vulnerability management

Disaster recovery design

AI-assisted engineering workflows

Mentoring engineers

Tools

Terraform

Ansible

PowerShell

Rubrik

Claude Code

GitHub Copilot

Job description

Job Description

Job Description:

Building trusted markets — powered by our people

At Cboe Global Markets, we inspire our people to solve complex challenges together because what we do matters. We provide the financial infrastructure that powers the global economy. As a leading provider of market infrastructure and tradable products, Cboe delivers cutting‑edge trading, clearing and investment solutions to market participants around the world.

We’re building meaningful ways to support professional and personal development while strengthening the trust we’ve earned as a global market leader. Our teams are empowered to share ideas, actively pursue them and bring on a challenge. As champions of internal mobility and access to opportunity, we encourage our people to “go for it” and equip our managers with the training to coach their teams to the next level. We strive to provide employees a safe space to network, share ideas and create opportunities.

Please note: To support strong partnership and team connection, this role follows a four day in office work model in our Overland Park, KS office.

Location Overview

Cboe Global Markets operates a key office in the Overland Park Xchange (OPx), located in Overland Park, Kansas, a bustling suburb of Kansas City. The OPx business park is strategically positioned to provide convenient access to the Kansas City metropolitan area, offering modern infrastructure and a collaborative environment ideal for the financial services and technology industries. This location benefits from proximity to major highways, making it easily accessible for employees

The OPx site provides a balance of high‑quality office space, advanced facilities, and an environment conducive to productivity and growth.

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. You will also champion AI‑assisted engineering practices, including agentic workflows and LLM‑based tooling, to accelerate delivery and reduce operational toil.

Your responsibilities will be:

• 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

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to [e-mail] learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy: https://insightglobal.com/workforce-privacy-policy/.

Skills and 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