Flexible Operating Systems Engineer Jobs in Kansas

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

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

Benefits and Perks of working for Cboe Global Markets
We value the total wellbeing of our people - including health, financial, personal and social wellness. We believe standard benefits like health insurance and fair pay are a given at any organization. Still, you should know we offer:

• Fair and competitive salary and incentive compensation packages with an upside for overachievement
• Generous paid time off, including vacation, personal days, sick days and annual community service days
• Health, dental and vision benefits, including access to telemedicine and mental health services
• 2:1 401(k) match, up to 8% match immediately upon hire Discounted Employee Stock Purchase Plan
• Tax Savings Accounts for health, dependent and transportation
• Employee referral bonus program
• Volunteer opportunities to help you give back to your communities

Some of our associates' favorite benefits and perks include:

• Complimentary lunch, snacks and coffee in any Cboe office
• Paid Tuition assistance and education opportunities
• Generous charitable giving company match
• Paid parental leave and fertility benefits
• On-site gyms and discounts to other fitness centers

More About Cboe Global Markets
We're reimagining the future of the workplace by focusing on what matters most, our people. Our journey is an inclusive one. We're investing deeply in leadership programs and career development initiatives that ensure everyone has an equal chance to succeed.
We work with purpose, solving problems with ingenuity, collaboration, and a lot of passion. We're an engaged and excited team connecting markets across borders and embracing growth in all its forms to achieve incredible outcomes.
Learn more about life at Cboe on our website and LinkedIn.
Equal Employment Opportunity
We're proud to be an equal opportunity employer do not discriminate against any employee or applicant for employment based on any legally protected characteristic, including race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, genetic information, or Veteran status. We are committed to fostering a workplace where all individuals are valued and respected.
#LI-CP2
This position is not eligible for be legally authorized to work in the United States without the need for employer sponsorship now or in the future.
Salary Ranges (applicable for US locations only)
At Cboe, we are committed to providing a competitive, transparent, and market-informed total rewards program. The anticipated base salary range for this role is $148,750-$192,500, with actual compensation determined by job-related factors such as skills, relevant experience, education, internal alignment, and location.
This role may also be eligible for annual incentive compensation and, where applicable, participation in Cboe's long-term equity programs.
Additional information about Cboe's total rewards program, including benefits and other compensation components, can be found here: Total Rewards at CBOE.
Any communication from Cboe regarding this position will only come from a Cboe recruiter who has a @cboe.com email or via LinkedIn Recruiter. Cboe does not use any other third party communication tools for recruiting purposes.