Director, Network Automation & Tooling

Cboe Global Markets•Chicago, IL

2d•Hybrid

About The Position

Cboe's infrastructure footprint — and the telemetry stream it produces — is growing faster than our headcount can follow. We're hiring the leader who will close that gap with agents and intelligent automation, not more dashboards and runbooks. The Director, Network Automation & Tooling owns the strategy, architecture, and team behind the platform that lets Cboe's Operations and Engineering organizations operate at 10x their current capacity: a centralized Docker/Kubernetes backend hosting a growing fleet of AI agents, built and continuously extended with agentic coding tools such as Claude Code, that automate infrastructure operations across network, security, and telemetry domains. The intelligence layer is central to that mission. This team drives telemetry from across Cboe's global footprint — SNMP, gNMI, syslog, and API-based sources — into our Prometheus and Grafana observability platform, then builds on top of it: threshold alerting and trend analysis, and well beyond them, machine learning and agentic analysis that surface anomalies before they become incidents, correlate signals across domains, and sharpen how Operations and Engineering handle today's events and plan tomorrow's capacity. This is not a traditional infrastructure management role. It demands current technical credibility in container orchestration and infrastructure automation at scale, genuine fluency in emerging agentic AI patterns, and the leadership skill to guide subject matter experts across three domains as they extend an existing agent framework into Cboe's next-generation automation system. Agentic infrastructure engineering is being defined right now, and this leader will help define it at Cboe — setting the vision for how our network adapts to future demand, and carrying that thinking to the network and security teams who build on it and to associates across the firm. It's also hands-on. The Director stays close enough to the technology to review agent architectures, unblock hard problems, and extend the framework personally when it matters most.

Requirements

A track record of conceiving something that didn't exist and then getting it built. Specifically: Original technical thinking that shipped. You identified a problem others were solving with more headcount or more tooling, proposed a fundamentally different approach, and delivered it. Ideally something that put your organization ahead of its peers rather than caught up with them.
Executive partnership, not just executive reporting. You've taken an idea of your own to senior leadership, secured the funding or organizational support to pursue it, and stayed accountable for the outcome. You can point to a system or capability that exists today because you convinced people it should.
Leadership of engineers doing genuinely new work. You've built and led teams operating without established playbooks, where the standards, patterns, and definitions of done had to be invented as you went — and you kept the work disciplined anyway.
Hands-on fluency with Python and API-driven integration. You automate workflows in Python yourself, and you understand in detail how to code against the APIs of firewalls, routers, switches, logging systems, and other common third-party applications.
Hands-on fluency with agentic development. You've personally built with agentic coding tools against real production problems, and you have opinions on where they work, where they fail, and what has to be true before an agent is allowed to touch critical infrastructure.
Comfort being early. This discipline is a few years old. You're drawn to that rather than waiting for it to settle, and you're prepared to be one of the people whose choices set the pattern for everyone who follows.
A minimum of 12 years of progressive infrastructure, automation, or DevOps engineering experience, including a minimum of 5 years in a people leadership role managing software engineering or automation-focused teams.
Deep production experience building and operating modern cloud-native infrastructure — either as a primary builder in AWS (or a comparable cloud platform), or running containerized workloads on Docker and Kubernetes at scale. We expect real depth in one and working fluency in the other. Kubernetes is a significant ongoing initiative at Cboe, so a solid command of containerization and orchestration concepts is expected even where recent hands-on time has been spent primarily in cloud-native services.
Direct, hands-on experience with agentic AI coding tools (e.g., Claude Code, GitHub Copilot, or similar) applied to real infrastructure or operations problems — not just general AI familiarity.
Experience designing or extending an agent framework or automation platform, including guardrails for safe autonomous action against production systems.
Hands-on experience with configuration management and network automation at scale (Ansible or equivalent), including configuration compliance and drift detection, and automated upgrade workflows with pre- and post-change validation.
Familiarity with global observability and monitoring platforms (e.g., Prometheus and Grafana) — enough to set direction, prioritize investment, and make sound architectural calls.
Working knowledge of network telemetry protocols and methods — SNMP, gNMI, syslog, and API-based polling — used to monitor the health of network and infrastructure devices at scale.
Working knowledge across network engineering, security engineering, and telemetry/observability — enough to credibly lead, hire for, and make technical decisions across all three domains.
Strong scripting and automation background (Python, Ansible, Terraform, or similar) and modern CI/CD and GitOps practices.
Excellent written and verbal communication skills, with the ability to translate technical concepts for both engineers and business stakeholders.
Candidates must be legally authorized to work in the United States without the need for employer sponsorship now or in the future.

Nice To Haves

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. To support strong partnership and team connection, this role follows a four day in office work model.

Responsibilities

Lead, mentor, and grow a multidisciplinary team of subject matter experts in network, security, and telemetry engineering, plus engineers focused on agent tooling and automation reliability. Own hiring, performance management, and career development for the automation function. Foster a culture of engineering excellence, disciplined execution, and agent-first thinking. Partner with peer Directors and VPs across Operations, Engineering, Security, and Network Engineering to align priorities and resourcing.
Own the systems that deliver automated configuration deployment across the network estate — Ansible today, and whatever proves better tomorrow — including source control, staged rollout, peer review, and reliable rollback. Build and maintain automations that continuously check device configuration against approved standards and baselines, surface drift, and progressively move the organization from detection toward automated enforcement. Deliver automated software and firmware upgrade tooling with rigorous pre- and post-change validation, so upgrades are repeatable, verifiable, and safe to run at scale. Build synthetic testing automations that routinely exercise critical infrastructure services and alert Operations the moment a service degrades or becomes unavailable.
Own the strategy for how network, security, and telemetry data flows into Cboe's global Prometheus and Grafana observability platform, and for the analytics and automation built on top of it. Ensure telemetry from SNMP, gNMI, syslog, and API-based polling is captured and correlated across the global network and infrastructure footprint. Set the standards for alerting on critical network events, covering thresholds, escalation paths, noise reduction, and on-call integration, in partnership with Network Engineering and Operations. Advance the use of machine learning and agentic analysis for anomaly detection, trend and capacity forecasting, and eventual auto-remediation.
Guide the technical direction of Cboe's existing agent framework, using agentic coding tools such as Claude Code to extend its capabilities. Establish engineering standards, guardrails, and review practices for agent-authored and agent-assisted changes to critical infrastructure. Stay hands-on enough to prototype, review, and unblock complex agent design and coding problems alongside the team. Champion responsible-AI practices, including human-in-the-loop controls, permissioning, and rollback safety, for autonomous agent actions. Drive advanced adoption of AI tooling across infrastructure teams, focusing first on network engineering and operations and expanding from there.
Define and own the multi-year strategic vision for using AI agents to enable Operations and Engineering to scale to 10x their current capacity. Build and present the business case, ROI models, and executive-level roadmap for continued investment in the agent platform. Serve as the primary point of contact for Operations and Engineering leadership seeking to leverage agentic automation, translating operational pain points into automation opportunities and measurable capacity gains. Prioritize a portfolio of automation initiatives across network, security, and telemetry domains, balancing strategic bets with near-term wins. Track and report on capacity and efficiency metrics that demonstrate measurable progress toward the 10x goal. Represent the automation program in senior leadership and cross-functional forums, and act as an internal evangelist for agentic engineering practices.
Partner with Information Security and Risk on governance frameworks for autonomous agents operating against production infrastructure. Ensure agent actions are logged, reviewable, and compliant with Cboe's change management and regulatory obligations. Own incident response and post-mortem processes for the automation platform.

Benefits

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
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