Director of Network Automation & Tooling

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 Team & Organizational Leadership 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 Network Automation, Telemetry & Intelligent Alerting 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 Agentic Coding & Framework Extension 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 Agentic Automation Strategy & Stakeholder Partnership 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 Governance, Security & Risk 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 Experience designing or extending an agent framework or automation platform, including guardrails for safe autonomous action against production systemsOriginal 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 themA 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. The following specifics are required: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 servicesStrong scripting and automation background (Python, Ansible, Terraform, or similar) and modern CI/CD and GitOps practicesWorking 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 scaleExcellent written and verbal communication skills, with the ability to translate technical concepts for both engineers and business stakeholdersHands‑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 infrastructureLeadership 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 anywayComfort 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 followsHands‑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 validationWorking knowledge across network engineering, security engineering, and telemetry/observability — enough to credibly lead, hire for, and make technical decisions across all three domainsFamiliarity with global observability and monitoring platforms (e.g., Prometheus and Grafana) — enough to set direction, prioritize investment, and make sound architectural callsDirect, 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 familiarityExecutive 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 shouldA track record of conceiving something that didn’t exist and then getting it built. Specifically: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 #J-18808-Ljbffr Cboe