Top Tech Jobs & Startup Jobs in Chicago, IL

Responsible for leading the internal audit function, developing risk-based audit plans, ensuring financial and operational compliance, and providing strategic leadership to enhance risk management and governance processes.

Lead and expand Five9's data science team, focusing on AI products through research, experimentation, and data management. Direct technical methodologies while collaborating with stakeholders and enhancing customer experiences.

As VP of Engineering and AI Innovations, lead software development for AI products, enhance features, and manage product evolution in a team-first culture.

Operate and maintain IP networking in a 24/7 SaaS environment. Troubleshoot network issues, manage service providers and equipment, perform capacity planning, execute network changes, assist with network activations, and participate in projects to improve WAN/connectivity and integrate partners and acquisitions.

The Senior Mid-Market Account Director manages existing customer relationships and drives sales strategy, focusing on upselling and cross-selling Five9 products while exceeding sales targets.

Design, automate, deploy, and operate large-scale software-defined storage and Kubernetes platforms in a private cloud. Build IaC and GitOps workflows (Ansible, Terraform, Helm, Git), implement CI/CD for infra, manage backups, monitoring, and observability, troubleshoot cross-domain issues, participate in on-call/incident response, and produce runbooks and documentation.

Design, implement, and operate large-scale DNS and multi-tenant Kubernetes infrastructure in private cloud. Automate provisioning with IaC (Ansible, Terraform/Pulumi, Python), build CI/CD and GitOps pipelines, implement monitoring/alerting (Prometheus/Loki/Grafana), harden for HA and DR, perform deep troubleshooting across storage, hypervisors and networking, participate in on-call incident response, and collaborate on change management with global teams.

Operate and lead data-center LAN infrastructure in a 24/7 SaaS environment. Own troubleshooting, incident response, and change management across Cisco Nexus, Palo Alto, and F5 platforms. Drive projects, architecture (VXLAN/EVPN), automation (Ansible, Terraform, Python), observability (Prometheus, Grafana, SolarWinds), and cloud networking (AWS, GCP). Mentor junior engineers, participate in on-call rotation, and define operational standards, reliability metrics (SLI/SLO), and preventive engineering.

Lead modernization of internal platform tooling to 12-factor apps, delivering full-stack services (Go/Python + React/Vue), instrumenting observability (Grafana/Prometheus/Loki), driving Kubernetes-native GitOps (ArgoCD/GitLab CI), mentoring developers, and automating infrastructure with Ansible/Terraform on private/bare-metal clouds.

Architect, implement, and operate a multi-tenant OpenStack private cloud. Automate provisioning with Ansible/Terraform/Pulumi, extend core OpenStack services, build CI/CD update pipelines, implement monitoring/observability, harden for HA and DR, perform deep troubleshooting, and participate in on-call incident response and upstream contributions.