Top Tech Jobs & Startup Jobs in Chicago, IL

Lead research and integration of AI agent capabilities into cybersecurity workflows; design RAG pipelines and experiments; mentor clients and teams; run blue-team exercises; build detection rules, dashboards, and security tool tuning; analyze telemetry and perform threat hunting, incident response, and digital forensics; support customer assessments with up to 25–30% travel.

As a Cyber Range Engineer, design and manage computer networks, configure security tools, and troubleshoot IT systems while collaborating with clients and teams.

Contract Hiring Partner to manage full lifecycle recruiting across technical and nontechnical functions. Source active and passive candidates, build talent pipelines, maintain recruiting operations and data, support onboarding, and partner with hiring managers to improve processes and candidate experience over a six-month remote engagement.

Lead and grow a Core UI team owning the design system, shared component libraries, frontend architecture, and engineering-UX partnership. Drive standards for accessibility, performance, testing, and documentation; set roadmap and delivery priorities; mentor engineers; and collaborate with product, design, and other engineering teams to improve UI consistency and velocity.

As a Senior Sales Executive (Federal) at SimSpace, you will drive new business development across U.S. Federal agencies, focusing on cybersecurity and AI technologies, building pipeline, and closing complex sales deals.

Manage technical delivery of cyber range engagements: coordinate environments, lead exercise planning and execution, support AI agent training/validation, liaise between customers and Professional Services, document outcomes, and maintain customer relationships. Travel up to 25%.

Lead design, development, and operation of containerized microservices for offensive cybersecurity and user emulation. Drive architecture, mentor engineers, own end-to-end projects, define best practices, ensure reliability and security, collaborate cross-functionally, and implement monitoring, testing, and deployment pipelines for high-fidelity cyber range services.

Lead technical strategy and architecture for SimSpace's infrastructure, evolving CI/CD and multi-cluster Kubernetes platforms using Jsonnet and Grafana Tanka. Define SLIs/SLOs, build observability with the Grafana stack, embed security and compliance into pipelines, enable self-service developer tooling, command major incidents, and mentor engineering teams to improve reliability and scalability across cloud, on-prem, VMware, and air-gapped deployments.

The Senior Manager of Product Marketing will operationalize SimSpace's messaging, partner closely with Product and Sales, and create impactful materials for demand generation in the cybersecurity domain.

The Staff Site Reliability Engineer will lead the architecture and security of the SimSpace cyber range platform, focusing on reliability, automation, and observability across diverse deployment environments while mentoring engineers and driving infrastructure initiatives.