Top Tech Jobs & Startup Jobs in Chicago, IL

Leads a cross-functional team delivering an AI-enabled federal decision-support capability from discovery through deployment and operations. Owns technical strategy, architecture, integration, security, quality, delivery planning, risk resolution, and organizational development. The role aligns software, data, AI, infrastructure, cybersecurity, and product teams into a secure, explainable, maintainable system while partnering with customers and stakeholders. It is a remote-first role requiring occasional travel and US citizenship with Secret clearance eligibility.

Owns end-to-end administration of AWS, Azure, Microsoft 365, and Entra ID environments. Responsibilities include cloud infrastructure, networking, identity, endpoint management, Terraform-based infrastructure as code, automation, monitoring, security hardening, vulnerability remediation, compliance, AI platform administration, and audit-ready documentation. The role partners with engineering, security, and operations to deliver stable, secure, scalable, and well-documented services in a defense-sector compliance environment.

Lead software design, architecture, and delivery for a government program: own end-to-end build, integrate optimization/analytics, manage unclassified-to-secure transfer, coordinate PM/SMEs/data scientists, lead a small engineering team, and ensure deployments with CI/CD and security practices. Customer-facing role requiring hands-on coding and program accountability.

Own full-cycle technical and non-technical recruiting, with a primary focus on hiring specialized engineering talent for DoD and government-contracting programs. Develop cleared-talent pipelines, partner with hiring managers, negotiate offers, and improve candidate experience. Lead and scale onboarding and support People Operations process improvements, including employee lifecycle workflows, documentation, and data integrity. Serve as a strategic partner to the Head of HR in a fully remote, high-growth AI and defense technology company.

Own and operate contract and subcontract administration for a US defense program: draft, negotiate, maintain records, drive milestone and invoice readiness, design scalable contract processes, coordinate with leadership and finance, assess changes, and ensure contractual compliance and audit readiness.

Build and maintain data and model layers for an AI decision‑support system: data ingestion, probabilistic record matching, calibrated scoring, provenance‑tracked retrieval and grounded generation, and secure production pipelines. Ensure explainability, auditability, and accredited deployment in a controlled government cloud environment.