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, delivery planning, risk management, security, quality, and operational readiness. Aligns software, data, AI, infrastructure, DevSecOps, and cybersecurity teams while partnering with customers and stakeholders. Builds and mentors the technical organization, resolves ambiguity, and ensures secure, explainable, maintainable systems are delivered effectively.

Administer AWS, Azure, Microsoft 365, and Entra ID environments end to end. Manage cloud infrastructure, networking, virtual machines, identity, endpoints, automation, Terraform-based infrastructure, monitoring, security hardening, vulnerability remediation, compliance evidence, and AI platform administration. Build resilient and governed environments, automate operational workflows, maintain documentation, support incident response, and partner with engineering, security, and operations. The role requires US citizenship and work within the United States.

Lead software design, architecture, and delivery for a defense-focused program: gather requirements, drive technical vision, coordinate cross-functional teams, implement front-end data-visualization features, integrate analytics/optimization, and manage unclassified-to-secure deployment and CI/CD to deliver working, government-deployable software.

Own full-cycle technical and non-technical recruiting, with a primary focus on hiring cleared or clearance-eligible talent for DoD and government contracts. Partner with hiring managers and senior leadership, build AI and defense talent pipelines, improve candidate experience, and lead onboarding. The role also supports People Operations by scaling onboarding, optimizing employee lifecycle processes, and advising the Head of HR on program design.

Own and operate contract and subcontract lifecycle for a major U.S. defense program: draft, negotiate, administer subcontracts, track milestones and invoice readiness, build scalable contract operations, maintain audit-ready records, support leadership with change-impact analysis and dispute resolution, and ensure contractual compliance across multi-party subcontractor ecosystems.

Lead and execute product design across Red Cell and its portfolio companies, creating high-quality user experiences and scalable design systems. Collaborate with teams to transition ambiguous problems into actionable design solutions and support marketing efforts.

Design and build data and model layers for an accredited AI decision-support system: record matching, calibrated scoring, provenance-tracked retrieval and generation, secure ingestion pipelines, model packaging/serving, and instrumentation for audit and accreditation.