Top Tech Jobs & Startup Jobs in Chicago, IL

Design, build, and maintain cloud infrastructure, CI/CD pipelines, and infrastructure-as-code. Ensure security, compliance, monitoring, logging, and auditability for federal systems. Automate developer workflows, mentor engineers, improve processes, and support continuous delivery while meeting federal data-protection and compliance requirements.

Design, build, and maintain end-to-end, accessible, secure full-stack software for a federal health/civilian agency. Build Section 508-compliant UIs, backend APIs, and services; follow API-first, CI/CD, automated testing, and security best practices; identify and remediate technical debt; mentor engineers and collaborate with cross-functional teams to deliver reliable, performant government software.

Lead Skylight's Defense & Security business with P&L accountability: grow federal defense, justice, and homeland security engagements, drive business development and proposals, build strategic relationships, assemble and manage multidisciplinary teams and subcontractors, ensure high-quality client delivery, oversee operations (people, finance), and translate market insights into service offerings while supporting hiring, mentoring, and occasional travel.

Lead and scale Skylight's growth by building strategies that leverage SBIR/STTR contract vehicles, coordinate business development, capture, proposals, account management, and marketing alignment. Drive adoption of AI/automation in growth workflows, support bids & proposals, and partner with executives to win federal professional services contracts.

Lead and scale company-wide people operations for a fast-growing digital consultancy. Oversee talent acquisition, HR compliance, HRIS management, compensation benchmarking, performance management, engagement, learning, succession planning, DEI initiatives, and partnership with business leaders. Manage recruiting leadership, onboarding/offboarding, and data-driven people programs while supporting government contracting requirements and occasional travel.

Lead a cross-functional team to define and deliver products that modernize government records migration, preservation, and access. Own product strategy, roadmap, prioritized backlog, stakeholder management, team ceremonies, and collaboration with government partners to transfer skills and align on scalable solutions.

Design, implement, and maintain cloud-native full-stack software to migrate, preserve, and make large volumes of government records searchable and accessible. Build Section 508-compliant frontends and secure backend APIs, follow API-first and CI/CD practices, defend against vulnerabilities, mentor engineers, and collaborate with cross-functional teams to deliver reliable, performant systems.