Top Tech Jobs & Startup Jobs in Chicago, IL

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 product direction for U.S. Air Force modernization and digital transformation efforts. Own product strategy, roadmaps, backlogs, requirements, prioritization, and release planning while guiding cross-functional teams of researchers, designers, engineers, and subject matter experts. Build trust with government stakeholders and vendors, manage changing priorities, and coach government partners on agile and customer-centered product practices. The role is fully remote, requires U.S. citizenship and a CAC background check, and includes quarterly travel to Air Force bases.

Leads end-to-end product design for U.S. Air Force modernization initiatives. Defines interaction flows, information architecture, and visual systems; conducts user research; creates interfaces in Figma; collaborates with product, engineering, research, and government stakeholders; shapes product strategy; and coaches partners on human-centered design during agile transformation.

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.

Own product direction for a U.S. Air Force legacy modernization effort. Lead cross-functional teams, develop product strategy and roadmaps, prioritize backlogs, write user stories, manage architecture and integration tradeoffs, and deliver iterative releases. Partner closely with government stakeholders, transfer product and digital skills, navigate organizational change, and apply lean, agile, and human-centered design practices. The role is fully remote with occasional quarterly travel to Air Force bases and requires U.S. citizenship and the ability to obtain a Common Access Card.

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.