Top Tech Jobs & Startup Jobs in Chicago, IL

Designs AWS-based technical solutions for federal and state government proposals and implements them in AWS environments. Leads technical proposal volumes, interprets solicitations, develops architectures, writes and reviews technical content, creates estimates, and coordinates technical teams. Designs AWS platforms, shared services, databases, networks, and Linux-based systems while evaluating technology options, documenting requirements, and supporting cloud implementations. Requires extensive AWS architecture, federal contracting, RFP solutioning, technical writing, and proposal experience.

Owns change control, release management, requirements traceability, deliverables, and ancillary organizational change management for a Medicaid Enterprise System program. Responsibilities include managing change requests, RTM traceability, release calendars, multi-vendor coordination, cutover and rollback planning, ITSM processes, decommissioning, certification evidence, stakeholder readiness, and reporting. The role is remote with periodic Raleigh travel and requires after-hours availability during deployments.

Owns the end-to-end training function for a Medicaid provider data management and credentialing solution. Responsibilities include developing training plans, role-based curricula, user documentation, guides, e-learning, training environments, train-the-trainer programs, evaluations, and accessibility-compliant materials. The role coordinates with business, change management, testing, and development teams; delivers training to State, vendor, provider, call center, and credentialing audiences; and supports UAT, releases, cutover, go-live, and ongoing operations.

Manages the full proposal lifecycle for Federal, State, and Commercial solicitations. Responsibilities include analyzing RFPs and RFQs, developing compliance matrices and schedules, coordinating cross-functional contributors, leading proposal reviews, ensuring compliance with evaluation criteria, overseeing editing and production, monitoring milestones, escalating risks, and improving proposal processes and tools.

Manages the NC Medicaid PDM/CVO contract as the accountable point of contact, overseeing compliance, SLAs, deliverables, invoicing, amendments, staffing, subcontractors, audits, disputes, reporting, and turnover. The role coordinates contractual obligations across implementation, certification, and operations while ensuring adherence to Medicaid, procurement, privacy, security, and state contracting requirements.

Designs, develops, deploys, and supports enterprise security automations, custom tools, integrations, and workflows. Responsibilities include Python-based application and API development, vulnerability enrichment, incident response automation, IAM administration, Linux and Docker platform support, and administration of SIEM, SOAR, endpoint, cloud, network, and other security technologies. The role also troubleshoots integrations, monitors operational health, supports security teams, and maintains resilient, secure configurations across enterprise systems.