Top Tech Jobs & Startup Jobs in Chicago, IL

Lead client engagements applying generative AI to business workflows, especially in regulated mortgage environments. Responsibilities include scoping use cases, building prototypes and proofs of concept, facilitating discovery sessions and learning labs, developing prompts and reusable solution artifacts, creating enablement materials, advising stakeholders on AI adoption, and collaborating with compliance and technical teams to scale successful experiments.

Supports Department of Veterans Affairs technology modernization and legacy system decommissioning by conducting current-state analysis, stakeholder interviews, capability assessments, and data-flow analysis. Develops user stories, business rules, future-state processes, gap assessments, solution options, and client documentation. Contributes to product design and development while maintaining strong client and team relationships. Requires five years of relevant experience, analytical and communication skills, Microsoft Suite proficiency, and eligibility for Public Trust clearance.

Supports a federal IT modernization initiative by gathering and documenting requirements, mapping current- and future-state workflows, developing user stories and acceptance criteria, analyzing dependencies and risks, and coordinating with business, product, engineering, and data stakeholders. The role maintains traceability and documentation, supports change management and impact analysis, validates technology alignment, and communicates project status, risks, and issues to leadership.

Designs and integrates AI-enabled modernization solutions while establishing quality assurance frameworks for AI-generated code, skills, agents, and prototypes. Develops test plans, acceptance criteria, regression suites, automated testing, security scans, and quality gates. Collaborates with DevOps teams on reliable multi-agent workflows, validates prototypes for production readiness, and monitors accuracy, security, compliance, and data-sensitivity risks.

Creates and maintains requirements, solution design, operating model, and architecture documentation for technical programs. Translates complex technical decisions and diagrams into clear materials for technical and non-technical audiences. Updates architecture diagrams, manages documentation version control, ensures Section 508 accessibility, and collaborates with architects, DevSecOps, cybersecurity, database, federal client, and delivery teams. The role requires technical writing samples, diagram-based work samples, and eligibility for a Public Trust clearance.

Own product strategy and backlog modernization for the VA Loan Guaranty technology portfolio. Translate policy and stakeholder needs into prioritized roadmaps, precise user stories, acceptance criteria, and executable plans. Coordinate releases, UAT, analytics, legacy decommissioning, and configuration-versus-customization decisions across VA, lenders, servicers, architecture, and engineering. Apply AI tools to policy analysis, requirements drafting, and feedback synthesis while respecting federal security and privacy boundaries.

Lead DevSecOps and platform engineering for a federal modernization program spanning legacy and modern systems. Own CI/CD, zero-downtime releases, infrastructure as code, security automation, observability, reliability, disaster recovery, and legacy-to-modern transition efforts. Lead and mentor engineers while remaining hands-on with architecture, coding, incident response, and code review. Build AI-enabled engineering workflows within federal security boundaries and partner directly with customers to improve delivery speed, security, and operational performance.

Own enterprise and solution architecture for a federal home loan guaranty modernization. Define target-state architecture, solution designs, data models, integrations, migration and legacy decommissioning strategies across Salesforce, serverless government-cloud services, and legacy systems. Lead architecture reviews, enforce configuration-first standards, embed security and compliance, support mortgage data exchanges, advise federal customers, and mentor technical teams. Apply AI tools responsibly to analyze legacy systems and accelerate architecture documentation and design.

Lead multiple cross-functional engineering teams delivering monthly releases across Salesforce-centered modern platforms and legacy systems. Own delivery commitments, engineering standards, test automation, defect prevention, release quality, documentation, and federal compliance. Develop AI-native engineering practices, manage customer communication, flex team structures, and hire and grow technical leaders. The role requires maintaining zero escaped critical defects, high pre-UAT defect detection, rapid critical bug resolution, and stable modernization alongside legacy sustainment.

Architect AWS infrastructure and Infrastructure-as-Code solutions supporting a RHEL 7-to-RHEL 8 migration across GovCloud environments. Design AWS accounts, VPCs, EC2, RDS, secure integrations, reusable Terraform and CloudFormation templates, and CI/CD automation. Provide technical direction, lead architecture and design reviews, incorporate security scanning and compliance requirements, define migration validation strategies, and coordinate with federal stakeholders and delivery teams.