Top Tech Jobs & Startup Jobs in Chicago, IL

Lead AWS-based SRE activities for products migrated from on-prem: ensure reliability, observability, automation, CI/CD (GitOps), Kubernetes/EKS operations, Terraform IAC, database/RDS administration, networking and security, and collaborate with development and platform teams to optimize SaaS operations.

Oversee global endpoint management, including hardware standards, provisioning, imaging, software packaging, patching, OS updates, deployments, lifecycle management, and incident resolution. Manage vendors, budgets, reporting, KPIs, service agreements, root-cause analysis, and technical projects. Partner with users and department leaders to maintain reliable systems, communicate outages, improve processes, and provide training and support.

Coordinates client security questionnaires, due diligence requests, audits, evidence collection, and cybersecurity compliance responses. Manages SME input, deadlines, findings, remediation tracking, evidence repositories, reporting, and process improvements. Partners with Information Security, Technology, Legal, Product, and business teams while protecting sensitive information and supporting security frameworks, client obligations, and regulatory requirements.

Analyzes business and system requirements, translates them into functional designs, and supports technology enhancements and quality initiatives. Collaborates with stakeholders on project scope, timelines, testing, demos, and implementation. Monitors system usage, investigates errors and exceptions, assists with UAT, tracks project progress, communicates risks, and serves as a technology subject matter expert within the mortgage and secondary market domain.

Develops and implements AI-driven solutions by creating sophisticated prompts and agents, aligning initiatives with digital transformation strategy, and integrating AI into business workflows. Collaborates with technical and business teams to translate needs into AI use cases. Leads quality assurance, volume, bias, and ethical testing while ensuring scalability, reliability, compliance, and repeatable implementation across the organization.

Leads product strategy and delivery by representing customer and stakeholder needs, defining solution vision and roadmaps, prioritizing backlogs, managing epics and user stories, coordinating releases, and measuring outcomes. Partners with cross-functional delivery teams to ensure solutions are valuable, feasible, and aligned with organizational strategy. Conducts user research, manages dependencies and risks, communicates release information, and mentors team members.

Leads legal systems strategy and operations, owning Ironclad configuration, enterprise integrations, data flows, dashboards, analytics, AI enablement, procurement systems support, data governance, and legal technology initiatives. Partners with Legal leadership, cross-functional stakeholders, and technology teams to improve contract lifecycle processes, reporting, compliance, operational efficiency, and data quality.

Run hedge analyses and provide trading recommendations to institutional clients, primarily involving mortgage servicing rights. Develop and maintain valuation models and related data systems, explain methodologies across teams, oversee junior employees, and validate colleagues’ work for quality assurance. The role requires strong fixed-income modeling and trading knowledge, programming experience, leadership, and client communication skills.