Top Tech Jobs & Startup Jobs in Chicago, IL

Lead design, delivery, and execution of enterprise technology strategy; advise senior leaders, drive cross-organizational change, manage a team, and implement strategic initiatives to achieve long-term business goals.

Build and operate automated adversarial testing pipelines to continuously validate exploitability and remediation. Integrate adversarial testing into CI/CD and enterprise workflows, automate attack path validation, partner with exposure intelligence and response teams, and scale penetration testing coverage.

Identify and prioritize data-layer exposure across RDBMS, NoSQL, object storage, and data warehouses. Correlate signals into exploitability-focused exposure narratives, identify attack paths to data access, and provide remediation guidance. Partner with data platform teams to reduce permissions issues, stale entitlements, and misconfigurations while tracking closure outcomes.

Senior security consultant role driving adoption of secure-by-design and threat modeling across platforms. Lead threat modeling engagements, influence architecture, embed security into CI/CD and development lifecycles, mentor engineers, and collaborate with Product Security, Security Operations, and Architecture teams to improve detection, resilience, and platform security posture.

Provide senior commercial legal counsel for Allstate's non-insurance businesses: draft, structure, and negotiate complex technology, data, and service agreements; advise on privacy, AI, and related legal risks; develop templates and playbooks; collaborate with sales, compliance, and cross-functional teams; lead process improvements and mentor team members. Remote role with supervisory duties and periodic travel.

Lead hands-on administration and optimization of enterprise database platforms (SQL Server, MongoDB, MySQL/MariaDB, PostgreSQL). Manage installs, upgrades, HA/DR, performance tuning, security, automation, monitoring, and capacity planning. Drive incident resolution, cloud modernization efforts, and mentor teams on database best practices.

Designs, implements, and runs Java Spring Boot microservices and REST APIs; leads design, CI/CD, TDD, performance tuning, security, and cross-product collaboration. Coaches teams and owns product KPIs and production support.

The Senior AI Engineer will focus on building AI-driven pipelines, semantic technologies, and enterprise ontologies while mentoring and ensuring best practices in a hands-on role.

Design, build, and support cloud-native full stack or backend Java products using TDD, CI/CD, microservices and event-driven patterns. Collaborate with product teams, provide production support, implement monitoring and ensure secure, performant systems.

The P&C Actuary Senior Consultant II executes and manages reserving projects, utilizing statistical standards and methodologies to inform insurance business decisions and strategies, mentoring others along the way.