Top Tech Jobs & Startup Jobs in Chicago, IL

Consults with large motor carrier customers to evaluate risks, analyze loss trends, and recommend risk mitigation strategies. Partners with National Accounts teams to acquire and retain profitable accounts, advises insured management teams, develops safety initiatives, coaches customers, and delivers presentations. The role is fully remote in the Midwest but requires frequent travel of 70%–80% monthly.

Provide administrative and sales support to Account Representatives and insureds: respond to requests for information, services, quotes, permits/licensing, and perform general clerical duties. Full-time in-office role supporting a trucking-focused insurance agency.

Leads QA automation initiatives by developing and maintaining automated functional, regression, API, and integration test suites for Guidewire software and mobile applications. Improves CI/CD pipelines, performs root cause analysis, drives quality improvements, collaborates with developers and product owners, and mentors junior QA engineers.

Leads business process improvement and organizational transformation initiatives. Analyzes workflows, maps processes, identifies inefficiencies, applies Lean and Six Sigma methods, evaluates performance data, recommends automation solutions, and partners with cross-functional leaders to implement scalable improvements and drive change adoption.