Top Tech Jobs & Startup Jobs in Chicago, IL

Leads enterprise strategy, corporate planning, and complex cross-functional initiatives supporting CEO and executive priorities. Conducts market, financial, operational, and competitive analysis; develops business cases and recommendations; manages project governance, milestones, stakeholders, and execution. Prepares executive and Board materials, supports decision-making, and coordinates alignment with international stakeholders. Requires strong strategic, analytical, project management, communication, and influencing skills in a fast-paced insurance environment.

Support Financial Lines underwriting by evaluating financial statements, credit reports, industry trends, and client risk profiles. Assist with new and renewal business, coverage terms, data analysis, and underwriting decisions while collaborating with claims, legal, and finance teams. Gain practical experience through mentorship, projects, and ongoing insurance industry learning.

Provides high-level administrative and operational support to executives by managing complex calendars, meetings, communications, travel, expenses, records, vendors, events, and special projects. The role coordinates priorities across Financial Lines and Cyber businesses, prepares executive and board materials, tracks follow-ups, handles sensitive information, and serves as a professional liaison for internal and external stakeholders.

Lead a team delivering actuarial statistical reporting, regulatory submissions, and analytics. Ensure compliance with bureau requirements, drive automated reporting and UAT for policy/claims systems (Guidewire, Solartis), partner with actuarial, technology, and vendors, and manage stakeholder/regulator interactions while mentoring staff and improving data governance and reporting processes.