Top Tech Jobs & Startup Jobs in Chicago, IL

The Underwriting Associate will assist with underwriting insurance risks, ensuring compliance with various regulations, and providing support to underwriters and agents. Responsibilities include analyzing quotes, processing endorsements, collaborating with partners, and identifying risks requiring reinsurance.

Manage and analyze pay programs including salary structures, incentive and equity plans. Conduct market pricing, compensation analyses, compliance checks, vendor coordination, and support annual planning and compensation operations.

Lead and scale the enterprise virtual risk assessment program by translating strategy into operating plans, governance, quality controls, workforce plans, and technology adoption. Oversee day-to-day virtual operations, capacity planning, vendor management, analytics-driven performance reporting, and integration with field operations. Coach and develop staff, manage stakeholder relationships, ensure compliance with industry standards, and perform complex virtual and occasional onsite assessments to maintain technical credibility and continuous improvement.

Own product vision, roadmap, and backlog; prioritize features by business value; write user stories and break down epics; engage customers and stakeholders for feedback; collaborate with technical leads and Scrum Master to remove roadblocks and ensure team delivers value in an Agile environment.

Support design and oversight of IT control framework for SOX and internal audits. Test ITGCs/ITACs, lead process walkthroughs, create SOX documentation, conduct IT risk assessments, evaluate deficiencies and remediation, recommend automation, and liaise with internal and external auditors.

Provide legal counsel on assumed and ceded reinsurance matters, draft and negotiate treaties and collateral instruments, advise stakeholders on coverage and regulatory issues, support M&A and due diligence, develop policies and templates, monitor legal developments, build market relationships, and leverage legal technology and process improvements to enhance contracting and risk management.

Oversee reinsurance accounting operations, ensure compliance and accuracy, lead the team, drive process improvements, and collaborate with various departments.

Provide technical underwriting and administrative support for commercial P&C accounts within delegated authority. Analyze submissions, prepare quotes, endorsements, and renewals, document files, collaborate with internal partners, escalate recommendations beyond authority, engage agencies, identify upsell/reinsurance opportunities, and support portfolio reviews to meet KPIs and regulatory requirements.

Senior leader responsible for end-to-end management and improvement of the Alternative Distribution reinsurance business unit, including treaty administration, claims oversight, accounting/reporting, controls, regulatory compliance, process automation, data and systems integrity, budgeting, audit readiness, and cross-functional stakeholder management. Leads large transformation projects, manages DUA programs, and builds a high-performing team to optimize risk transfer, cost, and capital outcomes.