Top Tech Jobs & Startup Jobs in Chicago, IL

Handles first-party homeowner property claims from investigation through resolution. Responsibilities include assessing liability and damages, interpreting policies, making coverage and payment decisions, managing claim workloads, communicating with policyholders, agents, contractors, and vendors, reviewing estimates and engineering reports, documenting claim files, and resolving complex claims up to $100,000. The role is fully remote within eligible U.S. states, with some travel required.

Handles property and casualty claims coverage analysis for litigated and non-litigated matters. Reviews complaints and insurance contracts, determines defense and indemnification obligations, drafts reservation of rights and denial letters, develops legal strategies with counsel, evaluates complex injury demands, communicates coverage decisions, and monitors external defense attorneys for efficient litigation handling and cost containment. The role is fully remote within specified U.S. states, with occasional travel for meetings, training, mediations, conferences, or trials.

Lead the corporate accounting function, including monthly, quarterly, and annual close, GAAP financial reporting, reconciliations, audit and tax support, internal controls, compliance filings, vendor expenses, and accounting-system automation. Hire, mentor, and manage accounting staff while partnering with internal teams, external accounting firms, consultants, and vendors. Oversee accurate data integration across ADP, Concur, IMS, and NetSuite and report financial KPIs.

Lead planning, execution, and implementation of complex, cross-functional company initiatives. Coordinate internal teams, external vendors, systems, dependencies, resources, requirements, workflows, documentation, meetings, and project milestones. The role requires understanding insurance policy and claims lifecycles, technical system integrations, data flows, and business processes, while communicating proactively and removing blockers. This is a fully remote U.S.-based position with some travel for meetings and training.

Directs marketing strategy for P&C insurance products, including agent engagement, brand communications, content, campaigns, events, website strategy, CRM workflows, and marketing analytics. Leads HubSpot initiatives, measures campaign ROI, manages budgets, collaborates with sales and underwriting, and mentors a two-person marketing team. The role requires insurance-sector marketing experience, strong content and communication skills, and travel for conferences and industry events.

Execute manual test plans, perform ad-hoc testing, troubleshoot test and production issues, validate data using SQL, create targeted test cases from specs, interpret API documentation, test JSON/XML, and leverage AI tools to optimize manual testing for the company’s policy management system.