Top Tech Jobs & Startup Jobs in Chicago, IL

Own day-to-day accounting operations, including premium accounts receivable, accounts payable, expense management, vendor administration, reconciliations, payments, reporting, audits, tax filings, and statutory reporting support. Prepare bordereau and carrier reporting, manage claims payments, and coordinate with brokers, carriers, auditors, banks, and tax agencies. Build AI-powered agents to automate accounting workflows and improve financial data processes. Report to the Controller in a fully remote insurance technology company.

Lead end-to-end insurance product launches, translating strategy into specifications and coordinating engineering, data, underwriting, and pricing priorities. Build scalable systems for expert rules, terminology, feedback, change control, testing, and shared infrastructure. Identify and eliminate operational bottlenecks, automate work with AI agents, and ensure cross-functional teams execute efficiently in a fast-moving environment.

Leads Counterpart’s engineering organization, technical vision, AI-native development strategy, infrastructure, engineering operations, and people strategy. Oversees resource allocation, engineering standards, delivery quality, reliability, observability, security, and regulatory compliance. Partners with executive leadership, product, investors, and the board while managing hiring, performance, compensation, and talent development across a distributed engineering team.

As a Production Risk Engineer, you will analyze risks, collaborate with teams, engage with brokers, and enhance insurance products while achieving performance goals.

Lead revenue operations to optimize revenue streams, build predictive dashboards, design quota and compensation, implement AI-driven workflows and automations, and align GTM teams through process, staffing, and enablement to hit topline targets.

The Account Executive will manage submission processing, support broker relationships, follow up on open quotes, and contribute to production goals while learning ML/PL products.

Own product problems end-to-end: gather requirements, build full‑stack features using AI, verify production quality, monitor and support services, and iterate to improve outcomes.

As a Claims Manager, you will manage claims investigations, collaborate with teams, analyze claims data, and ensure efficient resolution while maintaining relationships with stakeholders.