Top Insurance Jobs in Chicago, IL

Gather and document business requirements, collaborate with insurance carrier stakeholders, define scope decisions, and translate requirements into technical specifications for engineering implementation. Organize complex product configuration datasets and support data-driven solutions during a six-month implementation engagement.

Lead a team of software engineers building and scaling Spark’s broker productivity platform. Responsibilities include architecting full-stack solutions, guiding technical direction, reviewing code, managing infrastructure priorities, coordinating product planning, sequencing projects, coaching engineers, hiring, and ensuring reliable, high-quality delivery. The role balances hands-on engineering with people management and is fully remote within the United States.

Lead Atticus’s corporate communications and public relations function, building media presence, policy-driven storytelling, rapid response, public affairs, Congressional engagement, executive thought leadership, crisis preparedness, agency management, communications operations, and a growing team. Use proprietary data and client stories to shape coverage and policy conversations around Social Security, disability benefits, and access to legal help.

Leads the company’s information security operations and reports to the CISO. Oversees SIEM, threat detection, vulnerability management, penetration testing, incident response, SOC 2 Type II compliance, third-party risk, security awareness, cloud and endpoint security, and regulatory cybersecurity coordination. Manages security policies, breach readiness, tabletop exercises, KPIs, audits, and emerging technology evaluations while partnering with IT, infrastructure, compliance, regulators, and executive leadership.

Owns relationships, onboarding, implementation, renewals, retention, expansion, and revenue growth for health plan customers. Leads product rollouts, quarterly business reviews, ROI optimization, volume monitoring, executive relationship management, and cross-functional customer feedback. Requires B2B account management or customer success experience, healthcare payment integrity knowledge, SaaS implementation expertise, quota performance, and strong communication and project management skills.

Own and resolve complex medical billing and insurance cases end-to-end after AI handoff. Contact providers, insurers, and collections; investigate claims and benefits; advocate for users; maintain clear documentation; communicate progress; and improve playbooks while partnering with Product and Engineering.

Lead product analytics for a B2B SaaS product: define metrics and measurement frameworks, analyze user behavior and product performance, build self-service dashboards, partner cross-functionally to link usage to business outcomes, and translate data into strategic recommendations for product roadmap and GTM decisions.

Lead end-to-end enterprise sales for an AI-native claims platform: own complex deals, shape GTM playbook, influence product roadmap, represent Vega to senior insurers, and build repeatable sales processes and mentorship.

Leads financial operations accounting, including inventory balancing, journal entries, account reconciliations, cash and refund processing, manual clearing activities, and special operating checks. Supervises technical staff, oversees testing and training for system implementations, researches system issues, collaborates with IT, and manages employee development and work assignments.

Leads full-cycle recruiting for complex and high-impact positions, advises hiring managers, develops sourcing strategies, and provides talent market intelligence. Coaches recruiters, analyzes recruiting metrics, manages stakeholder relationships, and drives cross-functional process improvements. The role requires advanced talent acquisition expertise, recruiting technology proficiency, negotiation skills, and experience hiring for technical roles. It is hybrid, with three days in the office and two days remote, and does not offer sponsorship.

Own one of Jerry.ai’s emerging 0-to-1 product bets, such as home, motorcycle, boat, RV insurance, or property-tax services. Identify customer needs, analyze quantitative and qualitative data, prioritize high-impact opportunities, build and launch products, gather feedback, iterate, achieve product-market fit, and scale successful offerings. The role requires strong ownership, consumer product judgment, analytical thinking, and comfort navigating complex regulatory and operational challenges.

Work directly with the CEO on high-leverage business problems across product, growth, operations, finance, engineering, and data. The program provides broad exposure to Jerry’s rapidly expanding business lines, with the expectation that successful participants eventually own P&L for a business line. The role requires strong ownership, urgency, resilience, learning ability, and in-person collaboration in Palo Alto during the initial 6–12 months.

Develop product-building skills while working directly with the CEO to build or scale new product verticals. Responsibilities include identifying opportunities, executing growth strategies, navigating operational complexity, and collaborating across product, growth, operations, finance, engineering, and data. The role offers broad exposure to startup functions and may lead to future product or commercial leadership opportunities.