Top Tech Jobs & Startup Jobs in Chicago, IL

Provides consultative guidance on Medicare Secondary Payer compliance, Medicare Set-Asides, structured settlements, and complex workers’ compensation and liability claims. Leads client and internal discussions, supports account retention and growth, monitors regulatory developments, and develops educational and thought leadership content. Requires extensive claims experience, California workers’ compensation expertise, strong communication skills, and approximately 20% travel.

Independently manages complex Management Liability claims, including D&O, EPL, Fiduciary Liability, Crime, and financial lines matters. Responsibilities include coverage analysis, litigation and defense counsel management, reserves, settlements, portfolio reporting, broker and carrier relationships, underwriting partnership, mentoring, compliance, and claims process improvement.

Audits specific stop loss claims for MGU and carrier clients. Analyzes claim data, validates eligible expenses against policies and plan descriptions, applies deductibles, coinsurance, aggregating deductibles, and lasers, and follows up on pended claims. Provides customer service to MGU partners and TPAs while supporting process improvements. Requires claims experience, healthcare repricing knowledge, Excel proficiency, strong analytical skills, attention to detail, and effective communication.

Promotes and sells assigned insurance coverage through phone, email, mail, and fax. Prioritizes leads, presents quotes, closes sales, facilitates applications and underwriting, records activities in the CRM, and services clients during their first year of coverage. Builds customer relationships while meeting territory-based sales goals and gathering market intelligence.

Promote and renew insurance coverage for existing clients through phone, email, mail, and fax. Facilitate applications and underwriting, present quotes, close sales, sell ancillary products, document activities in the CRM, answer coverage questions, and maintain client relationships. The role requires an active Property and Casualty insurance license and involves supporting other account representatives as needed.

Own data quality across systems by designing validation rules, reconciliation processes, profiling workflows, and quality controls. Investigate discrepancies to identify root causes, apply statistical methods to detect anomalies, evaluate machine learning model outputs, and communicate findings to technical and non-technical stakeholders. Partner with engineering, BI, and business teams to establish data quality standards, metrics, controls, and reporting practices.

Manage captive and commercial property and casualty insurance accounts through new business, renewals, policy servicing, documentation, billing, compliance, and client communications. Analyze loss runs, coordinate with brokers, carriers, claims teams, and service providers, support sales and retention initiatives, draft policy documents, and maintain accurate Salesforce records. The role requires strong customer service, analytical, organizational, communication, and multitasking skills.

Analyze and model property catastrophe reinsurance treaties using catastrophe modeling platforms. Prepare and validate exposure data, execute models, interpret risk metrics, develop scenarios, and identify portfolio risk drivers. Support underwriting, actuarial pricing, placement, renewals, and management decisions through clear reporting. Participate in model validation, calibration, research, and development while collaborating with underwriters, actuaries, and other stakeholders.

Leads national financial analytics strategy for a pharmacy consulting practice, managing actuaries and analysts while overseeing PBM financial models, pricing analyses, forecasting methodologies, and proprietary analytics platforms. Advises leadership and clients on contracts, rebates, utilization, specialty drug trends, and total cost of care. Drives team development, process standardization, quality governance, product innovation, and thought leadership across pharmacy benefit financial analytics.

Manage accounting, financial reporting, regulatory filings, audits, budgets, and compliance for a portfolio of captive insurance companies. Serve as the primary accounting contact for clients, senior management, regulators, auditors, and service providers. Prepare GAAP, SAP, and modified GAAP financial statements; coordinate audits; explain financial results; and support process improvements across accounting systems. The role requires strong insurance accounting knowledge, client management, analytical skills, and the ability to manage multiple deadlines independently.