Top Insurance Jobs in Chicago, IL

The posting provides company background, benefits, interview recording and text messaging notices, but does not specify finance responsibilities or qualifications.

Leads Vantage’s highest-priority cross-functional enterprise initiatives from strategy through execution and scaling. The role develops project roadmaps, coordinates matrixed teams, manages risks and organizational change, establishes iterative delivery practices, tracks KPIs, and communicates progress and outcomes to executives and board stakeholders. Success requires strong influence without authority, operational rigor, strategic communication, financial acumen, and experience managing complex initiatives in distributed environments, preferably within insurance or financial services.

Directs lender due diligence engagements, assessing asset-based lending collateral and liquidation risk through transaction testing and borrowing base calculations. Leads collateral reviews for financial institutions, manages multiple projects, reviews and mentors junior staff, communicates with clients, prepares financial reports, supports business development, and identifies cross-selling opportunities. The role requires finance or accounting expertise, leadership, strong communication, attention to detail, and moderate travel.

Leads sales operations across enterprise accounts and consulting teams by managing account plans, opportunity stages, pipeline reviews, forecasts, proposals, RFPs, reporting, and stakeholder coordination. Maintains accurate sales information, assigns ownership, tracks timelines and capacity, identifies risks, and supports process improvements. The role requires strong commercial judgment, analytical and organizational skills, project management expertise, and the ability to influence senior stakeholders across sales, consulting, product, technology, and leadership teams.

Leads enterprise data transformation and integration strategy, overseeing data pipelines, governance, quality, security, compliance, and workflow optimization. Partners with business, governance, and IT teams to deliver scalable data solutions, manage vendors, and support regulatory requirements. Provides leadership and mentorship to data engineers and integration specialists while driving continuous improvement across data management practices.

Own the end-to-end lifecycle marketing and customer communications strategy across email, SMS, in-app messaging, and call scripting. Lead segmentation, personalization, experimentation, AI-enabled engagement, and product go-to-market launches. Partner with Product, Marketing, Sales, Operations, Analytics, Data Science, Legal, and Compliance to improve conversion and retention. Manage lifecycle platforms, vendors, governance, deliverability, messaging, and customer insights while ensuring compliant, measurable execution.

Supports commercial insurance policy placement through application and submission preparation, carrier follow-up, document collection, quote compilation, proposal assistance, renewal administration, and policy record maintenance. Coordinates with sales, service teams, carriers, and clients while ensuring accurate documentation, regulatory compliance, and timely communication. Uses AMS, ImageRight, Microsoft Office, and emerging AI solutions to support efficient client service.

Designs, builds, automates, and supports secure AWS cloud-native solutions. Responsibilities include Infrastructure as Code, CI/CD, serverless and containerized applications, APIs, integrations, databases, observability, authentication, AWS account provisioning, and troubleshooting across application and infrastructure layers. The role collaborates with architecture, security, application development, integration, and release engineering teams while developing reusable deployment patterns and automation.

Lead the launch and growth of Shepherd’s wholesale E&S insurance business and brand. Define products, underwriting appetite, broker distribution strategy, capacity partnerships, and financial targets. Hire and manage underwriting and distribution teams, establish authority and audit frameworks, collaborate on technology-enabled workflows, and own premium, profit, loss-ratio, retention, and expense results. Build broker and reinsurer relationships while coordinating with claims, actuarial, finance, product, engineering, and data teams.

Leads general liability underwriting, portfolio profitability, pricing, risk assessment, regulatory compliance, business planning, client development, and team management. The role underwrites new and renewal accounts, reviews exposures, collaborates with actuarial, claims, legal, and loss control teams, prepares financial and operational reports, develops business opportunities, and supports budgeting, staffing, process improvement, and acquisition integration.

Manages financial operations for a property and casualty insurance organization, including technical accounting, credit control, disbursements, bordereau processing, cash application, receivables, claims funding, and delegated authority operations. Leads teams, strengthens financial controls, resolves billing and collection discrepancies, supports reporting and process optimization, and partners with finance, legal, underwriting, claims, and operations stakeholders on strategic projects and system improvements.

The job description does not provide responsibilities, qualifications, salary information, travel expectations, or other role-specific details. It includes only the Vice President GL title and the employer’s equal opportunity and accommodation statements.