Director of Enterprise Applications / Hybrid / South Suburbs of Chicago

A leading insurance organization based in the south suburbs of Chicago is seeking a full-time Director of Enterprise Applications to lead the strategy and delivery of its core business systems. This role will oversee a complex ecosystem including policy administration, claims, billing, integrations, and reporting platforms, with a strong focus on cloud technologies, AI-driven capabilities, and modern architecture practices.

They require you to go into the office Tues-Thurs. This is a high-impact leadership opportunity for someone who wants to shape the future of enterprise technology within a regulated, operationally complex environment. The organization is investing heavily in AI, automation, and digital transformation, and needs a leader who can bridge business strategy with technology execution. You'll influence enterprise-wide decisions, lead modernization initiatives, and build a forward-looking applications ecosystem that drives measurable business value. Required Skills & Experience 10+ years of IT leadership experience
5+ years leading enterprise applications teams in insurance or financial services
Experience managing policy, claims, or billing platforms
Strong background in enterprise systems integration and APIs
Proven experience with digital transformation and modernization initiatives
Experience with AI, automation, or advanced analytics initiatives
Vendor management and SaaS platform oversight Desired Skills & Experience Experience leading large-scale platform implementations or migrations
Knowledge of insurance regulatory environments (NAIC, compliance frameworks)
Familiarity with Azure, AWS, or cloud-native architectures
Background in Agile, DevOps, or CI/CD practices
Exposure to enterprise architecture frameworks or governance models What You Will Be Doing Tech Breakdown
40% Cloud & SaaS Platforms (Azure/AWS)
30% Enterprise Applications (Policy, Claims, Billing)
20% AI & Automation Tools
10% Integration & APIs
Daily Responsibilities
40% Leadership & Strategy
30% Project & Program Oversight
20% Cross-Functional Collaboration
10% Hands-On Technical Guidance The Offer Bonus eligible
You will receive the following benefits:
Medical, Dental, and Vision Insurance
Vacation Time
Stock Options

Applicants must be currently authorized to work in the US on a full-time basis now and in the future.