Jobs · Information Technology · Illinois

Director of Enterprise Applications

Warrior Insurance Network · Chicago, IL · 2 wk ago
Information Technology$150k–$180k/yrFull-time

Key Responsibilities

  • Develop and execute the enterprise applications strategy that enables corporate growth, embeds AI capabilities into core insurance operations, and delivers measurable business outcomes.
  • Maintain a multi-year applications roadmap supporting AI adoption, scalability, operational efficiency, automation, analytics, and user experience improvements.
  • Partner with executive leadership and business stakeholders to prioritize technology investments using a capability, value, risk, adoption, and AI-leverage lens.
  • Serve as the strategic technology partner for capabilities supporting underwriting, claims, finance, customer service, distribution, and regulatory reporting.
  • Drive modernization initiatives, including cloud transformation, SaaS optimization, AI-enabled engineering practices, intelligent automation, and API-driven integration on reusable, scalable platforms.

Application Portfolio Management

  • Oversee the administration, support, enhancement, and optimization of enterprise business systems, including policy administration, claims, billing, document management, data integration, and reporting and analytics platforms.
  • Evaluate and rationalize application portfolio usage, licensing, vendor relationships, and total cost of ownership with attention to each platform's openness to APIs, data access, and AI extensibility.
  • Lead application upgrades, migrations, implementations, and decommissioning efforts.

Insurance Operations & Business Partnership

  • Collaborate with underwriting, actuarial, claims, compliance, finance, and operations leaders to improve business processes and system capabilities.
  • Identify and prioritize workflows where AI and intelligent automation can drive measurable improvement in cycle time, accuracy, customer experience, and cost.
  • Translate business needs into scalable technical solutions that support regulatory compliance and operational excellence.
  • Ensure systems and AI use support NAIC compliance, state regulatory requirements, audit standards, data retention policies, and cybersecurity mandates.
  • Support business continuity planning and disaster recovery initiatives for mission-critical platforms.

Technology Governance & Architecture

  • Establish governance processes for application development, change management, release management, testing, and production support progressively automated through CI/CD and observability.
  • Define enterprise application standards, integration strategies, and architectural principles that favor APIs, composability, and extensibility for AI.
  • Establish AI governance practices covering approved tools, model and vendor selection, data handling, human oversight, monitoring, and incident response.
  • Oversee vendor management, contract negotiations, SLA performance, and third-party application support relationships.
  • Partner with infrastructure, cybersecurity, data, and enterprise architecture teams to ensure cohesive technology solutions and compliance with IT controls, audit requirements, SOX (if applicable), and cybersecurity frameworks.

Leadership & Team Development

  • Lead, mentor, and develop a high-performing enterprise applications team, including managers, analysts, developers, architects, and support personnel.
  • Build AI fluency across the team so engineers, analysts, and leads use AI tools daily to deliver more and deliver faster.
  • Foster a culture of accountability, innovation, collaboration, and continuous improvement.
  • Manage staffing strategy, succession planning, performance management, and professional development, with hiring and development aligned to AI-augmented ways of working.
  • Build strong cross-functional relationships between IT and business stakeholders.

Project & Program Delivery

  • Lead complex enterprise technology initiatives from planning through implementation and stabilization.
  • Oversee project budgets, timelines, resource planning, and risk management activities.
  • Drive Agile and iterative delivery methodologies, applying AI tools across the SDLC to accelerate delivery.
  • Ensure successful user adoption through training, communication, and change management programs.
  • Measure and communicate project outcomes, operational KPIs, business value, and AI leverage.

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