Director of Enterprise Applications

Preferred Risk Insurance•Chicago, IL

4d•$150,000 - $180,000

About The Position

The Director of Enterprise Applications is a strategic technology leader responsible for the vision, delivery, and ongoing performance of the enterprise business applications that run the company. This role owns the strategy, architecture, governance, and roadmap for core insurance systems, including policy administration, claims, billing, document management, integrations, and reporting, and leads the work to embed AI, automation, and modern cloud capabilities throughout the portfolio. The ideal candidate combines strong technical expertise with deep business process understanding within the insurance industry. This leader partners closely with executive leadership, operations, finance, underwriting, claims, compliance, and customer service teams to ensure enterprise systems drive operational excellence, scalability, regulatory compliance, and digital transformation. The Director will lead internal application teams, third-party vendors, and strategic technology initiatives while establishing governance, architecture standards, service delivery expectations, and a long-term enterprise applications roadmap aligned with business objectives.

Requirements

Bachelor's degree in information technology, Computer Science, Business Administration, or related field.
10+ years of progressive IT leadership experience.
5+ years leading enterprise applications teams in the insurance or financial services industry.
Experience managing large-scale enterprise business systems and integrations.
Proven experience leading enterprise application modernization, digital transformation initiatives and AI or intelligent automation initiatives.
Strong experience managing third-party vendors, system integrators, and SaaS providers.
Must be legally authorized to work in the United States for any employer without sponsorship
Reliable, punctual attendance is an essential function of the position

Nice To Haves

Experience in application development and managing multiple major project delivery of med-large scale projects/programs
Experience leading SaaS implementations and modernization of core business platforms, including policy, claims, or billing systems.
Experience with cloud platforms such as Azure or AWS, operating systems, databases and development languages
Knowledge of ITIL, COBIT, Agile, DevOps, and enterprise architecture frameworks.

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.
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.
Embed AI capabilities into core business systems where they create real value: underwriting assistants, claims automation and triage, intelligent document processing, conversational service, and across business functions.
Ensure system reliability, performance, scalability, and security across all application environments, including appropriate oversight and explainability for AI components.
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.
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.
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.
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.
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.