IT Director

We are seeking an experienced IT Director to lead the development, implementation, and management of our Good Sam organization's application systems. This role is responsible for overseeing a diverse portfolio of applications, ensuring they meet business needs, are cost-effective, and are scalable for future growth. The IT Director will collaborate closely with business leaders, technology teams, and external partners to drive digital transformation initiatives and ensure the delivery of high-quality software solutions.

This role is hybrid out of our Lincolnshire, IL offices and up to 25% travel is required to our Chicago, IL and Englewood, CO offices.

• Strategic Planning:
  Develop and execute a comprehensive application strategy aligned with the Good Sam business goals and digital transformation initiatives.
• Application Portfolio Management:
  Manage the selection, deployment, integration and ongoing support of software applications, including subscription management, membership and rewards, emergency and financial protection, CRM and other business-critical applications.
• Collaboration with Business Stakeholders:
  Act as a liaison between IT and business units, understanding their needs and ensuring that application solutions align with organizational goals. Partner with key business leaders to drive process improvements and automate workflows using appropriate application systems. Ensure effective training, user adoption, and support for business units using enterprise applications.
• Project Management:
  Lead the planning, development, and execution of application-related projects, ensuring timely delivery and within budget.
• Team Leadership:
  Lead, mentor, and manage the IT teams, fostering a culture of collaboration, innovation, and continuous learning.
• Technical Leadership:
  Provide technical guidance and mentorship to development teams, assisting with complex problem-solving and decision-making
• Systems Performance Management:
  Monitor the performance of applications and ensure they meet user requirements, availability, and performance standards. Implement processes to continuously assess and improve application performance.
• Governance and Compliance:
  Ensure that all application systems adhere to organizational standards, security protocols, and industry regulations (e.g., PCI, SOX, CCPA & CPRA etc.).
• Vendor Management:
  Evaluate and manage relationships with IT vendors and service providers to ensure cost-effective solutions and timely support.
• Budgeting and Cost Control:
  Develop and manage the IT budget, monitoring expenses and identifying opportunities for cost savings and optimization.
• Technology Evaluation:
  Stay current with emerging technologies and industry trends, evaluating their potential impact on the dealership and recommending innovative solutions.
• Training and Development:
  Provide training and development opportunities for IT staff to enhance their skills and knowledge, keeping them abreast of technological advancements.

• Bachelor’s degree in computer science, Information Technology, or a related field; master’s degree preferred.
• Proven experience (15+ years) in IT leadership roles, preferably in the automotive or insurance industry.
• A proactive and strategic thinker, able to drive change and innovate in a fast-paced environment
• Expertise in application development, deployment, and maintenance lifecycle
• In-depth knowledge of application integration, cloud platforms, and modern application architectures (e.g., microservices, APIs).
• Experience with Agile and Dev Ops methodologies
• Excellent leadership, communication, and interpersonal skills.
• Strong problem-solving skills and attention to detail.
• Certifications such as CISSP, ITIL, SAFe Agile, PMP are a plus.
• AI Fluency & Leadership:
  Because this delivery team relies on AI for roughly 90% of its work, the IT Director must be deeply fluent in applied AI, not just generally aware of it. This includes hands-on familiarity with large language models, AI coding assistants, and agentic development tools; the ability to evaluate, select, and integrate AI platforms into existing application architectures; and…