IT Director

Camping World Holdings, Inc.•Lincolnshire, IL

3d•$179,000 - $274,400•Hybrid

About The Position

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.

Requirements

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 DevOps methodologies.
Excellent leadership, communication, and interpersonal skills.
Strong problem-solving skills and attention to detail.
Deeply fluent in applied AI, not just generally aware of it.
Hands-on familiarity with large language models, AI coding assistants, and agentic development tools.
Ability to evaluate, select, and integrate AI platforms into existing application architectures.
Technical depth to guide teams on prompt design, model selection, and AI-assisted testing and code review.
Judgment to set guardrails around AI-generated work, covering data privacy, security, intellectual property, and regulatory compliance.
Ability to know when human review must gate AI output before it reaches production or customers.
Ability to continuously reassess and upskill the team as AI tools and best practices evolve.
Ability to balance the speed AI enables with the reliability, quality, and accountability the business demands.

Nice To Haves

Master's degree
Certifications such as CISSP, ITIL, SAFe Agile, PMP are a plus.

Responsibilities

Develop and execute a comprehensive application strategy aligned with the Good Sam business goals and digital transformation initiatives.
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.
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.
Lead the planning, development, and execution of application-related projects, ensuring timely delivery and within budget.
Lead, mentor, and manage the IT teams, fostering a culture of collaboration, innovation, and continuous learning.
Provide technical guidance and mentorship to development teams, assisting with complex problem-solving and decision-making.
Monitor the performance of applications and ensure they meet user requirements, availability, and performance standards.
Implement processes to continuously assess and improve application performance.
Ensure that all application systems adhere to organizational standards, security protocols, and industry regulations (e.g., PCI, SOX, CCPA & CPRA etc.).
Evaluate and manage relationships with IT vendors and service providers to ensure cost-effective solutions and timely support.
Develop and manage the IT budget, monitoring expenses and identifying opportunities for cost savings and optimization.
Stay current with emerging technologies and industry trends, evaluating their potential impact on the dealership and recommending innovative solutions.
Provide training and development opportunities for IT staff to enhance their skills and knowledge, keeping them abreast of technological advancements.
Deeply fluent in applied AI, including hands-on familiarity with large language models, AI coding assistants, and agentic development tools.
Evaluate, select, and integrate AI platforms into existing application architectures.
Guide teams on prompt design, model selection, and AI-assisted testing and code review.
Set guardrails around AI-generated work, covering data privacy, security, intellectual property, and regulatory compliance.
Determine when human review must gate AI output before it reaches production or customers.
Continuously reassess and upskill the team as AI tools and best practices evolve.
Balance the speed AI enables with the reliability, quality, and accountability the business demands.

Benefits

Paid Time Off
401(k)
Employee Assistance Program
Good Sam Roadside Assistance
discounts
paid parental leave (if eligibility is met)
Tuition Reimbursement (if eligibility is met)
on the job training opportunities
comprehensive benefit package including medical, dental, vision and more! (Full-time associates)
access to dental & vision coverage (Part-time associates)