Job Description
Title: Director of Information Technology (AI-Driven Transformation)
Location: Chicago, IL - Onsite no remote
Salary Range: $160,000 – $180,000 + Bonus
Benefits: Health, Dental, 401K and additional benefits
Sponsorship:Position is not eligible for sponsorship
About the Opportunity
A growing organization seeking a hands-on Director of IT to lead and modernize its technology function. This is a high-impact, highly visible role where you will partner directly with business leaders to solve operational challenges through technology and AI.
This is not a traditional IT leadership role. The company is looking for a builder and problem solver who can move fast, leverage modern AI tools, and deliver real business outcomes.
What You’ll Do
- Act as the face of IT across the organization, partnering with business leaders to solve problems
- Build and deploy AI-driven solutions to improve operations, training, and workflows
- Rapidly create tools (e.g., training systems, internal apps, automation) that drive efficiency
- Own cybersecurity, audits, compliance, and overall IT risk posture
- Oversee infrastructure, networks, and enterprise systems across multiple locations
- Manage vendors, contracts, and technology spend
- Lead a small internal team while leveraging contractors for execution
What We’re Looking For
- 7+ years of IT leadership experience in a fast-paced environment
- Strong business acumen — able to translate needs into technical solutions
- Hands-on experience using AI tools (Claude or Grok strongly preferred) to drive productivity
- Experience across infrastructure, security, and enterprise systems
- Proven ability to build and ship solutions quickly
- Excellent communication skills with both technical and non-technical stakeholders
Why This Role
- High visibility and direct impact on business performance
- Opportunity to define and lead AI adoption across the company
- Blend of strategy + hands-on execution
- Fast-moving environment where you can actually build, not just manage
| Addison Group is an Equal Opportunity Employer. Addison Group provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, sexual orientation, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran in accordance with applicable federal, state and local laws. Addison Group complies with applicable state and local laws governing non-discrimination in employment in every location in which the company has facilities. Reasonable accommodation is available for qualified individuals with disabilities, upon request. |
IND 005-009
Numbers & Facts
| Location | Chicago, Illinois |
| Industry | Staffing/Employment Agencies |
| Salary | $160,000–$180,000 Per Year |
| Company Size | 1,500 to 1,999 employees |
| Year Founded | 1999 |
| Website | http://www.addisongroup.com/ |
About Company
Need a job? Need an employee? Then you need Addison Group, the professional staffing and search firm that has reshaped the industry with our excellent placements in the Administrative & HR, Engineering, Executive Search, Finance & Accounting, Healthcare, and IT sectors.
Addison Group has enjoyed rapid growth since its inception in 1999, when a group of visionary industry leaders in Chicago set out with the simple goal of recruiting the best candidates for the best companies. With the help of its strategic investment partner, Trilantic Capital Partners, Addison Group has expanded its reach across the country through 13 offices and six core industry sectors, from Administrative to IT.
Addison Group has enjoyed rapid growth since its inception in 1999, when a group of visionary industry leaders in Chicago set out with the simple goal of recruiting the best candidates for the best companies. With the help of its strategic investment partner, Trilantic Capital Partners, Addison Group has expanded its reach across the country through 13 offices and six core industry sectors, from Administrative to IT.
Skills
- Artificial Intelligence (AI)unmatched
- Automationunmatched
- Business Skillsunmatched
- Communication Skillsunmatched
- Contract Managementunmatched
- Distribution Servicesunmatched
- Enterprise Protectionunmatched
- Internet Securityunmatched
- Leadershipunmatched
- Network Monitoringunmatched
- Operational Improvementunmatched
- Problem Solving Skillsunmatched
- Process Improvementunmatched
- Retailunmatched
- Riskunmatched
- Technical Leadershipunmatched
- Vendor/Supplier Managementunmatched
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