AI Transformation Director

Job DetailsLevel: ManagementJob Location: Skokie Home Office LSMSK - Skokie, IL 60077Salary Range: $120,000.00 - $140,000.00 Salary/yearSCOPE:

AI Transformation director: This role is focused on improving how work actually gets done across accounting, operations, maintenance, reporting, leasing, and administrative teams. The ideal candidate will work closely with department leaders and front-line staff to identify repetitive processes, operational bottlenecks, reporting gaps, and manual workflows, then implement practical AI and automation solutions that create measurable business value.

We are looking for someone who can both think strategically and execute operationally — someone comfortable mapping workflows, building automations, improving reporting, testing AI tools, and helping teams adopt new systems and processes.

The role will also help leadership prioritize larger AI and process-improvement initiatives and establish a long-term roadmap for responsible AI adoption across the company.

RESPONSIBILITIES:

Operational Workflow Improvement

Work directly with accounting, operations, maintenance, leasing, and administrative teams to understand current workflows and identify inefficiencies
Identify repetitive/manual tasks that can be improved through AI, automation, better reporting, or cleaner operational processes
Document current-state and future-state workflows across departments
Improve visibility into operational issues, follow-ups, exceptions, bottlenecks, and reporting gaps
Reduce spreadsheet-heavy and manual administrative processes

 AI & Automation Implementation

Build and deploy lightweight automations, AI workflows, dashboards, internal tools, and reporting systems
Implement AI-assisted processes for document handling, reporting, communication workflows, task tracking, and operational coordination
Work with tools such as ChatGPT, Claude, Microsoft Copilot, Zapier, Make, n8n, Power Automate, Airtable, APIs, Excel/Sheets, or similar platforms
Coordinate with software vendors, consultants, and internal teams on larger system integrations or automation initiatives
Evaluate emerging AI tools and recommend practical solutions appropriate for business operations

Data, Reporting & Decision Support

Improve operational and financial reporting visibility across departments
Create dashboards, alerts, reports, and tracking systems that help managers identify issues earlier and make faster decisions
Support cleaner data processes, better reporting consistency, and improved operational metrics
Help leadership prioritize AI and automation opportunities based on operational impact, feasibility, and ROI

Cross-Functional Collaboration & Change Management

Serve as a bridge between business operations and technical implementation
Work closely with department leaders to prioritize workflow improvement opportunities
Train employees on approved AI tools and best practices
Help establish practical AI governance, data privacy standards, permissions, and audit processes
Support organizational adoption of new tools, systems, and workflows through clear communication and documentation

QUALIFICATIONS:

3–8+ years of experience in operations, workflow automation, business systems, AI implementation, process improvement, analytics, or related roles
4yr degree in relevant field of process improvement and computer sciences
Strong understanding of operational workflows and business process improvement
Comfortable working directly with non-technical teams and learning how work is performed in day-to-day operations
Experience implementing AI tools, automation platforms, reporting systems, or workflow improvements in a business environment
Strong communication and organizational skills
Ability to manage multiple cross-functional initiatives simultaneously
Experience leading operational improvement or technology adoption initiatives preferred
Real estate, property management, accounting operations, field operations, or multi-location business experience strongly preferred

  Technical Skills Preferred

ChatGPT, Claude, Microsoft Copilot, or similar AI platforms
Workflow automation tools such as Zapier, Make, n8n, Power Automate, Airtable, or similar
Advanced Excel or Google Sheets experience
Dashboard and reporting tools such as Power BI, Tableau, Looker Studio, or similar
SQL, APIs, or basic scripting experience preferred
Familiarity with CRM, ERP, accounting, property management, or workflow systems
Experience working with operational reporting and business intelligence tools
Basic scripting or API experience preferred

FLSA CLASS: Exempt

REPORTS TO: CEO/CPEO

SUPERVIOSRY RESPONSIBILITIES: AI Implementation Operational

BUSINESS FUNCTION: Operations, Field

POSITION CLASS: Administrative

POSITION CODE: AITRADIR                               

COMPETENCIES:  

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