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AI Transformation Director

Job in Skokie, Cook County, Illinois, 60077, USA
Listing for: Lakeshore Management
Full Time position
Listed on 2026-05-24
Job specializations:
  • IT/Tech
    Business Systems/ Tech Analyst, Data Analyst, Data Science Manager
Salary/Wage Range or Industry Benchmark: 120000 - 140000 USD Yearly USD 120000.00 140000.00 YEAR
Job Description & How to Apply Below
SCOPE:

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 ROICross-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 roles4yr 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…
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