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
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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
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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
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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
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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:
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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
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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
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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:
- Treats everyone with respect, compassion and kindness – Builds internal respect and loyalty with customers. Demonstrates concern for customers. Effectively responds to customer needs. This includes responding timely to requests, listening to others, and seeking to understand others when there are differences of opinion, finding ways to build on each other’s ideas. Acts with empathy and focus, while able to resolve problems.
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Demonstrate integrity, transparency and doing things the right way – Makes lemonade out of lemons. This includes following policies, demonstrating financial responsibility with Lakeshore assets, complying with state and federal law, and practicing safety. Conforms to the highest professional standard. Turns challenges into wins.
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Collaboration and team work – Involve key stakeholders in decision making. This includes developing and maintaining positive work relationships. Enhances the level of mutual cooperation. Actively participates in team-oriented objectives and activities. Focuses on team success, over individual.
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Solves problems and is transparent about outcomes – Champions new initiatives beyond the scope of the department. Seeks to improve in all aspects of work performance. Creates an environment of continuous improvement and innovation. Encourages people to maintain high standards of quality and thoroughness.
- Serves our employees and residents to improve their lives – This includes maintaining the property that creates curb appeal, a welcoming community environment, supports individual and family activities, creates a sense of neighborhood. At work, continually challenges self to grow and develop to be the best you can be at work.
LOCATION: Skokie Home Office - IL
COMPENSATION: $120,000-$140,000.00/Year (Based on experience)
Physical Requirements and work environment:
While performing the duties of this job; the noise level in the work environment is usually moderate; Continually required to sit; Occasionally required to lift up to 10 pounds
Lakeshore embraces Diversity and Inclusion, and is an equal opportunity employer. Qualified applicants will receive consideration without regard to age, race, color, religion, sex, gender identity, sexual orientation, disability, national origin, or protected veteran status. Applicants are encouraged to confidentially self-identify when applying. Employment is contingent upon successful completion of background investigation including pre-employment drug screening. Lakeshore is a smoke-free and drug-free workplace, for the purpose of workplace safety. No recruiters or agencies without a previously signed contract. Only candidates whose profiles closely match requirements will be contacted during this search.
Job ID: 41010
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