AI Enablement Specialist

Job Location:

Corporate Headquarters - CHICAGO, IL, Salary Range: $65000.00 - $75000.00

Position Title:

AI Enablement Specialist

Department:
Sales

FLSA Status:
Non-Exempt

Location:

Hybrid (In office 3 days per week)

Reports to:

Chief Sales Officer

Effective Date:
October 2026

Choose Chicago is the official sales and marketing organization for our city, promoting Chicago as a global visitor destination to business and leisure travelers.

Choose Chicago is seeking a highly motivated, innovative, and adaptable professional to serve as the organization’s AI Enablement Specialist. This newly created role represents an exciting opportunity to help shape the future of one of the nation’s leading destination marketing organizations as artificial intelligence and emerging technologies become increasingly integrated into daily business operations and long-term strategy.

This role is approximately 70% dedicated to serving as the organization's primary internal liaison to Choose Chicago's external AI consultancy, coordinating implementation of system automation and technology initiatives and helping build a culture that fully embraces the adoption of AI and innovation across the organization including Sales, Marketing, Communications, Client Services, Human Resources, Finance, and Operations.

The remaining 30% provides executive-level administrative support to the Chief Sales Officer, Vice Presidents of Sales, and Vice President of Client Services (collectively, “Sales and Client Services leadership”); these Sales Executives will rely on the Specialist to help manage communications and relationships with Choose Chicago leadership, clients, partners, and staff.

The ideal candidate will be experienced in handling a wide range of project management and executive support related tasks and must have a high level of interpersonal skills to handle sensitive and confidential situations. The candidate must be exceedingly well organized, flexible, and able to work in a fast-paced environment while maintaining an overall awareness of the Sales Executives’ business activities.

As the organization matures in its AI adoption, the Specialist will also look for opportunities to streamline these support functions using AI and automation tools where appropriate, reflecting the role's broader charge to model AI adoption within the department. Reporting directly to the Chief Sales Officer, this role offers regular exposure to executive leadership and department heads during a period of organizational modernization.

• Serve as Choose Chicago's primary internal point of contact for the organization's external AI and technology consultancy.
• Coordinate communication, implementation timelines, project follow-up, and cross-departmental collaboration related to AI and automation initiatives.
• Support the rollout of customized AI solutions and technology tools, working with departments to identify opportunities for operational improvement, automation, and workflow efficiency.
• Assist in developing and documentation of processes and best practices for AI implementation and technology adoption.
• Help build and foster a culture that fully embraces the adoption of AI and innovation across the organization.
• Monitor emerging AI and technology trends relevant to destination marketing, hospitality, and tourism operations.
• Support staff training and onboarding on new technology systems and AI tools and develop internal communications and adoption resources.
• Track implementation progress, usage metrics, and staff feedback, and report status to the Chief Sales Officer.
• Comply with established policies and guidelines governing data privacy,…