AI Enablement Specialist

AI Enablement Specialist 

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. 

POSITION SUMMARY 

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. 

ESSENTIAL DUTIES AND RESPONSIBILITIES 

AI Enablement and Implementation (approximately 70%) 

• 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, confidentiality, and Choose Chicago operations in all AI and automation work. 

Sales & Client Services Leadership Support (approximately 30%) 

• Drafts, edits, and formats letters, memos, presentations, and other documents on behalf of Sales and Client Services leadership. 

• Assists with the creation of presentations. 

• Manages Sales and Client Services leadership's fast-paced schedules by planning and scheduling meetings, conference calls, and calendar logistics. 

• Assists leadership in the timely and seamless management of all communications, written and via telephone, email, and voicemail, with a variety of constituents. 

• Prepares leadership for weekly calendars of activities, including prioritization of meetings and inclusion of documents and meeting materials. 

• Reviews calendars and outstanding projects weekly with Sales and Client Services leadership to ensure all due preparation is completed. 

• Prepares agendas, as needed, for meetings with high-level clientele and partners. 

• Creates and distributes meeting notices and invitations on behalf of Sales and Client Services leadership. 

• Communicates professionally on behalf of Sales and Client Services leadership with staff, Board members, clients, and stakeholders. 

• On own initiative or as assigned, assists with and participates in projects, functions, and special events. 

• Performs other duties as assigned. 

MINIMUM QUALIFICATIONS 

• Bachelor's degree in Technology, Information Systems, or Business or equivalent experience required; a background in Hospitality Management, Marketing, or Communications is a plus. 

• Prior experience providing executive-level administrative support to senior leadership preferred. 

• Strong interest and foundational knowledge in artificial intelligence, emerging technologies, and digital transformation. 

• Proven project management experience with high attention to detail managing multiple, sometimes competing, priorities in a fast-paced environment. 

KNOWLEDGE, SKILLS, AND ABILITIES 

• Proficient in using workplace AI technologies and automation tools to improve efficiency while maintaining strict adherence to data privacy, confidentiality, and company policies. 

• Ability to effectively communicate both verbally and in writing with a strong knowledge of spelling, grammar, and punctuation. 

• Ability to represent Choose Chicago in a professional manner while interfacing with internal and external stakeholders; excellent telephone and interpersonal skills. 

• Ability to communicate technical concepts in approachable and practical terms to non-technical staff. 

• Superior organizational skills and attention to detail; ability to multi-task and complete multiple projects and requests simultaneously and accurately. 

• Must be able to maintain the highest level of confidentiality and discretion when handling sensitive information. 

• Exceedingly well organized, flexible, and able to work in a fast-paced environment with limited supervision. 

• Proficiency in Microsoft Office Suite, including Word, Excel, PowerPoint, and Outlook, and comfort learning new technology platforms quickly. 

PHYSICAL REQUIREMENTS AND ENVIRONMENTAL CONDITIONS 

• Ability to perform computer work for extended periods of time. 

• Ability to sit for extended periods of time in performing the work. 

• Ability to travel by ground transportation as required in performing the work.  

• Ability to work in-office a minimum of three (3) days per week.   

• Occasional evening and event work required.