Jobs at Choose Chicago

Coordinates organization-wide AI and automation initiatives with an external consultancy, supporting implementation timelines, process documentation, training, adoption, metrics, and cross-department collaboration. Provides executive administrative support to sales and client services leadership, including scheduling, communications, presentations, meeting preparation, and stakeholder coordination. The role requires strong organization, project management, communication, confidentiality, technology proficiency, and adaptability.

Leads finance operations as the CFO’s deputy, overseeing accounting, budgeting, forecasting, reporting, internal controls, cash flow, compliance, audits, and staff development. Partners with executives and departments to translate financial data into strategic recommendations, improve processes through technology and AI-enabled tools, and present to boards and stakeholders. Manages reconciliations, closing activities, expense controls, and regulatory correspondence while supporting organizational planning and financial stewardship.

Manage hotel sales development across the Midwest and Illinois corporate market, targeting mid-sized conventions and meetings. Drive room-night production and new account goals, develop market plans, close business for hotel partners, and maintain client relationships. Represent Choose Chicago at industry events, deliver presentations, achieve sales activity targets, and collaborate with internal teams. The role requires extensive travel, independent work, and in-office attendance three days weekly.