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To apply, please email resume, cover letter, and favorite thing to do in Chicago (one paragraph max) to: [email protected]
Apply now

We are a growing small business seeking a creative-minded business person to guide our operations, human resources and financial planning to the next level. If you have a passion for Chicago history, architecture and the Chicago River, then you are especially encouraged to apply. We are looking for someone with diverse administrative experience who wants to elevate their career. We will provide extensive training and support the educational and professional development with the chosen candidate for this full-time position with benefits.

Key Responsibilities include and are not limited to:

  • Financial Planning & Analysis: Financial planning and projection. Track and report Bookings, Revenue, and Profit against annual, quarterly and monthly goals.
  • Human Resources Management: Collaborate with Private Tour Coordinator, Marketing Coordinator, and Public Tour Coordinator to share reports that will promote growth and assist in opportunity pipeline management. Oversee payroll and benefits administration.
  • Office Operations: Analyze and organize office procedures to increase efficiency and productivity.
  • Tour Finance & Accounting: Analyze tour profit margins. Organize system for accounts payable and expenses. Reconcile labor accounting data. Provide a revenue forecast based on project assignments and schedules.
  • Billing/Invoicing/Collections: Manage freelancer who checks accuracy of billing, accounting and receivables.
  • Website Management: Oversee the work of our Webmaster. 


  • A flexible, creative, entrepreneurial spirit and a demonstrated passion for the mission and values of Chicago Detours.
  • Able to take ownership and drive activities to completion.
  • Strong verbal and written communications skills are a must, as well as the ability to work effectively across internal and external organizations with limited direction.
  • Self-motivated, action-oriented, multi-tasking individual with a sense of urgency and strong follow-through.
  • Experience in finance, business management, human resources, and sales operations in small to mid-scale companies.
  • Background in Excel and Quickbooks.
  • Strong business acumen including but not limited to: Understanding of financial statements, ability to lead Program Finance, understanding of and experience with the Tableau, advanced Excel skills.
  • BS/BA degree in business, accounting or administrative-related field. 


  • 3-7 years of experience in business management and operations with start-ups and/or established companies.
  • Proven experience optimizing project accounting and billing systems.
  • Able to operate autonomously in a fast-paced, growing small business.
  • Exhibits sound business judgment, strong analytical skills, and a proven track record of taking ownership and leading data-driven analyses to support and grow a business.
  • Experience using BI tools and CRM software.
  • Background in managing vendors on business systems implementation projects.


  • Paid vacation
  • Paid sick days
  • Health insurance
  • Dental insurance
  • CTA stipend
  • Fun, creative working environment
  • Free walking and bus tours of interior architecture, historic bars, jazz and blues, and Chicago neighborhoods
  • Flexible work schedule
  • Educational team outings
  • Office is in the beautiful and historic Monadnock Building. 

We are hiring immediately and starting interviews in February.

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To apply, please email resume, cover letter, and favorite thing to do in Chicago (one paragraph max) to: [email protected]
Apply now
To apply, please email resume, cover letter, and favorite thing to do in Chicago (one paragraph max) to: [email protected]
Apply now
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