A cover letter and resume are requested by all applicants. Applications that do not include a cover letter and resume will not be considered.
The Executive Assistant (EA) to Alderman Brendan Reilly supports the daily operations of the 42nd Ward Office and helps manage the Alderman’s schedule and communications.
The EA’s primary responsibility is managing the Alderman’s calendar and invitations. This includes coordinating public events, City Council committee meetings, stakeholder meetings, and other official engagements. The EA also prepares weekly briefing memos summarizing meeting requests, invitations, and constituent concerns for the Alderman’s review.
The EA must develop a working knowledge of Chicago business licensing procedures and zoning regulations. The role involves regular coordination with business owners, developers, and community stakeholders seeking feedback or approval on proposals within the 42nd Ward. The EA works closely with the Director of Business Affairs and Development to prepare briefing materials and recommendations for the Alderman.
Additional responsibilities include monitoring ward office email accounts, responding to constituent inquiries, tracking service requests, managing meeting invitations, and escalating urgent matters. The EA also supports public events by preparing remarks for the Alderman, staffing appearances, documenting events through photography, and engaging with residents and stakeholders on behalf of the office. The position includes communications responsibilities, such as drafting and producing the ward’s weekly newsletter. The EA prepares newsletter content for the Alderman’s review and approval before publication.
During the City of Chicago budget season, the EA helps prepare departmental budget memoranda, track responses from city departments, organize budget materials, and monitor Budget Committee hearings to ensure follow-up on outstanding questions and requests. The EA also prepares materials for committee meetings, including constituent correspondence, legislative summaries, briefing documents, and other supporting materials related to agenda items.
This position requires strong organizational skills, professionalism, discretion, and responsiveness. The ideal candidate can manage competing priorities in a fast-paced government environment while maintaining effective communication with City Council staff, department officials, constituents, and community stakeholders. The position also requires flexibility, as attendance at evening meetings, community events, and occasional weekend activities will be expected.
Required Skills & Qualifications
Applicants should possess:
● Exceptional organizational and time-management skills
● Strong written and verbal communication abilities
● Professional judgment and discretion when handling sensitive information
● Experience managing complex calendars and scheduling logistics
● Ability to prioritize and respond quickly to time-sensitive matters
● Strong attention to detail and follow-through
● Excellent interpersonal skills and professionalism in public-facing situations
● Ability to synthesize large amounts of information into concise briefing materials
● Proficiency in Microsoft Office Suite, Google Workspace, and email management systems
● Ability to draft professional correspondence, memos, newsletters, and talking points
● Familiarity with municipal government, legislative processes, zoning, or licensing procedures preferred
● Experience working in government, public affairs, communications, or constituent services preferred
● Ability to work independently while coordinating across multiple stakeholders and departments
● Willingness to attend evening or weekend events as needed
The ideal candidate is highly organized, politically aware, adaptable, and committed to providing responsive and professional public service to residents of the 42nd Ward. Interested candidates should submit a resume and cover letter.
Pay: $55,000.00 - $60,000.00 per year
Benefits:
- 401(k)
- Dental insurance
- Health insurance
- Paid time off
- Retirement plan
Work Location: In person
