Executive Assistant to the CEO- Distinctive Schools

Posted on: August 9, 2023 | |

Position Title: Executive Assistant to the CEO
Location: 910 W. Van Buren, Ste. 315, Chicago, IL 60607
Reports To: CEO
Salary Range: $73,584 – $85,000
Employee Type: Regular Full Time
Start Date: August 2023

Distinctive Schools creates diverse, joyful, welcoming communities rooted in social justice and rigorous learning. We support all learners to be engaged, curious, and to achieve their full potential. Our students become confident advocates, creative problem-solvers, and collaborative leaders.

Position Description:
A Distinctive Schools Executive Assistant enhances the executives’ effectiveness by providing information management support, representing the executives to others, and managing daily functions. The Executive Assistant supports the CEO with executive-level leadership and dedicated support of appointment scheduling, travel plans, a variety of event coordination, and assisting with collaborating on administrative processes. This role will include communication and direct interaction with executive-level personnel, internal and external directors, and external collaborators.

This position also provides front counter support including, but not limited to answering phones, taking messages, directing calls, and coordinating general office operations.


Communication Management

Produce information by transcribing, formatting, inputting, editing, retrieving, copying, and transmitting text, data, and graphics
Compose effective correspondence independently and edit a wide variety of materials such as electronic correspondence, reports, contracts, forms, applications, memoranda, and other documents
Prepare and distribute selected meeting agendas and reports including research, preparation, and production of data and supportive material
Exercise considerable judgment and apply experience in making decisions; provide information in accordance with established procedures and policies; refer problems requiring technical answers to appropriate administrators
Communicate with stakeholders and proactively manage communication for the Executive; represent the executive by attending meetings in the executive’s absence; speaking for the executive
Respond to requests for information from students, staff and stakeholders regarding District programs, policies, procedures and regulations
Welcome guests and partners by greeting them, in person or on the telephone; answering or directing inquiries
Support overall office management; ensures operation of equipment by completing preventive maintenance requirements; troubleshooting malfunctions; calling for repairs; evaluating new equipment and techniques and communicating with technical team
Manage and develop Board of Directors with strong communication and leadership
Time and Calendar Management

Maintain executive’s appointment schedule by planning and scheduling meetings, conferences, teleconferences, and travel; maintains professional development and internal network calendars
Conserve executive’s time by reading, researching, and routing correspondence; drafting letters and documents; collecting and analyzing information; initiating
Lead travel oversight, scheduling and planning
Manage external travel, lodging and event partners identifying cost saving opportunities and efficiencies
Data Management

Maintain confidence and protect operations by keeping all information confidential; responds to questions by the media and/or community
Secure information by completing database backups
Provide historical reference by developing and utilizing filing and retrieval systems; recording meeting discussions
Maintain professional and technical knowledge by attending educational workshops; reviewing professional publications; establishing personal networks
Train and provide work direction to departmental staff as assigned; monitor office workflow and assure compliance with established time lines, procedures and standards of quality

Plan and develop events, trainings, conferences and professional development sessions
Develop, organize and conduct training sessions with internal and external partners to ensure compliance with District policy, process and procedure
Support the preparation and oversight of selected grants


Education: High School Diploma


At least 2 year of office administration experience
Ability to work under pressure and in a highly sensitive environment
Exceptional oral and written communication skills
Interpersonal skills using tact, patience, and courtesy
Strong organizational and problem-solving skills and proactive workstyle
Strong multi-tasking and prioritization skills
Ability and willingness to be available outside of the typical 8-5 business hours
Technology demands:
Proficient with cloud based computer software (Google Docs, Google Sheets, and Google Slides)
Operate computer proficiently using advanced text processing, spreadsheet and database software to enter, manipulate, format, and retrieve information
Physical demands

Occasional lifting, carrying, pushing, and/or pulling; some stooping, kneeling, crouching, and/or crawling; and significant fine finger dexterity. Generally, the job requires 70% sitting, 20% walking, and 10% standing.


25+ Paid holidays & 15 days PTO annually
12 weeks family paid leave
Comprehensive Healthcare (Medical, Dental, Vision)
403b match
Fully match up to 3%
50% match up to 5%
Professional development including tuition reimbursement
Gym and wellness discounts
And more
Job Description Disclaimer: Since no job description can detail all the duties and responsibilities that may be required from time to time in the performance of a job, duties and responsibilities that may be inherent in a job, reasonably required for its performance, or required due to the changing nature of the job shall also be considered part of the jobholder’s responsibility.

EEO: Distinctive Schools is an equal opportunity employer and does not discriminate against any employee or applicant for employment on the basis of race, color, religion, sex, gender, national origin, age, disability, veteran status, marital status, sexual orientation, gender identity, gender expression, or any other personal characteristic protected by applicable law.
Distinctive Schools is committed to the full inclusion of all qualified individuals. In keeping with our commitment, Distinctive Schools will take the steps to assure that people with disabilities are provided reasonable accommodations. Accordingly, if reasonable accommodation is required to fully participate in the job application or interview process, to perform the essential functions of the position, and/or to receive all other benefits and privileges of employment, please contact or call 773.828.4191