Executive Assistant to CEO

I’m looking for a highly organized and proactive Executive Assistant to work directly with me and help keep several growing businesses running smoothly.

I run a group of companies in Chicago focused on architecture, construction, and real estate investments, and this role plays an important part in keeping communication, priorities, and administrative systems organized across the business.

This role is ideal for someone who enjoys bringing structure to a fast-moving environment and ensuring that nothing falls through the cracks.

RESPONSABILITIES

Executive Support

• Full ownership of the founder’s calendar and scheduling

• Daily inbox triage and drafting responses when appropriate

• Preparing documents, proposals, and reports

• Coordinating travel and logistics when needed

Business Administration

• Organizing financial, legal, and operational documentation

• Coordinating with accountants, insurance providers, and attorneys

• Tracking invoices and administrative processes

• Maintaining organized internal systems and files

Communication Coordination

• Acting as the first point of contact for vendors, tenants, and consultants

• Routing requests to the appropriate team members

• Tracking open items and following up to ensure completion

Systems & Process Improvement

• Document recurring processes and create checklists

• Help maintain organized workflows across the business

• Identify opportunities to improve administrative systems over time

Qualifications

• 3 years experience in an executive assistant, administrative, or office coordination role

• Excellent organization and communication skills

• Strong attention to detail

• Ability to manage multiple priorities independently

Experience in real estate, architecture, construction, or consulting environments is a plus, but not required.

Compensation

• Salary: $55,000 – $65,000

• Performance bonus opportunity

• Healthcare reimbursement (up to $400/month)

• PTO and paid holidays

About the Company

We are a Chicago-based group of companies focused on architecture, construction, and real estate development, primarily working on residential and multi-unit projects.

This role offers the opportunity to work directly with the founder and gain exposure to how multiple growing businesses operate.

To Apply

Please follow the instructions carefully. Applications that do not follow these steps will not be reviewed.

1. Send an email to: info@redmuginvestments.com
2. Use the following subject line exactly: Red Mug EA Application – [Your Name]
3. In the body of the email include a short paragraph answering this question: What systems or tools do you use to stay organized when managing many tasks at once?
4. Attach the following documents as PDFs:

• Your resume

• Your DISC personality profile

You can complete a free DISC assessment here:

https://discpersonalitytesting.com/free-disc-test/

Please download or save your results and attach them to the email.