Executive Assistant in Chicago, IL (IN PERSON, hiring ASAP)

Executive & Personal Assistant to Entrepreneur

Location: Bucktown, Chicago (In-Person)

Schedule: Monday–Friday | 8:00 AM–4:00 PM or 9:00 AM–5:00 PM

Compensation

Up to $100,000 annually (commensurate with experience)

Benefits

Health insurance stipend, 401(k) match, paid time off, and additional benefits

About the Opportunity

We are seeking a highly experienced Executive & Personal Assistant to become the trusted right hand to busy entrepreneur and his wife. This is a dynamic role for someone who thrives in a fast-paced environment, anticipates needs before they arise, and enjoys balancing both executive operations and personal support.

The ideal candidate is polished, proactive, exceptionally organized, and understands how to bring order to busy, high-performing lives. This is not an entry-level assistant position—we're looking for someone who has built systems, managed competing priorities, and can confidently keep executives operating at their highest level.

This position supports both founders with responsibilities divided approximately as follows:

• 50% Business Operations & Executive Support
• 30% Personal Support for Principal
• 20% Personal Support for wife
• What You'll Do

Executive Support

• Manage complex calendars and scheduling
• Coordinate meetings, travel, and business logistics
• Screen communications and prioritize competing demands
• Prepare meeting materials, presentations, and correspondence
• Track projects and ensure deadlines are met
• Build and improve organizational systems and workflows
• Act as a trusted liaison with clients, vendors, and business partners
• Anticipate needs and solve problems before they arise

Personal Assistance

• Coordinate personal appointments and household logistics
• Run local errands, including returns, pickups, car washes and coffee runs
• Assist with reservations, gifting, and special projects
• Manage personal scheduling and administrative tasks
• Handle confidential information with the highest level of discretion

Who You Are

You are the type of assistant who doesn't wait to be told what to do—you already have the next step planned.

You have worked with executives before and understand that your role is to remove obstacles, create efficiency, and keep everything moving seamlessly.

You are

• Highly proactive and resourceful
• Exceptionally organized with outstanding attention to detail
• Warm, personable, and confident interacting with clients and executives
• Comfortable managing both business and personal responsibilities
• Able to remain calm under pressure and shift priorities quickly
• Professional, discreet, and trustworthy
• Comfortable creating systems rather than simply following them
• Able to communicate clearly and confidently

About the Principals

You'll primarily support one entrepreneur and his wife with different working styles.

Wife is kind, collaborative, and approachable.

Main principle has high expectations, communicates directly, and values efficiency. He appreciates people who are confident, resilient, and solutions-oriented. A thick skin and the ability to remain composed under pressure are important for success in this role.

What We're Looking For

• Several years of experience supporting C-suite executives, founders, or entrepreneurs
• Strong background in executive assistance and project coordination
• Excellent written and verbal communication skills
• Outstanding organizational and time management abilities
• Ability to anticipate needs rather than simply react to requests
• Professional demeanor with exceptional client-facing skills
• Proficiency with modern business technology and productivity tools
• Valid driver's license and reliable transportation for local errands

Schedule & Flexibility

This is an in-office role based in Bucktown, Monday through Friday.

Typical hours are

• 8:00 AM–4:00 PM or
• 9:00 AM–5:00 PM

While work-life balance is valued, occasional flexibility to respond to an urgent text or email outside of business hours is appreciated.

Interview Process

Our interview process is designed to identify exceptional assistants.

He has a direct communication style and will challenge candidates during the interview. We're looking for someone who can remain composed, think critically, and demonstrate confidence under pressure. If you enjoy working with ambitious entrepreneurs and excel in fast-paced environments, this role offers the opportunity to become an indispensable part of a growing business.

If you're someone who is always one step ahead, loves bringing order to complexity, and enjoys making a meaningful impact every day, we'd love to hear from you.